Information on EC 5.5.1.6 - chalcone isomerase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
5.5.1.6
-
RECOMMENDED NAME
GeneOntology No.
chalcone isomerase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
A chalcone = a flavanone
show the reaction diagram
-
-
-
-
A chalcone = a flavanone
show the reaction diagram
rate limiting step is an intramolecular Michael addition of a 2-oxyanion to the alpha,beta-double bond. Computational study shows that the active site conformation with larger catalytic power presents a positively charged lysine resiude much closer to the substrate than the second active site. Charge is transferred from the 2-oxyanion to the beta-carbon atom
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
elimination/addition
-
-
intramolecular
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
echinatin biosynthesis
-
Flavonoid biosynthesis
-
flavonoid biosynthesis
-
flavonoid biosynthesis (in equisetum)
-
isoflavonoid biosynthesis I
-
Metabolic pathways
-
naringenin biosynthesis (engineered)
-
pinobanksin biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
flavanone lyase (decyclizing)
-
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Chalcone isomerase
-
-
-
-
Chalcone isomerase
A9ZMJ9
-
Chalcone-flavanone isomerase
-
-
-
-
CHI
-
-
-
-
CHI
C3VPI9
-
CHI
Citrus unshiu Guoqing No. 4 satsuma
C3VPI9
-
-
CHI
Haemophilus influenzae RD
-
-
-
CHI
-
gene name
CHI
Lupinus luteus Polo
-
gene name
-
CHI
P28012
-
CHI
D6MPE5
-
CHI
Pseudomonas fluorescens PfO-1
-
-
-
CHI1A
Q93XE6
-
CHI1B2
Q53B70
-
CHI2
Q53B74
-
Isomerase, chalcone
-
-
-
-
TRANSPARENT TESTA 5 protein
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
9073-57-8
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
fragment; variant mongholicus
UniProt
Manually annotated by BRENDA team
Chinese kale, cultivars Jianyexia and Zhonghua
-
-
Manually annotated by BRENDA team
isoenzyme I and II
-
-
Manually annotated by BRENDA team
Citrus unshiu Guoqing No. 4 satsuma
-
UniProt
Manually annotated by BRENDA team
gene GbCHI
-
-
Manually annotated by BRENDA team
strain T586, expression is developmentally co-regulated
SwissProt
Manually annotated by BRENDA team
Gossypium hirsutum T586
strain T586, expression is developmentally co-regulated
SwissProt
Manually annotated by BRENDA team
Haemophilus influenzae RD
RD
-
-
Manually annotated by BRENDA team
gene CHI
-
-
Manually annotated by BRENDA team
Lupinus luteus Polo
gene CHI
-
-
Manually annotated by BRENDA team
synonym Morella rubra, Chinese bayberry
D6MPE5
UniProt
Manually annotated by BRENDA team
no activity in Stenocereus thurberi
-
-
-
Manually annotated by BRENDA team
variant Gower Ramsay
UniProt
Manually annotated by BRENDA team
Opuntia sp.
-
-
-
Manually annotated by BRENDA team
line V30
-
-
Manually annotated by BRENDA team
mutants, mutation in the Po-gen has no quantitative effect on enzyme activity
-
-
Manually annotated by BRENDA team
strain PfO-1
-
-
Manually annotated by BRENDA team
Pseudomonas fluorescens PfO-1
strain PfO-1
-
-
Manually annotated by BRENDA team
pv. syringae B728a
-
-
Manually annotated by BRENDA team
Soja hispida
-
-
-
Manually annotated by BRENDA team
gene TFGCHI-1
-
-
Manually annotated by BRENDA team
cv. 'Apeldoorn'
-
-
Manually annotated by BRENDA team
RIMD 2210633
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
evolution
G3CRC0, -
SbCHI is evolutionarily related to type I CHIs
evolution
-
GbCHI belongs to the chalcone superfamily, phylogenetic tree, overview
metabolism
A9ZMJ9
part of flavonoid biosynthetic pathway
metabolism
-
chalcone isomerase is one of the key enzymes in the flavonoid biosynthesis pathway catalyzing the stereospecific isomerization of chalcones into their corresponding (2S)-flavanones
physiological function
G3CRC0, -
importance of CHI in flavone biosynthesis
physiological function
-
CHI as a key gene regulating flavonoid accumulation in ginkgo leaves
physiological function
-
CHI converts chalcones into the corresponding flavanones by selectively binding an ionized chalcone in a conformation conducive to ring closure in a diffusion controlled reaction, thus accelerating the stereochemically defined intramolecular cyclization reaction yielding a biologically active (S)-isomer
metabolism
-
CHI catalyzes the first step in flavonoid biosynthesis pathway, overview
additional information
G3CRC0, -
efficiency of metabolic engineering in hairy roots, overview
