Information on EC 1.14.11.9 - flavanone 3-dioxygenase:
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EC NUMBERCOMMENTARY
1.14.11.9-

RECOMMENDED NAMEGeneOntology No.
flavanone 3-dioxygenaseGO:0045486

REACTIONREACTION DIAGRAMCOMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
a flavanone + 2-oxoglutarate + O2 = a dihydroflavonol + succinate + CO2
show the reaction diagram		----
a flavanone + 2-oxoglutarate + O2 = a dihydroflavonol + succinate + CO2
show the reaction diagram		enzyme catalyzes double-bond formation by direct abstraction of vicinal hydrogen atoms at C-2 and C-3 of the substratePetroselinum crispum-439113

REACTION TYPEORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
oxidation----
redox reaction----
reduction----

PATHWAYKEGG LinkMetaCyc Link
flavonoid biosynthesis-PWY1F-FLAVSYN
flavonoid biosynthesis (in equisetum)-PWY-6787
leucopelargonidin and leucocyanidin biosynthesis-PWY1F-823
pinobanksin biosynthesis-PWY-5059

SYSTEMATIC NAMEIUBMB Comments
flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)Requires Fe2+ and ascorbate.

SYNONYMSORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
(2S)-flavanone 3-hydroxylase----
F3H----
F3HCitrus sinensisQ9ZWR0-671524
F3HMalus x domestica, Pyrus communis--676671
F3HGlycine maxQ53B69-700130
F3HGlycine soja--700130
F3HSecale cerealeC7S853-700225
F3HVitis viniferaP41090-700742
F3HRhododendron x pulchrumA9ZMJ3-701213
F3HSolanum lycopersicum--713238
F3HSorghum bicolorD2Y4P1-713256
F3H proteinVitis viniferaP41090-700742
FHTPetroselinum crispumQ7XZQ7-655572
FHTPetunia x hybrida--658733
FHTFragaria x ananassa--674117
FHTMalus x domestica--675792, 676671
FHTPyrus communis--676671
FHTPrunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra--698431
FHTPH----
flavanone 3-dioxygenasePrunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra--698431
flavanone 3-hydroxylase----
flavanone 3-hydroxylaseCitrus x paradisi, Petunia sp.--660098
flavanone 3-hydroxylaseFragaria x ananassa--674117
flavanone 3-hydroxylasePrunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra--698431
flavanone 3-hydroxylaseGlycine maxQ53B69-700130
flavanone 3-hydroxylaseGlycine soja--700130
flavanone 3-hydroxylaseSecale cerealeC7S853-700225
flavanone 3-hydroxylaseVitis viniferaP41090-700742
flavanone 3-hydroxylaseRhododendron x pulchrumA9ZMJ3-701213
flavanone 3-hydroxylaseSolanum lycopersicum--713238
flavanone 3-hydroxylaseSorghum bicolorD2Y4P1-713256
flavanone 3beta-hydroxylase----
flavanone 3beta-hydroxylasePetroselinum crispumQ7XZQ7-655572
flavanone 3beta-hydroxylasePetunia x hybrida--658733
flavanone 3beta-hydroxylaseCitrus sinensisQ9ZWR0-671524
flavanone 3beta-hydroxylaseMalus x domestica--675792, 676671
flavanone 3beta-hydroxylasePyrus communis--676671
flavanone synthase I----
flavanone-3-hydroxylaseRubus arcticus--700308
FS I----
naringenin 3-dioxygenase----
naringenin,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)----
oxygenase, flavanone 3-di-----

CAS REGISTRY NUMBERCOMMENTARY
75991-43-4-

ORGANISMCOMMENTARYLITERATURESEQUENCE CODESEQUENCE DB SOURCE
Antirrhinum majus-439001, 439126--Manually annotated by BRENDA team
Arabidopsis thaliana-439128, 689653--Manually annotated by BRENDA team
Callistephus chinensis-439126--Manually annotated by BRENDA team
Camellia sinensis-690168Q6DV45UniProtManually annotated by BRENDA team
Camellia sinensis var. sinensiscultivar Oolong No. 17700794Q6DV45UniProtManually annotated by BRENDA team
Citrus sinensis-671524Q9ZWR0TrEMBLManually annotated by BRENDA team
Citrus x paradisi-660098--Manually annotated by BRENDA team
Dahlia pinnataenzyme is present in cyanic strain, absent in acyanic strain439120--Manually annotated by BRENDA team
Dianthus caryophyllus-439126--Manually annotated by BRENDA team
Fragaria x ananassa-674117--Manually annotated by BRENDA team
Glandularia x hybridaenzyme is present in cyanic strain, absent in acyanic strain439120--Manually annotated by BRENDA team
Glycine maxcv. Wye, 33 Chinese soybean accessions including 16 Glycine soja and 17 Glycine max700130Q53B69UniProtManually annotated by BRENDA team
Glycine maxexpression is induced by ultraviolet-B irradiation688942--Manually annotated by BRENDA team
Glycine soja33 Chinese soybean accessions including 16 Glycine soja and 17 Glycine max700130--Manually annotated by BRENDA team
Hordeum vulgare-439126--Manually annotated by BRENDA team
Malus x domestica-675792--Manually annotated by BRENDA team
Malus x domesticacultivars M9 and Weirouge676671--Manually annotated by BRENDA team
Matthiola incana-438998, 439006, 439126--Manually annotated by BRENDA team
Medicago sativa-439122--Manually annotated by BRENDA team
no activity in Actinidia deliciosagreen-fleshed cultivar Hayward; kiwi fruit, cultivar Hayward, ripe fruit and leaves698431--Manually annotated by BRENDA team
Oryza sativaisoform OsF3H-1688943--Manually annotated by BRENDA team
Oryza sativaisoform OsF3H-2688943Q8W2X5UniProtManually annotated by BRENDA team
Oryza sativaisoform OsF3H-3688943Q7XR84UniProtManually annotated by BRENDA team
Petroselinum crispum-439113, 689577--Manually annotated by BRENDA team
Petroselinum crispumcv. Italian Giant655572Q7XZQ7SwissProtManually annotated by BRENDA team
Petunia sp.-660098--Manually annotated by BRENDA team
Petunia x hybrida-439114, 439119, 439124, 439125, 439126, 439127, 658733--Manually annotated by BRENDA team
Prunus aviumcultivar Augustkirsche, cherry; cv. Augustkirsche698431--Manually annotated by BRENDA team
Prunus cerasuscultivar Pandy 114, sour cherry; cv. Pandy 114698431--Manually annotated by BRENDA team
Prunus domestica; plum698431--Manually annotated by BRENDA team
Pyrus communiscultivars Pyrodwarf and Conference676671--Manually annotated by BRENDA team
Rhododendron x pulchrum-701213A9ZMJ3UniProtManually annotated by BRENDA team
Ribes uva-crispa; gooseberry698431--Manually annotated by BRENDA team
Rubus arcticuscv. Mespi700308--Manually annotated by BRENDA team
Rubus fruticosus; blackberry698431--Manually annotated by BRENDA team
Rubus idaeus; raspberry698431--Manually annotated by BRENDA team
Sambucus nigra; elder698431--Manually annotated by BRENDA team
Secale cerealefragment; rye Imperial and Monstrous700225C7S853UniProtManually annotated by BRENDA team
Sinapis alba-439116--Manually annotated by BRENDA team
Solanum lycopersicum-439123--Manually annotated by BRENDA team
Solanum lycopersicumstructural gene F3H713238--Manually annotated by BRENDA team
Solanum lycopersicum Suzannestructural gene F3H713238--Manually annotated by BRENDA team
Sorghum bicolortwo structural genes SbF3H1 and SbF3H2713256D2Y4P1UniProtManually annotated by BRENDA team
Streptocarpus hybridaenzyme is present in cyanic strain, absent in acyanic strain439120--Manually annotated by BRENDA team
Tulipa hybrid cultivarc.v. Apeldoorn439115--Manually annotated by BRENDA team
Vitis viniferaL. cv. Cabernet Sauvignon700742P41090UniProtManually annotated by BRENDA team
Zinnia violaceaenzyme is present in cyanic strain, absent in acyanic strain439120--Manually annotated by BRENDA team

