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Information on EC 2.1.1.336 - norbelladine O-methyltransferase
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EC Tree
2.1.1.336 norbelladine O-methyltransferaseIUBMB Comments
The enzyme, characterized from the plants Nerine bowdenii and Narcissus pseudonarcissus (daffodil), participates in the biosynthesis of alkaloids produced by plants that belong to the Amaryllidaceae family.
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Word Map
- 2.1.1.336
- amaryllidaceae
- narcissus
- galanthamine
- pseudonarcissus
-
lycoris
- galanthus
- bulb
-
para
-
o-methylation
-
gal
- aurea
- phenol
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
laomt1, norbelladine 4'-o-methyltransferase, rbn4omt, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
N4OMT1
norbelladine 4'-O-methyltransferase
N4OMT1
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + norbelladine = S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:norbelladine O-methyltransferase
The enzyme, characterized from the plants Nerine bowdenii and Narcissus pseudonarcissus (daffodil), participates in the biosynthesis of alkaloids produced by plants that belong to the Amaryllidaceae family.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 adenosyl-L-methionine + 1,2,3,4-4H-6,7-isoquinolinediol
2 S-adenosyl-L-homocysteine + 1,2,3,4-4H-6-methoxy-7-isoquinolinol + 1,2,3,4-4H-7-methoxy-6-isoquinolinol
1,2,3,4-4H-6-methoxy-7-isoquinolinol and 1,2,3,4-4H-7-methoxy-6-isoquinolinol are produced in the ratio 10.5:1
-
-
?
2 S-adenosyl-L-methionine + (-)-epinephrine
2 S-adenosyl-L-homocysteine + 4-O-methylepinephrine + 3-O-methylepinephrine
4-O-methylepinephrine and 3-O-methylepinephrine are produced in the ratio 6.0:1
-
-
?
2 S-adenosyl-L-methionine + (-)-norepinephrine
2 S-adenosyl-L-homocysteine + 4-O-methylnorepinephrine + 3-O-methylnorepinephrine
4-O-methylnorepinephrine and 3-O-methylnorepinephrine are produced in the ratio 14.7:1
-
-
?
2 S-adenosyl-L-methionine + 3,4,5-trihydroxybenzaldehyde
2 S-adenosyl-L-homocysteine + 3,5-dihydroxy-4-methoxybenzaldehyde + 5-hydroxyvanillin
3,5-dihydroxy-4-methoxybenzaldehyde and 5-hydroxyvanillin are produced in the ratio 1:99.9
-
-
?
2 S-adenosyl-L-methionine + 3,4-dihydroxybenzaldehyde
2 S-adenosyl-L-homocysteine + vanillin + isovanillin
2 S-adenosyl-L-methionine + 3,4-dihydroxybenzylamine
2 S-adenosyl-L-homocysteine + 3-hydroxy-4-methoxybenzylamine + 4-hydroxy-3-methoxybenzylamine
3-hydroxy-4-methoxybenzylamine and 4-hydroxy-3-methoxybenzylamine are produced in the ratio 21.4:1
-
-
?
2 S-adenosyl-L-methionine + 4-bromo-catechol
2 S-adenosyl-L-homocysteine + 5-bromo-2-methoxyphenol + 4-bromo-2-methoxyphenol
5-bromo-2-methoxyphenol and 4-bromo-2-methoxyphenol are produced in the ratio 54.8:1
-
-
?
2 S-adenosyl-L-methionine + 4-fluoro-catechol
2 S-adenosyl-L-homocysteine + 5-fluoro-2-methoxyphenol + 4-fluoro-2-methoxyphenol
5-fluoro-2-methoxyphenol and 4-fluoro-2-methoxyphenol are produced in the ratio 1.5:1
-
-
?
2 S-adenosyl-L-methionine + 5-hydroxyvanillin
2 S-adenosyl-L-homocysteine + 3,4-dimethoxy-5-hydroxybenzaldehyde + 3,5-dimethoxy-4-hydroxybenzaldehyde
3,4-dimethoxy-5-hydroxybenzaldehyde and 3,5-dimethoxy-4-hydroxybenzaldehyde are produced in the ratio 1:27.9
-
-
?
2 S-adenosyl-L-methionine + caffeic acid
2 S-adenosyl-L-homocysteine + ferulic acid + isoferulic acid
2 S-adenosyl-L-methionine + dopamine
2 S-adenosyl-L-homocysteine + 4-O-methyldopamine + 3-O-methyldopamine
4-O-methyldopamine and 3-O-methyldopamine are produced in the ratio 83.8:1
-
-
?