additional information
-
effects of cross-talk interactions of sucrose and infection caused by a pathogenic fungus Fusarium oxysporum f.sp. lupini on the regulation of the phenylpropanoid pathway, i.e. the level of expression of genes encoding enzymes participating in flavonoid biosynthesis, as well as cell location and accumulation of these compounds in embryo axes of Lupinus luteus L. cv. Polo, overview
additional information
Lupinus luteus Polo
-
effects of cross-talk interactions of sucrose and infection caused by a pathogenic fungus Fusarium oxysporum f.sp. lupini on the regulation of the phenylpropanoid pathway, i.e. the level of expression of genes encoding enzymes participating in flavonoid biosynthesis, as well as cell location and accumulation of these compounds in embryo axes of Lupinus luteus L. cv. Polo, overview
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E)-3-(2-fluorophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-2-(2-fluorophenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
-
based on substrate (2E)-3-(2-fluorophenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
(2E)-3-(2-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-5,7-dihydroxy-2-(2-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
-
based on substrate (2E)-3-(2-hydroxyphenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
(2E)-3-(3-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-5,7-dihydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
-
based on substrate (2E)-3-(3-hydroxyphenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
(2E)-3-(4-aminophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-2-(4-aminophenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
-
based on substrate (2E)-3-(4-aminophenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
(2E)-3-(4-fluorophenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2R)-2-(4-fluorophenyl)-5,7-dihydroxy-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
-
based on substrate (2E)-3-(4-fluorophenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
show the reaction diagram
-
based on substrate (2E)-3-(4-hydroxyphenyl)acrylic acid in combinatorial expression system of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase
-
-
?
2',4',6'-Trihydroxychalcone
?
show the reaction diagram
-
-
-
-
-
2',4'-Dihydroxy-4-methoxychalcone
?
show the reaction diagram
-
-
-
-
-
2',4'-Dihydroxy-4-methoxychalcone
?
show the reaction diagram
-
no activity
-
-
-
2',4'-dihydroxy-4-methylchalcone
7-hydroxy-2-(4-methyl-phenyl)-chroman-4-one
show the reaction diagram
Q53B70, Q53B74, Q93XE6
-
-
-
?
2',4'-Dihydroxychalcone
?
show the reaction diagram
Soja hispida
-
-
-
-
-
2',4'-dihydroxychalcone
7-hydroxy-2-phenyl-chroman-4-one
show the reaction diagram
Q53B70, Q53B74, Q93XE6
-
-
-
?
2',4-dihydroxychalcone
?
show the reaction diagram
P28012
-
-
?
2'-Hydroxy-4-methoxychalcone
?
show the reaction diagram
-
-
-
-
-
2'-Hydroxy-4-methoxychalcone
?
show the reaction diagram
-
no activity
-
-
-
2'-hydroxychalcone
2-phenyl-chroman-4-one
show the reaction diagram
Q53B70, Q53B74, Q93XE6
-
-
-
?
4,2',4',6'-tetrahydrochalcone
?
show the reaction diagram
P28012
-
-
?
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
-
-
-
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
-
-
-
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
-
-
-
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
Soja hispida
-
-
-
-
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
-
-
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
-
-
-
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
-
-
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
B2KK57, -
-
-
-
?
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
D6MPE5
-
-
-
?
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
-
i.e. naringenin
-
4,2',4',6'-Tetrahydroxychalcone
5,7,4'-Trihydroxyflavanone
show the reaction diagram
-
i.e. naringenin chalcone
-
-
4,2',4',6'-tetrahydroxychalcone
5,7-dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-one
show the reaction diagram
Q53B70, Q53B74, Q93XE6
-
-
-
?
4,2',4'-trihydrochalcone
?
show the reaction diagram
P28012
-
-
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
-
-
-
-
-
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
Soja hispida
-
-
-
-
-
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
B2KK57, -
-
-
-
?