GENERAL INFORMATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
metabolismRhododendron x pulchrumA9ZMJ3part of flavonoid biosynthetic pathway701213
metabolismSolanum lycopersicum-the enzyme is involved in the flavonoid and phenylpropanoid biosynthesis pathway, overview713238
physiological functionSorghum bicolorD2Y4P1flavanone 3-hydroxylase converts flavanones to dihydroflavonols for anthocyanin biosynthesis, F3H is a key flavonoid structural gene713256
metabolismSorghum bicolorD2Y4P1flavanone 3-hydroxylase converts flavanones to dihydroflavonols for anthocyanin biosynthesis713256
additional informationSorghum bicolorD2Y4P1in Sorghum seedlings, expression of the two F3H genes is either absent or strongly suppressed during the accumulation of 3-deoxyanthocyanidins713256

SUBSTRATEPRODUCT                      REACTION DIAGRAMORGANISM UNIPROT ACCESSION NO. COMMENTARY/
Substrate		 LITERATURE/
Substrate		 COMMENTARY/
Product		 LITERATURE/
Product		 Reversibility
r=reversible
ir=irreversible
?=not specified
(2S)-flavanone + 2-oxoglutarate + O2(2R/3R)-dihydroflavonol + succinate + CO2
show the reaction diagram		Petunia x hybrida-key step towards biosynthesis of flavonols, anthocyanins and catechins658733--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Petroselinum crispum--439113, 689577--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Oryza sativaQ7XR84, Q8W2X5-688943--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Tulipa hybrid cultivar--439115--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Petunia x hybrida--439119-439119?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Malus x domestica--675792--ir
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Matthiola incana--439006--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Petunia x hybrida-His220, His278 and Asp222 are part of the 2-oxoglutarate binding site439124--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Glycine max-90% of the activity with eriodictyol688942--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Arabidopsis thaliana-enzyme is stereospecific for (S)-naringenin689653--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Camellia sinensisQ6DV45reaction is stereospecific690168--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Glycine soja-F3H700130--?
(2S)-naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Glycine maxQ53B69F3H700130--?
(S)-eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Oryza sativaQ7XR84, Q8W2X5-688943--?
3'-methoxy eriodictyol + 2-oxoglutarate + O2? + succinate + CO2
show the reaction diagram		Oryza sativaQ7XR84, Q8W2X5-688943--?
3'-methoxy eriodictyol + 2-oxoglutarate + O2? + succinate + CO2
show the reaction diagram		Glycine max-16% of the activity with eriodictyol688942--?
3'-methoxy eriodictyol + 2-oxoglutarate + O2? + succinate + CO2
show the reaction diagram		Oryza sativaQ7XR84, Q8W2X568% of the activity with eriodictyol688943--?
4'-methoxy eriodictyol + 2-oxoglutarate + O2? + succinate + CO2
show the reaction diagram		Oryza sativaQ7XR84, Q8W2X5-688943--?
4'-methoxy eriodictyol + 2-oxoglutarate + O2? + succinate + CO2
show the reaction diagram		Oryza sativaQ7XR84, Q8W2X5105% of the activity with eriodictyol688943--?
4'-methoxy eriodictyol + 2-oxoglutarate + O2? + succinate + CO2
show the reaction diagram		Glycine max-56% of the activity with eriodictyol688942--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Glycine max--688942--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Petroselinum crispum--439113--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Fragaria x ananassa--674117--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Malus x domestica--676671--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Malus x domestica--675792--ir
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Pyrus communis--676671--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Matthiola incana--439006--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Tulipa hybrid cultivar-50% of the activity with naringenin439115--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Petunia x hybrida-(2S)-eriodictyol439119-439119?
naringenin + 2-oxoadipate + O2dihydrokaempferol + pentanedioate + CO2
show the reaction diagram		Petunia x hybrida--439124-439124?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Prunus avium, Rubus fruticosus--698431--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Petunia x hybrida--658733--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Fragaria x ananassa--674117--ir
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Prunus domestica--698431--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Malus x domestica, Pyrus communis--676671--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Rubus idaeus, Sambucus nigra--698431--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Citrus sinensisQ9ZWR0-671524--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Prunus cerasus, Ribes uva-crispa--698431--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Sinapis alba-induction of the enzyme by light439116--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Matthiola incana-enzyme is involved in anthocyanin biosynthesis438998--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Solanum lycopersicum-enzyme is involved in anthocyanin pathway439123---
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Dahlia pinnata, Zinnia violacea-enzyme is involved in anthocyanin pathway439120--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Matthiola incana-enzyme is involved in anthocyanin pathway438998--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Glandularia x hybrida, Streptocarpus hybrida-enzyme is involved in anthocyanin pathway439120--?
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Arabidopsis thaliana-the F3H gene is coordinately expressed with chalcone synthase and chalcone isomerase in seedlings. The F3H gene may represent a pivotal point in the regulation of flavonoid biosynthesis439128---
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Petunia x hybrida-enzyme is involved in the biosynthesis of flavonoids, catechins, and anthocyanidins439124, 439125--?
naringenin + 2-oxoglutarate + O2dihydrokaempferol + succinate + CO2
show the reaction diagram		Solanum lycopersicum--713238--?
naringenin + O2 + 2-oxoglutaratedihydrokaempferol + succinate + CO2
show the reaction diagram		Prunus avium-0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris-HCl, pH 7.5, containing 0.4% sodium ascorbate)698431--?
naringenin + O2 + 2-oxoglutaratedihydrokaempferol + succinate + CO2
show the reaction diagram		Rubus fruticosus, Prunus domestica, Rubus idaeus, Sambucus nigra, Prunus cerasus, Ribes uva-crispa-0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)698431--?
pinocembrin + 2-oxoglutarate + O2?
show the reaction diagram		Petunia x hybrida-38% of the activity with naringenin658733--?
eriodictyol + 2-oxoglutarate + O2(2R,3R)-dihydroquercitin + succinate + CO2
show the reaction diagram		Petunia x hybrida-95% of the activity with naringenin658733--?
additional information?-Petroselinum crispum-no activity with (+)-dihydrokaempferol and (2R)-naringenin439113---
additional information?-Petunia x hybrida-no activity with (2R)-naringenin and 5,7,3',4',5'-pentahydroxyflavanone439119---
additional information?-Camellia sinensis var. sinensisQ6DV45involved in catechin biosynthesis700794---
additional information?-Prunus avium, Rubus fruticosus, Prunus domestica, Rubus idaeus, Sambucus nigra, Prunus cerasus, Ribes uva-crispa-two different protocols for enzyme preparation from eight fruit species698431---