2 S-adenosyl-L-methionine + ethyl 3,4-dihydroxybenzoate
2 S-adenosyl-L-homocysteine + ethyl 3-hydroxy-4-methoxybenzoate + ethyl 4-hydroxy-3-methoxybenzoate
ethyl 3-hydroxy-4-methoxybenzoate and ethyl 4-hydroxy-3-methoxybenzoate are produced in the ratio 1:99.9
-
-
?
2 S-adenosyl-L-methionine + higenamine
2 S-adenosyl-L-homocysteine + coclaurine + isococlaurine
coclaurine and isococlaurine are produced in the ratio 99.9:1
-
-
?
2 S-adenosyl-L-methionine + norbelladine
2 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine + 3'-O-methylnorbelladine
S-adenosyl-L-methionine + dopamine
?
-
-
-
?
S-adenosyl-L-methionine + N-methylnorbelladine
?
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
2 S-adenosyl-L-methionine + 3,4-dihydroxybenzaldehyde
2 S-adenosyl-L-homocysteine + vanillin + isovanillin
-
-
-
-
?
2 S-adenosyl-L-methionine + 3,4-dihydroxybenzaldehyde
2 S-adenosyl-L-homocysteine + vanillin + isovanillin
vanillin and isovanillin are produced in the ratio 1:10.5
-
-
?
2 S-adenosyl-L-methionine + caffeic acid
2 S-adenosyl-L-homocysteine + ferulic acid + isoferulic acid
-
-
-
-
?
2 S-adenosyl-L-methionine + caffeic acid
2 S-adenosyl-L-homocysteine + ferulic acid + isoferulic acid
ferulic acid and isoferulic acid are produced in the ratio 1:1.3
-
-
?
2 S-adenosyl-L-methionine + norbelladine
2 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine + 3'-O-methylnorbelladine
-
-
-
-
?
2 S-adenosyl-L-methionine + norbelladine
2 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine + 3'-O-methylnorbelladine
the enzyme exhibis both para- and meta-O-methylation activities toward norbelladine to give 4'- and 3'-Omethylnorbelladine
-
-
?
2 S-adenosyl-L-methionine + norbelladine
2 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine + 3'-O-methylnorbelladine
the enzyme exhibis both para- and meta-O-methylation activities toward norbelladine to give 4'- and 3'-O-methylnorbelladine. 4'-O-Methylnorbelladine and 3'-O-methylnorbelladine in the ratio of 3.5:1
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
Galanthus sp.
-
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
4'-O-methylnorbelladine is an universal precursor of all the primary Amaryllidaceae alkaloid skeletons
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
?
additional information
?
-
-
no activity with vanillin, isovanillin, o-vanillin or tyramine
-
-
-
additional information
?
-
no activity with caffeic acid, vanillin, 3,4-dihydroxybenzaldehyde, and tyramine
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 S-adenosyl-L-methionine + norbelladine
2 S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine + 3'-O-methylnorbelladine
the enzyme exhibis both para- and meta-O-methylation activities toward norbelladine to give 4'- and 3'-Omethylnorbelladine
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
Galanthus sp.
-
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
4'-O-methylnorbelladine is an universal precursor of all the primary Amaryllidaceae alkaloid skeletons
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
?