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
-
-
the product is liquiritigenin
-
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
-
-
highly stereoselective product formation
-
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
-
no activity
-
-
-
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
-
no activity
-
-
-
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
-
i.e. isoliquiritigenin
the product is liquiritigenin
-
4,2',4'-trihydroxychalcone
(2S)-4',7-dihydroxyflavanone
show the reaction diagram
-
r, at pH 7.6
the product is liquiritigenin
-
4,2',4'-trihydroxychalcone
7-hydroxy-2-(4-hydroxy-phenyl)-chroman-4-one
show the reaction diagram
Q53B70, Q53B74, Q93XE6
-
-
-
?
4,2',5'-trihydroxychalcone
6-hydroxy-2-(4-hydroxy-phenyl)-chroman-4-one
show the reaction diagram
Q53B70, Q53B74, Q93XE6
-
-
-
?
4,2'-dihydrochalcone
?
show the reaction diagram
P28012
-
-
?
4,2'-dihydroxychalcone
2-(4-hydroxy-phenyl)-chroman-4-one
show the reaction diagram
Q53B70, Q53B74, Q93XE6
-
-
-
?
6'-deoxychalcone
?
show the reaction diagram
-
-
-
?
6'-deoxychalcone
?
show the reaction diagram
-
-
-
-
?
6'-deoxychalcone
?
show the reaction diagram
-
two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
-
?
6'-hydroxychalcone
?
show the reaction diagram
-, Q3HNP7
-
-
-
?
6'-hydroxychalcone
?
show the reaction diagram
-
two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone, two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
-
?
butein
butin
show the reaction diagram
-
-
-
-
?
Chalcone
Flavanone
show the reaction diagram
-
-
-
-
?
Chalcone
Flavanone
show the reaction diagram
Soja hispida
-
-
-
-
chalcone
naringenin
show the reaction diagram
A7KTI4, -
-
-
-
?
chalcone
(2S)-flavanone
show the reaction diagram
-
-
-
-
?
naringenin chalcone
naringenin
show the reaction diagram
-
-
-
-
?
naringenin chalcone
naringenin
show the reaction diagram
-
i.e. 6'-hydroxychalcone
-
-
?
naringenin chalcone
naringenin
show the reaction diagram
-
i.e. 6'-hydroxychalcone
-
-
?
naringenin chalcone
(2S)-naringenin
show the reaction diagram
-
naringenin chalcone (6'-hydroxychalcone) is the only substrate
-
-
?
isoliquiritigenin
liquiritigenin
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
enzyme of anthocyanin biosynthesis
-
-
-
additional information
?
-
-
light-induced increase in activity, enzyme of phenylpropanoid metabolism
-
-
-
additional information
?
-
-
enzyme is induced by trans-cinnamic acid
-
-
-
additional information
?
-
-
involved in biosynthesis of 5-hydroxyflavonoids, 5-deoxyflavonoids and retrochalcone
-
-
-
additional information
?
-
-
the enzyme catalyzes a step common to the synthesis of flavonoid pigments and isoflavonoid phytoalexins
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
elicitor, heat-released from cell walls of the phytopathogenic fungus Colletotrichum lindemuthianum, induces synthesis of both active and inactive chalcone isomerase
-
-
-
additional information
?
-
-
key enzyme in flavonoid biosynthesis
-
-
-
additional information
?
-
-
enzyme of the phenylpropanoid pathway
-
-
-
additional information
?
-
-
UV-light induced increase in activity
-
-
-
additional information
?
-
-
the enzyme is an essential compound in the biosynthesis of anthocyanin pigments, inducers of Rhizobium nodulation genes, and antimicrobial phytoalexins
-
?
additional information
?
-
Q8LKP9, -
key role of the enzyme in total flavonoid and apigenin synthesis
-
-
-
additional information
?
-
-
presence of a premature stop codon in the gold CHI gene results in an inactive chalcone isomerase. Inactivation of chalcone isomerase results in a block in the flavonoid biosynthesis pathway and the accumulation of chalcone derivatives, including a yellow pigment which might be responsible for the unusual gold color in onion
-
-
-
additional information
?
-
-, Q33DL3
the enzyme plays a major part in the cyclization reaction from chalcone to flavanone
-
-
-
additional information
?
-
A7KTI4, -
CHI is involved in the anthocyanin biosynthetic pathway
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
6'-deoxychalcone
?
show the reaction diagram
-
two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
-
?
naringenin chalcone
naringenin
show the reaction diagram
-
i.e. 6'-hydroxychalcone
-
-
?