NATURAL SUBSTRATESNATURAL PRODUCTSREACTION DIAGRAMORGANISM UNIPROT ACCESSION NO.COMMENTARY SUBSTRATELITERATURE
(Substrate)		COMMENTARY PRODUCTLITERATURE
(Product)
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Sinapis alba-induction of the enzyme by light439116--
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Matthiola incana-enzyme is involved in anthocyanin biosynthesis438998--
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Solanum lycopersicum-enzyme is involved in anthocyanin pathway439123--
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Dahlia pinnata, Zinnia violacea-enzyme is involved in anthocyanin pathway439120--
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Matthiola incana-enzyme is involved in anthocyanin pathway438998--
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Glandularia x hybrida, Streptocarpus hybrida-enzyme is involved in anthocyanin pathway439120--
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Arabidopsis thaliana-the F3H gene is coordinately expressed with chalcone synthase and chalcone isomerase in seedlings. The F3H gene may represent a pivotal point in the regulation of flavonoid biosynthesis439128--
naringenin + 2-oxoglutarate + O2(2R,3R)-dihydrokaempferol + succinate + CO2
show the reaction diagram		Petunia x hybrida-enzyme is involved in the biosynthesis of flavonoids, catechins, and anthocyanidins439124, 439125--
naringenin + 2-oxoglutarate + O2dihydrokaempferol + succinate + CO2
show the reaction diagram		Solanum lycopersicum--713238--
naringenin + O2 + 2-oxoglutaratedihydrokaempferol + succinate + CO2
show the reaction diagram		Prunus avium-0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris-HCl, pH 7.5, containing 0.4% sodium ascorbate)698431--
naringenin + O2 + 2-oxoglutaratedihydrokaempferol + succinate + CO2
show the reaction diagram		Rubus fruticosus, Prunus domestica, Rubus idaeus, Sambucus nigra, Prunus cerasus, Ribes uva-crispa-0.046 nmol 14C-labeled substrate, 3.48 mM 2-oxoglutarate, 5 mM FeSO4 * 7 H2O, buffer (0.1 M Tris/HCl, pH 7.5, containing 0.4% sodium ascorbate)698431--
(2S)-flavanone + 2-oxoglutarate + O2(2R/3R)-dihydroflavonol + succinate + CO2
show the reaction diagram		Petunia x hybrida-key step towards biosynthesis of flavonols, anthocyanins and catechins658733--
additional information?-Camellia sinensis var. sinensisQ6DV45involved in catechin biosynthesis700794--
additional information?-Prunus avium, Rubus fruticosus, Prunus domestica, Rubus idaeus, Sambucus nigra, Prunus cerasus, Ribes uva-crispa-two different protocols for enzyme preparation from eight fruit species698431--

COFACTORORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATUREIMAGE
2-oxoglutaratePrunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra--698431 2D-image
ascorbateMalus x domestica, Pyrus communis-required676671 2D-image
ascorbateOryza sativaQ7XR84, Q8W2X5; ; 688943 2D-image
ascorbatePrunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra--698431 2D-image
hemePrunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra--698431 2D-image

METALS and IONS ORGANISM UNIPROT ACCESSION NO.COMMENTARY LITERATURE
Co2+Petunia x hybrida-can partially replace Fe2+439119
Fe2+Matthiola incana-required439006
Fe2+Petroselinum crispum-required439113
Fe2+Tulipa hybrid cultivar--439115
Fe2+Petunia x hybrida-required439119, 439124
Fe2+Malus x domestica, Pyrus communis-required676671
Fe2+Prunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra--698431
IronPetunia x hybrida-non-heme iron protein. His220, His278 and Asp222 constitute three of the possible ligands for iron binding in the active site of the enzyme439124
IronGlycine max--688942

INHIBITORSORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
(+)-dihydrokaempferolPetunia x hybrida-product inhibition439119 2D-image
3-Bromo-2-oxoglutaratePetunia x hybrida-1 mM 92% inhibition439119 2D-image
3-hydroxy-5-oxo-4-butyryl-cyclohex-3-ene-1-carboxylic acid ethyl esterMalus x domestica, Pyrus communis-1 mM 36% relative activity, 0.1 mM 68% relative activity676671 2D-image
3-hydroxy-5-oxo-4-cyclopropanecarbonyl-cyclohex-3-ene-1-carboxylic acid ethyl esterMalus x domestica, Pyrus communis-1 mM 9% relative activity, 0.1 mM 38% relative activity676671 2D-image
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-(2-dimethylamino)-thiazoleMalus x domestica, Pyrus communis-1 mM 25% relative activity, 0.1 mM 56% relative activity676671 2D-image
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carbaldehydeMalus x domestica, Pyrus communis-1 mM 33% relative activity, 0.1 mM 75% relative activity676671 2D-image
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carbothioic acid S-ethyl esterMalus x domestica, Pyrus communis-1 mM 15% relative activity, 0.1 mM 40% relative activity676671 2D-image
3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-pentanoic acidMalus x domestica, Pyrus communis-1 mM 13% relative activity, 0.1 mM 75% relative activity676671 2D-image
benzene-1,2,4,5-tetracarboxylic acidMalus x domestica, Pyrus communis-1 mM 95% relative activity676671 2D-image
calcium 3-hydroxy-5-oxo-4-propionyl-cyclohex-3-ene-1-carboxylateMalus x domestica, Pyrus communis-1 mM 10% relative activity, 0.1 mM 33% relative activity676671 2D-image
Cu2+Petroselinum crispum-in presence of 0.01 mM Fe2+439113 2D-image
Cu2+Petunia x hybrida--439119 2D-image
DiethyldicarbonateMatthiola incana-0.5 mM, 15% inhibition; slight439006 2D-image
DiethyldicarbonateTulipa hybrid cultivar-0.5 mM, 10% inhibition; 2 mM, complete inhibition; slight439115 2D-image
DiethyldicarbonatePetunia x hybrida-ascorbate protects against inactivation439124 2D-image
DiethyldicarbonateMatthiola incana, Petunia x hybrida--439126 2D-image
diethyldithiocarbamateMatthiola incana-2 mM, complete inhibition439006 2D-image
diethyldithiocarbamatePetunia x hybrida-2 mM, 81% inhibition439119 2D-image
diethyldithiocarbamateDahlia pinnata, Glandularia x hybrida, Streptocarpus hybrida, Zinnia violacea--439120 2D-image
EDTAMatthiola incana-1 mM, 75% inhibition439006 2D-image
EDTATulipa hybrid cultivar-2 mM, complete inhibition439115 2D-image
EDTAPetunia x hybrida-1 mM, 21% inhibition439119 2D-image
EDTADahlia pinnata, Glandularia x hybrida, Streptocarpus hybrida, Zinnia violacea--439120 2D-image
EDTAOryza sativaQ7XR84, Q8W2X50.2 M, complete loss of activity; 0.2 M, complete loss of activity; 0.2 M, complete loss of activity688943 2D-image
Fe3+Petunia x hybrida-1 mM, 56% inhibition439119 2D-image
KCNMatthiola incana-5 mM, complete inhibition439006 2D-image
KCNTulipa hybrid cultivar-5 mM, 72% inhibition439115 2D-image
KCNPetunia x hybrida-1 mM, 11% inhibition439119 2D-image
KCNDahlia pinnata, Glandularia x hybrida, Streptocarpus hybrida, Zinnia violacea--439120 2D-image
p-chloromercuribenzoateMatthiola incana-0.1 mM, 5% inhibition439006 2D-image
p-chloromercuribenzoateTulipa hybrid cultivar-no inhibition439115 2D-image
p-chloromercuribenzoatePetunia x hybrida-1 mM, 91% inhibition439119 2D-image
Pyridine-2,4-dicarboxylatePetroselinum crispum-most potent competitive inhibitor439113 2D-image
Pyridine-2,4-dicarboxylatePetunia x hybrida-0.002 mM, 50% inhibition439119 2D-image
pyridine-2,4-dicarboxylic acid diethyl esterMalus x domestica, Pyrus communis-1 mM 7% relative activity, 0.1 mM 21% relative activity676671 2D-image
Pyridine-2,5-dicarboxylatePetunia x hybrida-0.01 mM, 40% inhibition439119 2D-image
pyridine-2,5-dicarboxylic acidMalus x domestica, Pyrus communis-1 mM 3% relative activity, 0.1 mM 11% relative activity676671 2D-image
sodium 4,6-dioxo-2,2-dimethyl-5-(1-alloxyamino-butylidene)-cyclohexane-1-carboxylic acid methyl esterMalus x domestica, Pyrus communis-1 mM 89% relative activity676671 2D-image
Zn2+Petroselinum crispum-in presence of 0.01 mM Fe2+439113 2D-image