S-adenosyl-L-methionine + norbelladine
S-adenosyl-L-homocysteine + 4'-O-methylnorbelladine
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0019
N-methylnorbelladine
at pH 8.8 and 37°C
0.0285
S-adenosyl-L-methionine
at pH 8.8 and 37°C
0.251
3,4-Dihydroxybenzaldehyde
pH 9.0, 37°C, product: isovanillin
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.043
N-methylnorbelladine
at pH 8.8 and 37°C
0.075
S-adenosyl-L-methionine
at pH 8.8 and 37°C
0.0011
3,4-Dihydroxybenzaldehyde
pH 9.0, 37°C, product: isovanillin
0.00275
norbelladine
pH 9.0, 37°C, product: 3'-O-methylnorbelladine
0.0084
norbelladine
pH 9.0, 37°C, product: 4'-O-methylnorbelladine
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
21.7
N-methylnorbelladine
at pH 8.8 and 37°C
2.7
S-adenosyl-L-methionine
at pH 8.8 and 37°C
0.00438
3,4-Dihydroxybenzaldehyde
pH 9.0, 37°C, product: isovanillin
0.0069
norbelladine
pH 9.0, 37°C, product: 3'-O-methylnorbelladine
0.0285
norbelladine
pH 9.0, 37°C, product: 4'-O-methylnorbelladine
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 9.5
-
pH 6.5: about 35% of maximal activity, pH 9.3: about 90% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30 - 50
-
30°C: about 60% of maximal activity, 50°C: about 55% of maximal activity
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
gene is similarly expressed in roots, bulbs, leaves, old leaves and flowering stems
brenda
highest gene expression level is found in bulbs of both young plants and acclimated plants
brenda
gene is similarly expressed in roots, bulbs, leaves, old leaves and flowering stems
brenda
gene is similarly expressed in roots, bulbs, leaves, old leaves and flowering stems
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
the enzyme is mainly localized in cytoplasm and endosome
brenda
-
the enzyme is mainly localized in cytoplasm and endosome
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
the enzyme is involved in alkaloids biosynthesis
physiological function
-
the enzyme may play a multifunctional role, and could be the foundation for Amaryllidaceae alkaloid biosynthesis in Lycoris aurea
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). NOMT2_NARAP
239
0
27093
Swiss-Prot
other Location (Reliability: 2)
NOMT3_NARAP
239
0
27131
Swiss-Prot
other Location (Reliability: 2)
NOMT4_NARAP
239
0
27137
Swiss-Prot
other Location (Reliability: 2)
NOMT5_NARAP
239
0
27137
Swiss-Prot
other Location (Reliability: 2)
NOMT_NARAP
239
0
27156
Swiss-Prot
other Location (Reliability: 2)
NOMT_NARPS
239
0
27194
Swiss-Prot
other Location (Reliability: 2)
A0A2I0BEU9_9ASPA
293
0
33029
TrEMBL
Chloroplast (Reliability: 3)
A0A835Q1Y7_VANPL
382
0
42825
TrEMBL
other Location (Reliability: 4)
A0A2I0WMY2_9ASPA
228
0
26101
TrEMBL
other Location (Reliability: 5)
A0A6B9TNK2_9ASPA
239
0
27201
TrEMBL
other Location (Reliability: 2)
F2YP46_VANPL
296
0
33245
TrEMBL
Chloroplast (Reliability: 5)
A0A2I0V853_9ASPA
58
0
6655
TrEMBL
other Location (Reliability: 3)
A0A5P1FFU9_ASPOF
313
0
34678
TrEMBL
other Location (Reliability: 3)
A0A5C2H154_LYCRD
239
0
27183
TrEMBL
other Location (Reliability: 2)
A0A835Q125_VANPL
248
0
28122
TrEMBL
other Location (Reliability: 2)
A0A835PSX1_VANPL
276
0
30710
TrEMBL
Secretory Pathway (Reliability: 3)
A0A835Q130_VANPL
283
1
32546
TrEMBL
Secretory Pathway (Reliability: 5)
A0A835VA11_VANPL
196
0
21961
TrEMBL
other Location (Reliability: 4)
A0A835PY36_VANPL
239
0
26891
TrEMBL
other Location (Reliability: 2)
A0A2I0XJ83_9ASPA
190
0
21458
TrEMBL
other Location (Reliability: 4)
A0A2I0AG13_9ASPA
133
0
14577
TrEMBL
other Location (Reliability: 5)
A0A835RTX6_VANPL
156
0
17546
TrEMBL
Chloroplast (Reliability: 4)
A0A097PJ38_DENOF
239
0
27085
TrEMBL
other Location (Reliability: 2)
A0A835U8H5_VANPL
248
0
28054
TrEMBL