6'-hydroxychalcone
?
show the reaction diagram
-
two isoenzymes act on both 6'-hydroxychalcone and 6'-deoxychalcone and are presumably involved in the legume-specific 6'-deoxyflavonoid pathway, while the other acts only on 6'-hydroxychalcone
-
?
additional information
?
-
-
enzyme of anthocyanin biosynthesis
-
-
-
additional information
?
-
-
light-induced increase in activity, enzyme of phenylpropanoid metabolism
-
-
-
additional information
?
-
-
enzyme is induced by trans-cinnamic acid
-
-
-
additional information
?
-
-
involved in biosynthesis of 5-hydroxyflavonoids, 5-deoxyflavonoids and retrochalcone
-
-
-
additional information
?
-
-
the enzyme catalyzes a step common to the synthesis of flavonoid pigments and isoflavonoid phytoalexins
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
the enzyme plays an important role in flavonoid metabolism
-
-
-
additional information
?
-
-
elicitor, heat-released from cell walls of the phytopathogenic fungus Colletotrichum lindemuthianum, induces synthesis of both active and inactive chalcone isomerase
-
-
-
additional information
?
-
-
key enzyme in flavonoid biosynthesis
-
-
-
additional information
?
-
-
enzyme of the phenylpropanoid pathway
-
-
-
additional information
?
-
-
UV-light induced increase in activity
-
-
-
additional information
?
-
-
the enzyme is an essential compound in the biosynthesis of anthocyanin pigments, inducers of Rhizobium nodulation genes, and antimicrobial phytoalexins
-
?
additional information
?
-
Q8LKP9, -
key role of the enzyme in total flavonoid and apigenin synthesis
-
-
-
additional information
?
-
-
presence of a premature stop codon in the gold CHI gene results in an inactive chalcone isomerase. Inactivation of chalcone isomerase results in a block in the flavonoid biosynthesis pathway and the accumulation of chalcone derivatives, including a yellow pigment which might be responsible for the unusual gold color in onion
-
-
-
additional information
?
-
-, Q33DL3
the enzyme plays a major part in the cyclization reaction from chalcone to flavanone
-
-
-
additional information
?
-
A7KTI4, -
CHI is involved in the anthocyanin biosynthetic pathway
-
-
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2',4'-Dihydroxy-4-methoxychalcone
-
substrate inhibition at 0.025 mM and above
2',4'-Dimethoxy-4-hydroxychalcone
-
inhibits isomerization of 4,2',4'-trihydroxychalcone
3,9-Dihydroxypterocarpan
-
inhibits isomerization of 4,2',4'-trihydroxychalcone
4,2',4'-trihydroxychalcone
-
substrate inhibition at 0.025 mM and above
4,2',4'-trihydroxychalcone
-
substrate inhibition
4,4'-Dihydroxychalcone
-
-
5,7,2',4'-Tetrahydroxy-8-(3,3-dimethylallyl)isoflavanone
-
i.e. kievitone, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,2',4'-Tetrahydroxyisoflavanone
-
i.e. dalbergioidin, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,2',4'-tetrahydroxyisoflavone
-
i.e. 2'-hydroxygenistein, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,3',4',5'-Pentahydroxyflavonol
-
i.e. myricetin, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,4',5'-Tetrahydroxyflavanol
-
i.e. quercetin, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,4',5'-Tetrahydroxyflavanol
-
-
5,7,4'-Trihydroxyflavanone
-
i.e. naringenin, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,4'-Trihydroxyflavanone
-
-
5,7,4'-Trihydroxyflavanone
-
competitive towards 4,2',4',6'-tetrahydroxychalcone
5,7,4'-trihydroxyflavone
-
i.e. apigenin, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,4'-trihydroxyflavonol
-
i.e. kaempferol, inhibits isomerization of 4,2',4'-trihydroxychalcone
5,7,4'-trihydroxyflavonol
-
-
5,7,4'-trihydroxyisoflavone
-
i.e. genistein, inhibits isomerization of 4,2',4'-trihydroxychalcone
6,4'-Dihydroxyaurone
-
inhibits isomerization of 4,2',4'-trihydroxychalcone
7,12-Dihydroxycoumestan
-
i.e. coumestrol, inhibits isomerization of 4,2',4'-trihydroxychalcone
7,3',4'-Trihydroxyflavonol
-
i.e. fisetin, inhibits isomerization of 4,2',4'-trihydroxychalcone
7,3'-Dihydroxy-4'-methoxyflavonol
-
inhibits isomerization of 4,2',4'-trihydroxychalcone
7,4'-Dihydroxyflavone
-
inhibits isomerization of 4,2',4'-trihydroxychalcone
7,4'-dihydroxyflavonol
-
inhibits isomerization of 4,2',4'-trihydroxychalcone