ACTIVATING COMPOUNDORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
ascorbateMatthiola incana-required439006 2D-image
ascorbatePetroselinum crispum-required439113 2D-image
ascorbatePetunia x hybrida-required439119 2D-image
piperazine-1,4-bis-(2-ethane sulfonic acid)Pyrus communis-1 mM, 96% relative activity676671 2D-image
piperazine-1,4-bis-(2-ethane sulphonic acid)Malus x domestica-1 mM, 96% relative activity676671 2D-image
pyridine-2,3-dicarboxylic acidMalus x domestica, Pyrus communis-1 mM 205% relative activity, 0.1 mM 120% relative activity676671 2D-image
pyridine-2,6-dicarboxylic acidMalus x domestica, Pyrus communis-1 mM 220% relative activity, 0.1 mM 186% relative activity676671 2D-image
pyridine-2,6-dicarboxylic acid chlorideMalus x domestica, Pyrus communis-1 mM, 196% relative activity, 0.1 mM 194% relative activity676671 2D-image
pyrrole-3,4-dicarboxylic acid diethyl esterMalus x domestica, Pyrus communis-1 mM, 113% relative activity676671 2D-image
sodium 4,6-dioxo-2,2-dimethyl-5-(1-alloxyamino-butylidene)-cyclohexane-1-carboxylic acid methyl esterMalus x domestica, Pyrus communis-0.1 mM 115% relative activity676671 2D-image
catalasePetunia x hybrida-stimulates439119-
additional informationVitis viniferaP41090sugars induce anthocyanin accumulation and flavanone 3-hydroxylase expression in grape berries. Glucosamine and mannoheptulose, the specific inhibitors of hexokinase, block the activation induced by sugar on both anthocyanin accumulation and F3H expression700742-

KM VALUE [mM]KM VALUE [mM] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
0.008-(2S)-eriodictyolPetroselinum crispum--439113 2D-image
0.012-(2S)-eriodictyolPetunia x hybrida--439119 2D-image
0.005-(2S)-naringeninPetroselinum crispum--439113 2D-image
0.0056-(2S)-naringeninPetunia x hybrida--439119 2D-image
0.024-(2S)-naringeninArabidopsis thaliana-25°C689653 2D-image
0.0057-(S)-eriodictyolOryza sativaQ7XR84, Q8W2X5pH 8.0, 37°C688943 2D-image
0.0063-(S)-eriodictyolOryza sativaQ7XR84, Q8W2X5pH 8.0, 37°C688943 2D-image
0.0578-(S)-eriodictyolOryza sativaQ7XR84, Q8W2X5pH 8.0, 37°C688943 2D-image
1.4-2-oxoadipatePetunia x hybrida--439124 2D-image
0.0019-2-oxoglutaratePetunia x hybrida-wild-type enzyme439125 2D-image
0.016-2-oxoglutaratePetroselinum crispum-reaction with naringenin439113 2D-image
0.02-2-oxoglutaratePetunia x hybrida-reaction with naringenin439119 2D-image
0.0256-2-oxoglutaratePetunia x hybrida-mutant enzyme S290T439125 2D-image
0.08-2-oxoglutaratePetunia x hybrida-mutant enzyme S290A439125 2D-image
0.1896-2-oxoglutaratePetunia x hybrida-mutant enzyme S290V439125 2D-image
0.087-eriodictyolGlycine max-pH 8.0, 37°C688942 2D-image
additional information-additional informationPetunia x hybrida-varying Km-values, depending on the purification procedure439119-
additional information-additional informationPetunia x hybrida-Km-values of mutant enzymes439124-

TURNOVER NUMBER [1/s] TURNOVER NUMBER MAXIMUM[1/s] SUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

kcat/KM VALUE [1/mMs-1]kcat/KM VALUE [1/mMs-1] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

Ki VALUE [mM]Ki VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
0.0012-Pyridine 2,4-dicarboxylatePetunia x hybrida--439119 2D-image
0.0018-Pyridine 2,4-dicarboxylatePetroselinum crispum--439113 2D-image
0.04-Pyridine 2,5-dicarboxylatePetunia x hybrida--439119 2D-image

IC50 VALUE [mM]IC50 VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

SPECIFIC ACTIVITY [µmol/min/mg] SPECIFIC ACTIVITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
2.6e-06-Sambucus nigra-unripe fruit: 43 nkat/kg total protein (enzyme extraction protocol 2)698431
3.8e-06-Sambucus nigra-flower: 64 nkat/kg total protein (enzyme extraction protocol 1)698431
7.9e-06-Ribes uva-crispa-ripe fruit: 131 nkat/kg total protein (enzyme extraction protocol 2), no activity with enzyme extraction protocol 1698431
1.2e-05-Ribes uva-crispa-unripe fruit: 196 nkat/kg total protein (enzyme extraction protocol 1)698431
1.2e-05-Rubus fruticosus-leaves: 198 nkat/kg total protein (enzyme extraction protocol 1); leaves: 198 nkat/kg total protein (enzyme extraction protocol 2)698431
1.5e-05-Sambucus nigra-unripe fruit: 242 nkat/kg total protein (enzyme extraction protocol 1)698431
1.9e-05-Prunus domestica-leaves: 316 nkat/kg total protein (enzyme extraction protocol 1), no activity with enzyme extraction protocol 2698431
2.1e-05-Prunus avium-ripe fruit: 357 nkat/kg total protein (enzyme extraction protocol 2)698431
2.3e-05-Rubus fruticosus-ripe fruit: 388 nkat/kg total protein (enzyme extraction protocol 1)698431
2.6e-05-Rubus fruticosus-unripe fruit: 440 nkat/kg total protein (enzyme extraction protocol 2), no activity with enzyme extraction protocol 1698431
2.7e-05-Rubus fruticosus-ripe fruit: 443 nkat/kg total protein (enzyme extraction protocol 2)698431
2.8e-05-Sambucus nigra-flower: 46 nkat/kg total protein (enzyme extraction protocol 2)698431
2.9e-05-Sambucus nigra-ripe fruit: 484 nkat/kg total protein (enzyme extraction protocol 2)698431
3.6e-05-Prunus avium-leaves: 606 nkat/kg total protein (enzyme extraction protocol 2)698431
4.1e-05-Sambucus nigra-leaves: 690 nkat/kg total protein (enzyme extraction protocol 1), no activity with enzyme extraction protocol 2; ripe fruit: 688 nkat/kg total protein (enzyme extraction protocol 1)698431
4.5e-05-Prunus avium-leaves: 758 nkat/kg total protein (enzyme extraction protocol 1)698431
5e-05-Prunus domestica-unripe fruit: 833 nkat/kg total protein (enzyme extraction protocol 2), no activity with enzyme extraction protocol 1698431
5.6e-05-Prunus avium-ripe fruit: 932 nkat/kg total protein (enzyme extraction protocol 1)698431
6.2e-05-Ribes uva-crispa-unripe fruit: 1039 nkat/kg total protein (enzyme extraction protocol 2)698431
6.6e-05-Rubus idaeus-leaves: 1105 nkat/kg total protein (enzyme extraction protocol 2), no activity with enzyme extraction protocol 1698431
9.2e-05-Rubus idaeus-ripe fruit: 1537 nkat/kg total protein (enzyme extraction protocol 2), no activity with enzyme extraction protocol 1698431
0.00012-Ribes uva-crispa-leaves: 1933 nkat/kg total protein (enzyme extraction protocol 2), no activity with enzyme extraction protocol 1698431
0.00026-Prunus cerasus-unripe fruit: 4400 nkat/kg total protein (enzyme extraction protocol 2), no activity with enzyme extraction protocol 1698431
0.0009-Prunus cerasus-ripe fruit: 15072 nkat/kg total protein (enzyme extraction protocol 1)698431
0.00094-Prunus cerasus-ripe fruit: 15652 nkat/kg total protein (enzyme extraction protocol 2)698431
0.032-Camellia sinensisQ6DV45-690168
25-Arabidopsis thaliana-25°C689653
additional information-Matthiola incana--439006
additional information-Petroselinum crispum--439113
additional information-Petunia x hybrida--439114, 439119, 439124
additional information-Prunus cerasus-no activity in leaves, whether with enzyme extraction protocol 1 or 2698431
additional information-Prunus domestica-no activity in ripe fruit, whether with enzyme extraction protocol 1 or 2698431
additional information-Rubus idaeus-no activity in unripe fruit, whether with enzyme extraction protocol 1 or 2698431