7-Hydroxy,4'-methoxyflavone
-
inhibits isomerization of 4,2',4'-trihydroxychalcone
7-Hydroxy-3',4'-dimethylchromanocoumaran
-
i.e. phaseollin, inhibits isomerization of 4,2',4'-trihydroxychalcone
diethyl dicarbonate
-
4,4'-dihydroxychalcone protects, treatment with hydroxylamine does not restore activity. In the presence of morin hydrate, all of the histidine residues of chalcone isomerase can be modified without significant loss in catalytic activity
EDTA
-
10 mM, 25% inactivation
HgCl2
-, Q43056
mutant enzyme Cys119Ala, is less sensitive than wild type enzyme
HgCl2
-
complete restoration of activity after treatment with KCN or thiols. Complete protection by 5,7,4'-trihydroxyflavanone
morin
-
competitive towards 4,2',4',6'-tetrahydroxychalcone
Morin hydrate
-
competitive
N-bromosuccinimide
-
1 mM, complete inhibition
Naringenin
-
0.01 mM, 30% inhibition
NEM
-, Q43056
mutant enzyme Cys119Ala, is less sensitive than wild type enzyme
NEM
-
10 mM, slight inactivation
p-hydroxymercuribenzoate
Soja hispida
-
-
p-hydroxymercuribenzoate
-
complete restoration of activity after treatment with KCN or thiols. Complete protection by 5,7,4'-trihydroxyflavanone
phloretin
-
0.001 mM, 36% inhibition
tetrathionate
-
-
iodoacetamide
-, Q43056
mutant enzyme Cys119Ala, is less sensitive than wild type enzyme
additional information
Soja hispida
-
no inhibition by azide, cyanide, diethyldithiocarbamate, EDTA
-
additional information
-
the activity of CHI decreases under shade
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
B2KK57, -
CHI enzymatic activity is not changed after hairy roots treated with PEG8000
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0072
-
2',4',6'-Trihydroxychalcone
-
isoenzyme II
0.0227
-
2',4'-dihydrochalcone
-
pH 7.5, 25C
0.008
-
2',4'-Dihydroxy-4-methoxychalcone
-
-
0.021
-
2',4'-dihydroxy-4-methylchalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.049
-
2',4'-dihydroxy-4-methylchalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.042
-
2',4'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.15
-
2',4'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.01
-
2'-hydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.021
-
2'-hydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.112
-
4,2',4',6'-tetrahydrochalcone
-
pH 7.5, 25C
0.002
-
4,2',4',6'-Tetrahydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.0043
-
4,2',4',6'-Tetrahydroxychalcone
-
methanethiolated enzyme
0.0063
-
4,2',4',6'-Tetrahydroxychalcone
-
native enzyme
0.007
-
4,2',4',6'-Tetrahydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.0119
-
4,2',4',6'-Tetrahydroxychalcone
-
isoenzyme II
0.0133
-
4,2',4',6'-Tetrahydroxychalcone
-
-
0.015
-
4,2',4',6'-Tetrahydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.0162
-
4,2',4',6'-Tetrahydroxychalcone
-
isoenzyme I
0.0084
-
4,2',4'-trihydrochalcone
-
pH 7.5, 25C
0.0089
-
4,2',4'-trihydroxychalcone
-
-
0.01
-
4,2',4'-trihydroxychalcone
-
-
0.018
-
4,2',4'-trihydroxychalcone
-
-
0.02
-
4,2',4'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.03
-
4,2',4'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.12
-
4,2',4'-trihydroxychalcone
-
methanethiolated enzyme
0.18
-
4,2',4'-trihydroxychalcone
-
native enzyme
0.015
-
4,2',5'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.029
-
4,2',5'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.0425
-
4,2'-dihydrochalcone
-
pH 7.5, 25C
0.013
-
4,2'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.02
-
4,2'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
0.0075
-
butein
-
-
0.0143
-
isoliquiritigenin
-
-
0.004
-
liquiritigenin
-
-
0.004
-
liquiritigenin
-
4,2',4',6'-tetrahydroxychalcone
0.043
-
Naringenin chalcone
-
-
0.004
-
liquiritigenin
-
2',4',6'-trihydroxychalcone, isoenzyme I
additional information
-
additional information
-
calculated and experimentally-derived free-energy barriers for the Michael addition of the deprotonated forms of chalcone and 6'-deoxychalcone in aqueous solution and enzyme. Substrates may exist in at least two different conformational forms according to the relative disposition of the carbonyl group and the alpha,beta-double bond. Only the S-trans conformer, which is not the most stable one in aqueous solution, is able to proceed up to the reaction products
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
45300
-
2',4'-dihydrochalcone
-
pH 7.5, 25C
35.5
-
2',4'-dihydroxy-4-methylchalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
96.8
-
2',4'-dihydroxy-4-methylchalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
42
-
2',4'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
86.3
-
2',4'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
37.4
-
2'-hydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
59.9
-
2'-hydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
670800
-
4,2',4',6'-tetrahydrochalcone
-
pH 7.5, 25C
671000
-
4,2',4',6'-tetrahydrochalcone
-
pH 7.5, 25C
1.87
-
4,2',4',6'-Tetrahydroxychalcone
-
-
152.2
-
4,2',4',6'-Tetrahydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
219.1
-
4,2',4',6'-Tetrahydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
478.8
-
4,2',4',6'-Tetrahydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
700
-
4,2',4',6'-Tetrahydroxychalcone
-
methanethiolated enzyme
833
-
4,2',4',6'-Tetrahydroxychalcone
-
native enzyme
135000
-
4,2',4'-trihydrochalcone
-
pH 7.5, 25C
51.3
-
4,2',4'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
84.5
-
4,2',4'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
107
-
4,2',4'-trihydroxychalcone
-
methanethiolated enzyme
167
-
4,2',4'-trihydroxychalcone
-
native enzyme
183
-
4,2',4'-trihydroxychalcone
-
-
32.5
-
4,2',5'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
62.5
-
4,2',5'-trihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
5526
-
4,2'-dihydrochalcone
-
pH 7.5, 25C
5530
-
4,2'-dihydrochalcone
-
pH 7.5, 25C
22.6
-
4,2'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
57.4
-
4,2'-dihydroxychalcone
Q53B70, Q53B74, Q93XE6
pH 8, 20C
48.33
-
butein
-
-
2300
-
Naringenin chalcone
-
-
38.33
-
isoliquiritigenin
-
-
additional information
-
additional information
-
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.2
-
Soja hispida
-
-
340
-
-
-
additional information
-
-
-
additional information
-
-
-
additional information
-
-
-
additional information
-
-, Q43056
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.5
6.5
-
60% of maximal activity but only 10% of the selfcyclization is observed at pH 7.5, more acurate measurement of enzyme activity than at its optimum pH 7.5
7
8.7
-
isomerization of 4,2',4'-trihydroxychalcone
7.3
7.8
Soja hispida
-
-
7.4
-
-
-
7.5
-
-
maximal activity, but enzyme activity is difficult to measure at this pH because of the spontaneous isomerization of the chalcone
7.5
-
-
assay at
8.2
-
-
4,2',4'-trihydroxychalcone
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
at pH 7.5 reactions of 4,2',4',6'-tetrahydrochalcone and 4,2',4'-trihydrochalcone and 2',4'-dihydroxychalcone are 90% diffusion controlled, whereas cyclization of 4,2'-dihydroxychalcone is limited by a chemical step that likely reflects the higher pKa of the 2'-hydroxyl group. At pH 6.0 the reactions with 4,2',4',6'-tetrahydrochalcone and 4,2',4'-trihydroxychalcone are 50% diffusion limited, whereas the reactions of 2',4'-dihydroxychalcone and 4,2'-dihydroxychalcone are limited by chemical steps
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-
assay at
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.7
-
-
calculated
7.76
-
-
sequence calulation
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
treated with fungal elicitor
Manually annotated by BRENDA team
Lupinus luteus Polo
-
embryo axes
-
Manually annotated by BRENDA team
-
embryo axes from cotyledons
Manually annotated by BRENDA team
Lupinus luteus Polo
-
embryo axes from cotyledons
-
Manually annotated by BRENDA team
Citrus unshiu Guoqing No. 4 satsuma
-
-
-
Manually annotated by BRENDA team
A2IBF8, -
preferential expression in developing fiber
Manually annotated by BRENDA team
Gossypium hirsutum T586
-
preferential expression in developing fiber
-
Manually annotated by BRENDA team
-
very low activity rapidly increases in the transcript level by wounding the cotyledons
Manually annotated by BRENDA team
-
developing
Manually annotated by BRENDA team
D6MPE5
low expression
Manually annotated by BRENDA team
C3VPI9