pH OPTIMUMpH MAXIMUMORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
6-Petunia x hybrida-wild-type enzyme, and second lower optimum at pH 8.0439124
7.25-Malus x domestica, Pyrus communis--676671
7.5-Tulipa hybrid cultivar--439115
8.58.6Petroselinum crispum--439113
8.58.7Arabidopsis thaliana--689653
8.5-Petunia x hybrida--439119
additional information-Petunia x hybrida-pH-optima of mutant enzymes439124

pH RANGEpH RANGE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

TEMPERATURE OPTIMUMTEMPERATURE OPTIMUM MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
30-Malus x domestica, Pyrus communis--676671
40-Arabidopsis thaliana--689653

TEMPERATURE RANGE TEMPERATURE MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pI VALUEpI VALUE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SOURCE TISSUE ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE SOURCE
antherTulipa hybrid cultivar-tapetum-bound439115Manually annotated by BRENDA team
budMatthiola incana--438998Manually annotated by BRENDA team
flowerMatthiola incana--438998, 439006Manually annotated by BRENDA team
flowerAntirrhinum majus--439001Manually annotated by BRENDA team
flowerDahlia pinnata, Glandularia x hybrida, Streptocarpus hybrida, Zinnia violacea--439120Manually annotated by BRENDA team
flowerMedicago sativa--439122Manually annotated by BRENDA team
flowerSambucus nigra--698431Manually annotated by BRENDA team
flower budCallistephus chinensis, Dianthus caryophyllus, Matthiola incana--439126Manually annotated by BRENDA team
flower budCitrus x paradisi, Petunia sp.-high level of mRNA expression660098Manually annotated by BRENDA team
fruitFragaria x ananassa--674117Manually annotated by BRENDA team
fruitPrunus avium-; ripe fruit698431Manually annotated by BRENDA team
fruitPrunus cerasus-; ripe and unripe (50% size, uncolored)698431Manually annotated by BRENDA team
fruitPrunus domestica, Ribes uva-crispa-no activity in ripe fruits; ripe and unripe (50% size, uncolored)698431Manually annotated by BRENDA team
fruitRubus fruticosus-; ripe and unripe (50% size, uncolored)698431Manually annotated by BRENDA team
fruitRubus idaeus-no activity in unripe fruits; ripe and unripe (50% size, uncolored)698431Manually annotated by BRENDA team
fruitSambucus nigra-; ripe and unripe (50% size, uncolored)698431Manually annotated by BRENDA team
fruitVitis viniferaP41090-700742Manually annotated by BRENDA team
hypocotylSolanum lycopersicum--439123Manually annotated by BRENDA team
leafPetroselinum crispumQ7XZQ7immature655572Manually annotated by BRENDA team
leafCitrus x paradisi-high level of expression in primary leaves of 32 day old seedlings660098Manually annotated by BRENDA team
leafPetunia sp.-high level of expression in primary leaves of 65 day old seedlings660098Manually annotated by BRENDA team
leafMalus x domestica, Pyrus communis--676671Manually annotated by BRENDA team
leafCamellia sinensisQ6DV45positive correlation between the concentration of catechins and the expression of flavonol 3-hydroxylase in different developmental stages. Expression is down-regulated in response to drought and gibberellic acid treatment, but up-regulated in response to wounding690168Manually annotated by BRENDA team
leafPrunus avium-; young, enrolling leaves698431Manually annotated by BRENDA team
leafPrunus cerasus-young, enrolling leaves698431Manually annotated by BRENDA team
leafPrunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra-; young, enrolling leaves698431Manually annotated by BRENDA team
leafRubus arcticus-detectable only in benzothiadiazole-treated plant700308Manually annotated by BRENDA team
leafCamellia sinensis var. sinensisQ6DV45mature700794Manually annotated by BRENDA team
leafRhododendron x pulchrumA9ZMJ3low amount701213Manually annotated by BRENDA team
noduleMatthiola incana--438998Manually annotated by BRENDA team
petalRhododendron x pulchrumA9ZMJ3-701213Manually annotated by BRENDA team
rootMatthiola incana--438998Manually annotated by BRENDA team
rootCitrus x paradisi--660098Manually annotated by BRENDA team
rootPetunia sp.-high level of expression in roots of 65 day old seedlings660098Manually annotated by BRENDA team
seedOryza sativaQ7XR84, Q8W2X5highest expression; highest expression; highest expression688943Manually annotated by BRENDA team
seedlingSinapis alba-enzyme shows a drastic increase in activity after illumination and reaches a maximum at the time of rapid anthocyanin accumulation439116Manually annotated by BRENDA team
seedlingArabidopsis thaliana-etiolated439128Manually annotated by BRENDA team
seedlingSorghum bicolorD2Y4P1-713256Manually annotated by BRENDA team
sepalRhododendron x pulchrumA9ZMJ3-701213Manually annotated by BRENDA team
shootCamellia sinensis var. sinensisQ6DV45higher accumulation700794Manually annotated by BRENDA team
stamenRhododendron x pulchrumA9ZMJ3-701213Manually annotated by BRENDA team
stemCitrus x paradisi, Petunia sp.--660098Manually annotated by BRENDA team
leafSolanum lycopersicum--713238Manually annotated by BRENDA team
additional informationPrunus avium-protein content of the enzyme in the different plants and tissue preparations obtained with two different protocols698431Manually annotated by BRENDA team
additional informationPrunus cerasus-no activity in leaves, protein content of the enzyme in the different plants and tissue preparations obtained with two different protocols698431Manually annotated by BRENDA team
additional informationPrunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra-protein content of the enzyme in the different plants and tissue preparations obtained with two different protocols698431Manually annotated by BRENDA team

LOCALIZATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY GeneOntology No. LITERATURE SOURCE
solubleAntirrhinum majus---439001Manually annotated by BRENDA team
solubleMatthiola incana---439006Manually annotated by BRENDA team
solubleDahlia pinnata, Glandularia x hybrida, Streptocarpus hybrida, Zinnia violacea---439120Manually annotated by BRENDA team
solublePetunia x hybrida---439124, 439125Manually annotated by BRENDA team

PDBSCOPCATHORGANISM
No entries in this field

MOLECULAR WEIGHT MOLECULAR WEIGHT MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
39200-Petunia x hybrida-sedimentation equilibrium analysis439127
41000-Vitis viniferaP41090SDS-PAGE700742
48000-Petroselinum crispum-gel filtration439113
74000-Petunia x hybrida-gel filtration439119

SUBUNITS ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
?Petunia x hybrida-x * 35000 + x * 37000, two-dimensional SDS-PAGE439119
?Hordeum vulgare-x * 43600, calculation from nucleotide sequence439126
?Matthiola incana-x * 40000, calculation from nucleotide sequence439126
?Petunia x hybrida--439126
?Glycine max-x * 42700, calculated, x * 68000, SDS-PAGE of fusion protein with glutathione S-transferase688942
?Oryza sativaQ7XR84, Q8W2X5x * 36800, calculated; x * 38700, calculated; x * 42700, calculated688943
?Vitis viniferaP41090x * 41000, SDS-PAGE700742
dimerPetroselinum crispum-2 * 24000-25000, SDS-PAGE439113
additional informationPetunia x hybrida-enzyme exists as functional monomeric and oligomeric forms. The monomeric polypeptide comprises the catalytically active flavanone 3beta-hydroxylase439127

POSTTRANSLATIONAL MODIFICATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

Crystallization/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

pH STABILITYpH STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

TEMPERATURE STABILITYTEMPERATURE STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
30-Arabidopsis thaliana-stable up to689653

GENERAL STABILITYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

ORGANIC SOLVENT ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

OXIDATION STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
partially stabilized under anaerobic conditions in presence of ascorbatePetunia x hybrida-439119

STORAGE STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-70°C, in presence of 20 mM ascorbate, stable for more than 6 monthsPetunia x hybrida-439119

Purification/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
Sephadex G25 column gel filtrationFragaria x ananassa-674117
-Glycine maxQ53B69700130
-Glycine soja-700130
-Petroselinum crispum-439113
-Petunia x hybrida-439114, 439119, 439124
recombinant enzymePetunia x hybrida-439126
wild-type and mutant enzymesPetunia x hybrida-439125, 658733
shock frozen fruits are ground in a mill, leaves are ground in liquid nitrogen in a mortar, protocol 1: plant material is homogenized in a mortar with quartz sand and Polyclar AT with extraction buffer (0.1 M Tris-HCl, pH 7.5, containing 0.4% sodium ascorbate) and centrifuged, or protocol 2 (optimized for polyphenol-rich tissues): plant material is homogenized with Polyclar AT in a mortar, transferred to a falcon tube containing Dowex in buffer (0.7 M KH2PO4/K2HPO4, pH 8.0, containing 0.4 M sucrose, 0.4 M sodium ascorbate, 1 mM CaCl2, 30 mM EDTA, 50 mM cysteine, 50 mM DIECA, 1.5% PEG 20000, and 0.1% BSA, kept under nitrogen atmosphere after removing oxygen by boiling), homogenate is filtered (glass wool) and centrifuged, supernatants obtained with both protocols are cleared of low molecular compounds by a Sephadex G25 gel chromatography columnPrunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus-698431
shock frozen fruits are ground in a mill, leaves are ground in liquid nitrogen in a mortar, protocol 1: plant material is homogenized in a mortar with quartz sand and Polyclar AT with extraction buffer (0.1 M Tris-HCl, pH 7.5, containing 0.4% sodium ascorbate) and centrifuged, or protocol 2 (optimized for polyphenol-rich tissues): plant material is homogenized with Polyclar AT in a mortar, transferred to a falcon tube containing Dowex in buffer (0.7 M KH2PO4/K2HPO4, pH 8.0, containing 0.4 M sucrose, 0.4 M sodium ascorbate, 1 mM CaCl2, 30mM EDTA, 50 mM cysteine, 50 mM DIECA, 1.5% PEG 20000, and 0.1% BSA, kept under nitrogen atmosphere after removing oxygen by boiling), homogenate is filtered (glass wool) and centrifuged, supernatants obtained with both protocols are cleared of low molecular compounds by a Sephadex G25 gel chromatography columnSambucus nigra-698431

Cloned/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-Arabidopsis thaliana-439128
expression in a reticulocyte systemCallistephus chinensis-439126
expression in Escherichia coliCamellia sinensisQ6DV45690168
expressed in Escherichia coli strain BLR (DE3)Citrus sinensisQ9ZWR0671524
expression in a reticulocyte systemDianthus caryophyllus-439126
cloned into the pGEM T-easy plasmid vector and transformed into DH5alpha Escherichia coli competent cellsGlycine maxQ53B69700130
expression in Escherichia coliGlycine max-688942
cloned into the pGEM T-easy plasmid vector and transformed into DH5alpha Escherichia coli competent cellsGlycine soja-700130
expressed in Escherichia coli BL21Star and Rosetta(DE3) cellsMalus x domestica-675792
expressed in yeast strain InvSc1Malus x domestica-676671
-Matthiola incana-439126
expression as glutathione S-transferase fusion protein; expression as glutathione S-transferase fusion protein; expression as glutathione S-transferase fusion proteinOryza sativaQ7XR84, Q8W2X5688943
-Petroselinum crispumQ7XZQ7655572
expression in Saccharomyces cerevisiaePetroselinum crispum-689577
expression in Escherichia coliPetunia x hybrida-658733
wild-type and mutant enzymes, expression in Escherichia coliPetunia x hybrida-439124, 439125
expressed in yeast strain InvSc1Pyrus communis-676671
expression in Escherichia coli JM109Rhododendron x pulchrumA9ZMJ3701213
expression in wheat-rye hybridsSecale cerealeC7S853700225
enzyme expression analysis by real-time RT-PCRSolanum lycopersicum-713238
genes SbF3H1 and SbF3H2, semi-quantitative RT-PCR expression analysis of flavonoid structural genes in sorghum seedlings, overview. Complementation of Arabidopsis thaliana flavonoid mutants by genes SbF3H1 and SbF3H2, complementation analysis, overviewSorghum bicolorD2Y4P1713256

EXPRESSION ORGANISM UNIPROT ACCESSION NO. LITERATURE
decrease at stage of floweringRhododendron x pulchrumA9ZMJ3701213
flavanone 3-hydroxylase expression increases in response to N depletion, in agreement with a corresponding increase in flavonoid and caffeoyl content in tomato leaves, and/or to lower temperatures, overview. The effects of N depletion are apparently mediated through the overall regulators of the pathway the MYB transcription factor ANT1, ANTHOCYANIN 1, and SlJAF13, a bHLH transcription factor orthologue of petunia JAF13 and maize RED genesSolanum lycopersicum-713238
no induction of the SbF3H1 and SbF3H2 genes by methyljasmonateSorghum bicolorD2Y4P1713256

ENGINEERINGORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
D195EPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
D195E/L215V/K216RPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
D331HPetroselinum crispum-no catalytic activity689577
I115TPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
I115T/V116IPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
I115T/V116I/I131F/D195EPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is converted to 76% flavanone 3beta-hydroxylase product dihydrokaempferol and to 24% flavone synthase product apigenin689577
I131FPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
I131F/D195EPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
I131F/D195E/L215V/K216RPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is converted to 69% flavanone 3beta-hydroxylase product dihydrokaempferol and to 31% flavone synthase product apigenin689577
I131F/L215V/K216RPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is converted to 78% flavanone 3beta-hydroxylase product dihydrokaempferol and to 22% flavone synthase product apigenin689577
L215V/K216RPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
M106TPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is completely converted to flavanone 3beta-hydroxylase product dihydrokaempferol689577
M106T/I115T/V116I/I131F/D195EPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is converted to 66% flavanone 3beta-hydroxylase product dihydrokaempferol and to 34% flavone synthase product apigenin689577
M106T/I115T/V116I/I131F/D195E/L215V/K216RPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is converted to 18% flavanone 3beta-hydroxylase product dihydrokaempferol and to 82% flavone synthase product apigenin689577
H220QPetunia x hybrida-catalytic activity is reduced to about 0.15% of that of the wild-type enzyme. Slightly increased Km-value with respect to iron binding, as compared to the wild-type enzyme439124
N222NPetunia x hybrida-catalytic activity is reduced to about 0.15% of that of the wild-type enzyme. Slightly increased Km-value with respect to iron binding, as compared to the wild-type enzyme439124
R288KPetunia x hybrida-decrease in catalytic activity and a 5fold increase in Km-value for 2-oxoglutarate439124
R288QPetunia x hybrida-decrease in catalytic activity and a 160fold increase in Km-value for 2-oxoglutarate439124
S290APetunia x hybrida-activity is reduced to 8% of that of the wild-type enzyme439125
S290TPetunia x hybrida-activity is reduced to 20% of that of the wild-type enzyme439125
S290VPetunia x hybrida-activity is reduced to 1% of that of the wild-type enzyme439125
additional informationArabidopsis thaliana-in mutants lacking flavanone 3beta-hydroxylase, the enzymes flavonol synthase EC 1.14.11.23, and anthocyanidin synthase, EC 1.14.11.19, can partially compensate for its activity in vivo689653
M106T/I131F/D195EPetroselinum crispum-mutant constructed to confer flavone synthase activity to flavanone 3beta-hydroxylase. Substrate naringenin is converted to 85% flavanone 3beta-hydroxylase product dihydrokaempferol and to 15% flavone synthase product apigenin689577
additional informationPetroselinum crispum-domain swapping experiments joining the N-terminus of flavanone 3beta-hydroxylase with the C-terminus of flavone synthase I and vice versa. Active site residues of flavanone 3beta-hydroxylase are M106, I115, V116, I131, D195, V200, L215, and K216689577
H278QPetunia x hybrida-mutant enzyme has no detectable enzyme activity439124
additional informationPetunia x hybrida-four C-terminally truncated enzyme forms are generated by deletion of five, 11, 24 or 29 amino acids. The recombinant enzymes preserve their substrate electrivity, but the specific activity decreases gradually with the extent of truncation. An enzyme chimera is constructed by domain swapping replacing the C-terminal 52 amino acids of the Petunia enzyme by equivalent region of flavonol synthase from Citrus unshiu658733

Renatured/COMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

APPLICATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
agricultureGlycine maxQ53B69the aim is to identify the soybean mosaic virus resistance associated single nucleotide polymorphism in the IFS1, IFS2 and F3H gene by association mapping in order to develop valuable genetic markers for future soybean mosaic virus resistance breeding efforts in soybean700130
agricultureGlycine soja-the aim is to identify the soybean mosaic virus resistance associated single nucleotide polymorphism in the IFS1, IFS2 and F3H gene by association mapping in order to develop valuable genetic markers for future soybean mosaic virus resistance breeding efforts in soybean700130
agricultureVitis viniferaP41090basis for further research on the control of berry skin color and wine quality700742
additional informationCamellia sinensis var. sinensisQ6DV45F3H gene may be used as biomarker in tea breeding programs and genetic engineering to improve tea quality700794