CHI real-time PCR expression analysis during maturation, overview
Manually annotated by BRENDA team
Citrus unshiu Guoqing No. 4 satsuma
-
CHI real-time PCR expression analysis during maturation, overview
-
Manually annotated by BRENDA team
-
infected with Colletotrichum lindemuthianum
Manually annotated by BRENDA team
-
very low activity rapidly increases in the transcript level by wounding the cotyledons
Manually annotated by BRENDA team
A9ZMJ9
low amount
Manually annotated by BRENDA team
D6MPE5
high expression
Manually annotated by BRENDA team
-
developmental expression pattern, overview
Manually annotated by BRENDA team
-
root nodule, enzyme expression is localized to the infected cells of the fixation zone
Manually annotated by BRENDA team
-
white and coloured, activity in white flowers is lower
Manually annotated by BRENDA team
Citrus unshiu Guoqing No. 4 satsuma
-
-
-
Manually annotated by BRENDA team
-
high activity in tips and young roots. Low activity in root nodules elicited by wild-type strains of Rhizobium meliloti
Manually annotated by BRENDA team
-
root nodule, enzyme expression is localized to the infected cells of the fixation zone
Manually annotated by BRENDA team
D6MPE5
highest expression
Manually annotated by BRENDA team
-
very low activity rapidly increases in the transcript level by wounding the cotyledons
Manually annotated by BRENDA team
D6MPE5
low espression
Manually annotated by BRENDA team
additional information
-
GbCHI is expressed in a tissue-specific manner
Manually annotated by BRENDA team
additional information
C3VPI9
expression of CHS and CHI genes declines gradually in peels, as well as the concentrations of total flavonoids, trans-chalcone, narirutin and hesperidin, but enzyme expression is upregulated in pulps, overview
Manually annotated by BRENDA team
additional information
Citrus unshiu Guoqing No. 4 satsuma
-
expression of CHS and CHI genes declines gradually in peels, as well as the concentrations of total flavonoids, trans-chalcone, narirutin and hesperidin, but enzyme expression is upregulated in pulps, overview
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
in embryo axes
Manually annotated by BRENDA team
Lupinus luteus Polo
-
in embryo axes
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
15600
-
-
meniscus-depletion equilibrium sedimentation
24000
-
-
gel filtration
24000
-
-
gel filtration
27200
-
-
gel filtration
30000
-
-
gel filtration
30000
-
-
gel filtration
44000
-
-
enzyme from anthers, gel filtration
62500
-
-
enzyme from limbs, gel filtration
129000
-
-
non-denaturing PAGE
130000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
x * 27000, SDS-PAGE
?
-
x * 24000, calculated
?
-
x * 26290, about, sequence calculation
monomer
-
1 * 29000, SDS-PAGE
monomer
-
1 * 24000, SDS-PAGE
monomer
-
1 * 27800, SDS-PAGE
monomer
-
1 * 28000, SDS-PAGE
monomer
-
1 * 24000, SDS-PAGE
tetramer
-
4 * 30000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
no glycoprotein
-
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
hanging-drop vapor-diffusion method
-
hanging-drop vapor-diffusion method. 1.85 A resolution crystal structure of the enzyme in complex with (2S)-naringenin reveals an open-faced beta-sandwich fold
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, 5% glycerol, 35% loss of activity after 6 weeks
-
4C, 0.129 mg enzyme per ml, 95% of the original activity is retained after 6 days
-
2C-4C, freeze-dried preparation, stable for several weeks
Soja hispida
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
recombinant enzyme
-
recombinant His-tagged CHI from Escherichia coli strain BL21 (DE3)
-
recombinant; recombinant; recombinant
Q53B70, Q53B74, Q93XE6
partial, 3 isoenzymes
-
recombinant enzyme
-, Q43056
-
Soja hispida
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
overexpressed in Escherichia coli
-
gene CHI, DNA and amino acid sequence determination and analysis, real-time quantitative PCR expression analysis
C3VPI9
expression in Arabidopsis thaliana transparent testa 5 mutant defective in naringenin production
-
gene GbCHI, DNA and amino acid sequence determination and analysis, real-time quantitative PCR expression analysis, recombinant expression of His-tagged CHI in Escherichia coli strain BL21 (DE3)