REF. AUTHORS TITLE JOURNAL VOL. PAGES YEAR ORGANISMLINK TO PUBMEDSOURCE
438998Dangelmayr, B.; Stotz, G.; Spribille, R.; Forkmann, G.Relationship between flower development, anthocyanin accumulation and activity of enzymes involved in flavonoid biosynthesis in Matthiola incana R.Br.Z. Naturforsch. C38551-5551983Matthiola incana-
439001Forkmann, G.; Stotz, G.Genetic control of flavanone 3-hydroxylase activity and flavonoid 3'-hydroxylase activity in Antirrhinum majus (Snapdragon)Z. Naturforsch. C36411-4161981Antirrhinum majus-
439006Forkmann, G.; Heller, W.; Grisebach, H.Anthocyanin biosynthesis in flowers of Matthiola incana flavanone 3- and flavonoid 3'-hydroxylasesZ. Naturforsch. C35691-6951980Matthiola incana-
439113Britsch, L.Purification and characterization of flavone synthase I, a 2-oxoglutarate-dependent desaturaseArch. Biochem. Biophys.282152-1601990Petroselinum crispum PubMed
439114Britsch, L.Purification of flavanone 3 beta-hydroxylase from Petunia hybrida: antibody preparation and characterization of a chemogenetically defined mutantArch. Biochem. Biophys.276348-3541990Petunia x hybrida PubMed
439115Beerhues, L.; Forkmann, G.; Schoepker, H.; Stotz, G.; Wiermann, R.Flavanone 3-hydroxylase and dihydroflavonol oxygenase activities in anthers of Tulipa. The significance of the tapetum fraction in flavonoid metabolismJ. Plant Physiol.133743-7461989Tulipa hybrid cultivar-
439116Takeda, K.; Fischer, D.; Grisebach, H.Anthocyanin composition of Sinapis alba, light induction of enzymes and biosynthesisPhytochemistry271351-13531988Sinapis alba-
439119Britsch, L.; Grisebach, H.Purification and characterization of (2S)-flavanone 3-hydroxylase from Petunia hybridaEur. J. Biochem.156569-5771986Petunia x hybrida PubMed
439120Forkmann, G.; Stotz, G.Selection and characterisation of flavanone 3-hydroxylase mutants of Dahlia, Streptocarpus, Verbena and ZinniaPlanta161261-2651984Dahlia pinnata, Glandularia x hybrida, Streptocarpus hybrida, Zinnia violacea-
439122Charrier, B.; Coronado, C.; Kondorosi, A.; Ratet, P.Molecular characterization and expression of alfalfa (Medicago sativa L.) flavanone-3-hydroxylase and dihydroflavonol-4-reductase encoding genesPlant Mol. Biol.29773-7861995Medicago sativa PubMed
439123O'Neill, S.D.; Tong, Y.; Spoerlein, B.; Forkmann, G.; Yoder, J.I.Molecular genetic analysis of chalcone synthase in Lycopersicon esculentum and an anthocyanin-deficient mutantMol. Gen. Genet.224279-2881990Solanum lycopersicum PubMed
439124Lukacin, R.; Britsch, L.Identification of strictly conserved histidine and arginine residues as part of the active site in Petunia hybrida flavanone 3beta-hydroxylaseEur. J. Biochem.249748-7571997Petunia x hybrida PubMed
439125Lukacin, R.; Groning, I.; Pieper, U.; Matern, U.Site-directed mutagenesis of the active site serine290 in flavanone 3beta-hydroxylase from Petunia hybridaEur. J. Biochem.267853-8602000Petunia x hybrida PubMed
439126Britsch, L.; Dedio, J.; Saedler, H.; Forkmann, G.Molecular characterization of flavanone 3 beta-hydroxylases. Consensus sequence, comparison with related enzymes and the role of conserved histidine residuesEur. J. Biochem.217745-7541993Antirrhinum majus, Callistephus chinensis, Dianthus caryophyllus, Hordeum vulgare, Matthiola incana, Petunia x hybrida PubMed
439127Lukacin, R.; Urbanke, C.; Groning, I.; Matern, U.The monomeric polypeptide comprises the functional flavanone 3beta-hydroxylase from Petunia hybridaFEBS Lett.467353-3582000Petunia x hybrida PubMed
439128Pelletier, M.K.; Shirley, B.W.Analysis of flavanone 3-hydroxylase in Arabidopsis seedlings. Coordinate regulation with chalcone synthase and chalcone isomerasePlant Physiol.111339-3451996Arabidopsis thaliana PubMed
655572Martens, S.; Forkmann, G.; Britsch, L.; Wellmann, F.; Matern, U.; Lukacin, R.Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsleyFEBS Lett.54493-982003Petroselinum crispum PubMed
658733Wellmann, F.; Matern, U.; Lukacin, R.Significance of C-terminal sequence elements for Petunia flavanone 3beta-hydroxylase activityFEBS Lett.561149-1542004Petunia x hybrida PubMed
660098Pelt, J.L.; Downes, W.A.; Schoborg, R.V.; McIntosh, C.A.Flavanone 3-hydroxylase expression in Citrus paradisi and Petunia hybrida seedlingsPhytochemistry64435-4442003Citrus x paradisi, Petunia sp. PubMed
671524Miyahisa, I.; Funa, N.; Ohnishi, Y.; Martens, S.; Moriguchi, T.; Horinouchi, S.Combinatorial biosynthesis of flavones and flavonols in Escherichia coliAppl. Microbiol. Biotechnol.7153-582006Citrus sinensis PubMed
674117Halbwirth, H.; Puhl, I.; Haas, U.; Jezik, K.; Treutter, D.; Stich, K.Two-phase flavonoid formation in developing strawberry (Fragaria x ananassa) fruitJ. Agric. Food Chem.541479-14852006Fragaria x ananassa PubMed
675792Leonard, E.; Yan, Y.; Koffas, M.A.Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coliMetab. Eng.8172-1812006Malus x domestica PubMed
676671Halbwirth, H.; Fischer, T.C.; Schlangen, K.; Rademacher, W.; Schleifer, K.; Forkmann, G.; Stich, K.Screening for inhibitors of 2-oxoglutarate-dependent dioxygenases: Flavanone 3b-hydroxylase and flavonol synthasePlant Sci.171194-2052006Malus x domestica, Pyrus communis-
688942Kim, B.G.; Kim, J.H.; Kim, J.; Lee, C.; Ahn, J.H.Accumulation of flavonols in response to ultraviolet-B irradiation in soybean is related to induction of flavanone 3-beta-hydroxylase and flavonol synthaseMol. Cell25247-2522008Glycine max PubMed
688943Kim, J.H.; Lee, Y.J.; Kim, B.G.; Lim, Y.; Ahn, J.H.Flavanone 3beta-hydroxylases from rice: key enzymes for favonol and anthocyanin biosynthesisMol. Cell25312-3162008Oryza sativa PubMed
689577Gebhardt, Y.H.; Witte, S.; Steuber, H.; Matern, U.; Martens, S.Evolution of flavone synthase I from parsley flavanone 3beta-hydroxylase by site-directed mutagenesisPlant Physiol.1441442-14542007Petroselinum crispum PubMed
689653Owens, D.K.; Crosby, K.C.; Runac, J.; Howard, B.A.; Winkel, B.S.Biochemical and genetic characterization of Arabidopsis flavanone 3beta-hydroxylasePlant Physiol. Biochem.46833-8432008Arabidopsis thaliana PubMed
690168Singh, K.; Rani, A.; Kumar, S.; Sood, P.; Mahajan, M.; Yadav, S.K.; Singh, B.; Ahuja, P.S.An early gene of the flavonoid pathway, flavanone 3-hydroxylase, exhibits a positive relationship with the concentration of catechins in tea (Camellia sinensis)Tree Physiol.281349-13562008Camellia sinensis PubMed
698431Halbwirth, H.; Waldner, I.; Miosic, S.; Ibanez, M.; Costa, G.; Stich, K.Measuring flavonoid enzyme activities in tissues of fruit speciesJ. Agric. Food Chem.574983-49872009no activity in Actinidia deliciosa, Prunus avium, Prunus cerasus, Prunus domestica, Ribes uva-crispa, Rubus fruticosus, Rubus idaeus, Sambucus nigra PubMed
700130Cheng, H.; Yang, H.; Zhang, D.; Gai, J.; Yu, D.Polymorphisms of soybean isoflavone synthase and flavanone 3-hydroxylase genes are associated with soybean mosaic virus resistanceMol. Breed.2513-242009Glycine max, Glycine soja-
700225Khlestkina, E.K.; Tereshchenko, O.Y.; Salina, E.A.Anthocyanin biosynthesis genes location and expression in wheat-rye hybridsMol. Genet. Genomics282475-4852009Secale cereale PubMed
700308Hukkanen, A.; Kokko, H.; Buchala, A.; Haeyrinen, J.; Kaerenlampi, S.Benzothiadiazole affects the leaf proteome in arctic bramble (Rubus arcticus)Mol. Plant Pathol.9799-8082008Rubus arcticus PubMed
700742Zheng, Y.; Tian, L.; Liu, H.; Pan, Q.; Zhan, J.; Huang, W.Sugars induce anthocyanin accumulation and flavanone 3-hydroxylase expression in grape berriesPlant Growth Regul.58251-2602009Vitis vinifera-
700794Eungwanichayapant, P.D.; Popluechai, S.Accumulation of catechins in tea in relation to accumulation of mRNA from genes involved in catechin biosynthesisPlant Physiol. Biochem.4794-972009Camellia sinensis var. sinensis PubMed
701213Nakatsuka, A.; Mizuta, D.; Kii, Y.; Miyajima, I.; Kobayashi, N.Isolation and expression analysis of flavonoid biosynthesis genes in evergreen azaleaSci. Hortic.118314-3202008Rhododendron x pulchrum-
713238Lovdal, T.; Olsen, K.M.; Slimestad, R.; Verheul, M.; Lillo, C.Synergetic effects of nitrogen depletion, temperature, and light on the content of phenolic compounds and gene expression in leaves of tomatoPhytochemistry71605-6132010Solanum lycopersicum PubMed
713256Liu, H.; Du, Y.; Chu, H.; Shih, C.H.; Wong, Y.W.; Wang, M.; Chu, I.K.; Tao, Y.; Lo, C.Molecular dissection of the pathogen-inducible 3-deoxyanthocyanidin biosynthesis pathway in sorghumPlant Cell Physiol.511173-11852010Sorghum bicolor PubMed

LINKS TO OTHER DATABASES (specific for EC-Number 1.14.11.9)
ExplorEnz
ExPASy
KEGG
MetaCyc
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)