-
expression in bacteria or Saccharomyces cerevisiae; expression in bacteria or Saccharomyces cerevisiae; expression in bacteria or Saccharomyces cerevisiae
Q53B70, Q53B74, Q93XE6
expressed in hairy root cultures of Glycyrrhiza uralensis
B2KK57, -
expressed in Streptomyces venezuelae strain DHS2001
-
expression in Escherichia coli
-
isolation of cDNA
-
expressed in Escherichia coli
A7KTI4, -
expressed in Escherichia coli BL21 cells
-
coexpression with a 4-coumarate:CoA ligase and chalcone synthase in Escherichia coli for synthesis of unnatural flavonoids and stilbenes
-
overexpression in Escherichia coli
-, Q43056
expression in Escherichia coli JM109
A9ZMJ9
expression in Nicotiana tabacum
-
overexpression in Saussurea involucrata
-
combinatorial expression of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase in Saccharomyces cerevisiae
-
gene SbCHI, DNA and amino acid sequence determination and analysis, phylogenetic analysis and tree
G3CRC0, -
gene TFGCHI-1, cloning from leaves, DNA and amino acid sequence determination and analysis, phylogenetic tree, quantitative real-time PCR expression analysis, recombinant expression in Escherichia coli strains DH10B and BL21(DE3), functional complementation of CHI-deficient Arabidopsis thaliana loss-of-function mutant tt5
-
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
gene GbCHI is upregulated by UV-B irradiation or treatment with 5-aminolevulinic acid or three plant growth regulator, i.e. ethylene, abscisic acid, and chlormequat, expression analysis, and analysis of the GbCHI promoter region, overview
-
induction of gene cHI expression by Fusarium oxysporum f.sp. lupini inoculation and by increased sucrose
-
induction of gene cHI expression by Fusarium oxysporum f.sp. lupini inoculation and by increased sucrose
Lupinus luteus Polo
-
-
increase at stage of pigmetation inititation
A9ZMJ9
SbCHI is induced by treatment with wounding or methyl jasmonate
G3CRC0, -
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
expression in Arabidopsis thaliana transparent testa 5 mutant which is defective in naringenin production and therefore gives yellow seeds results in recovery of normal seed coat colour
additional information
-
production of enzyme derivatives in which the Cys residue has been converted to a series of unnatural amino acids. The results demonstrate that the Cys residue does not function as an acid-base or nucleophilic group during catalysis nor does it play any role in the substrate inhibition
C119A
-, Q43056
mutant enzyme Cys119Ala, is less sensitive to SH-inhibitors, shows chalcone isomerase activity
additional information
G3CRC0, -
SbCHI-overexpressing and SbCH-silenced transgenic hairy root lines are established by using an Agrobacterium rhizogenes-mediated system. SbCHI-overexpressing hairy root lines show enhanced SbCHI gene expression and produce more flavones, i.e. baicalin, baicalein, and wogonin, than the control hairy root line, phenotype, overview
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
analysis
-
improvements in assay procedure
synthesis
-
coexpression of enzyme with a 4-coumarate:CoA ligase and chalcone synthase in Escherichia coli for synthesis of unnatural flavonoids and stilbenes. A variety of unnatural carboxylic acids such as fluorocinnamic acid, furyl acrylic acid, thienyl acylic acid, naphthyl acrylic acid are used as substrates to give the corresponding unnatural flavanones
agriculture
-
transgenic tobacco overexpressing Saussurea medusa enzyme SmCHI produces up to fivefold more total flavonoids than wild-type, mainly due to accumulation of rutin. Transgenic tobacco treated with antisense SmCHI accumulates smaller amounts of flavonoids
synthesis
-
transgenic tobacco overexpressing Saussurea medusa enzyme SmCHI produces up to fivefold more total flavonoids than wild-type, mainly due to accumulation of rutin. Transgenic tobacco treated with antisense SmCHI accumulates smaller amounts of flavonoids
synthesis
-
combinatorial expression of 4-coumaroyl:Co A ligase, chalcone synthase, chalcone isomerase, and flavanone 3beta-hydrolase in Saccharomyces cerevisiae for production of unnatural flavanones when fed with aromatic acrylic acids