other Location (Reliability: 2)
A0A835Q467_VANPL
239
0
27025
TrEMBL
other Location (Reliability: 2)
A0A346CM52_NARTA
239
0
27137
TrEMBL
other Location (Reliability: 2)
A0A835PDI7_VANPL
239
0
26952
TrEMBL
other Location (Reliability: 2)
A0A2I0XJ65_9ASPA
187
0
20907
TrEMBL
other Location (Reliability: 5)
A0A5P1FQM7_ASPOF
85
0
9476
TrEMBL
Secretory Pathway (Reliability: 5)
A0A835PU84_VANPL
276
0
30737
TrEMBL
Secretory Pathway (Reliability: 4)
A0A835RPE2_VANPL
296
0
33224
TrEMBL
Chloroplast (Reliability: 4)
A0A4P8FB83_DENOF
239
0
27145
TrEMBL
other Location (Reliability: 2)
A0A2I0XCH4_9ASPA
255
0
28768
TrEMBL
other Location (Reliability: 2)
A0A2I0B0E4_9ASPA
262
1
29622
TrEMBL
Secretory Pathway (Reliability: 1)
A0A835U8I9_VANPL
272
0
30667
TrEMBL
other Location (Reliability: 2)
A0A835VA40_VANPL
210
0
23489
TrEMBL
Mitochondrion (Reliability: 4)
F2YP45_VANPL
248
0
27930
TrEMBL
other Location (Reliability: 4)
A0A835U6V9_VANPL
152
0
16941
TrEMBL
other Location (Reliability: 4)
A0A5P8H727_LYCRD
239
0
27100
TrEMBL
other Location (Reliability: 2)
A0A4D5YH13_9ASPA
239
0
27156
TrEMBL
other Location (Reliability: 2)
A0A835PEL7_VANPL
248
0
27957
TrEMBL
other Location (Reliability: 4)
A0A2I0WIV6_9ASPA
238
0
26905
TrEMBL
other Location (Reliability: 3)
A0A2I0XJ94_9ASPA
239
0
27050
TrEMBL
other Location (Reliability: 2)
A0A5P1FGQ1_ASPOF
196
0
21832
TrEMBL
other Location (Reliability: 3)
A0A5P1FGM9_ASPOF
245
0
27425
TrEMBL
Secretory Pathway (Reliability: 2)
A0A5P1FHP4_ASPOF
193
0
21498
TrEMBL
other Location (Reliability: 5)
A0A346TLF5_NARPA
239
0
27102
TrEMBL
other Location (Reliability: 2)
A0A835UGT0_VANPL
447
0
50507
TrEMBL
other Location (Reliability: 3)
A0A2I0XJ70_9ASPA
259
0
29287
TrEMBL
other Location (Reliability: 2)
A0A5P1FRA6_ASPOF
285
0
31413
TrEMBL
Chloroplast (Reliability: 2)
A0A2I0A7B9_9ASPA
256
0
28561
TrEMBL
other Location (Reliability: 4)
A0A835QFE6_VANPL
257
0
28783
TrEMBL
other Location (Reliability: 2)
A0A2I0A8D1_9ASPA
53
0
5663
TrEMBL
other Location (Reliability: 5)
A0A835QGY7_VANPL
263
0
29515
TrEMBL
other Location (Reliability: 3)
A0A835PWK7_VANPL
239
0
26968
TrEMBL
other Location (Reliability: 2)
A0A2I0WG85_9ASPA
285
0
31584
TrEMBL
Chloroplast (Reliability: 3)
A0A5P1FEF0_ASPOF
155
0
17107
TrEMBL
other Location (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
27000
x * 27000, calculated from amino acid sequence
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
x * 27000, calculated from amino acid sequence
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) Codon Plus RIL cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
sodium chloride, cold, polyethylene glycol, sodium nitroprusside, and methyl jasmonate treatments can significantly increase LaOMT1 transcripts
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kilgore, M.B.; Augustin, M.M.; May, G.D.; Crow, J.A.; Kutchan, T.M.
CYP96T1 of Narcissus sp. aff. pseudonarcissus catalyzes formation of the para-para' C-C phenol couple in the Amaryllidaceae alkaloids
Front. Plant Sci.
7
225
2016
Galanthus elwesii, Galanthus sp., Narcissus aff. pseudonarcissus MK-2014 (A0A077EWA5)
brenda
Kilgore, M.B.; Kutchan, T.M.
The Amaryllidaceae alkaloids: biosynthesis and methods for enzyme discovery
Phytochem. Rev.
15
317-337
2016
Lycoris aurea, Narcissus aff. pseudonarcissus MK-2014 (A0A077EWA5)
brenda
Kilgore, M.B.; Augustin, M.M.; Starks, C.M.; ONeil-Johnson, M.; May, G.D.; Crow, J.A.; Kutchan, T.M.
Cloning and characterization of a norbelladine 4-O-methyltransferase involved in the biosynthesis of the Alzheimers drug galanthamine in Narcissus sp. aff. pseudonarcissus
PLoS ONE
9
e103223
2014
Narcissus aff. pseudonarcissus MK-2014 (A0A077EWA5)
brenda
Li, W.; Qiao, C.; Pang, J.; Zhang, G.; Luo, Y.
The versatile O-methyltransferase LrOMT catalyzes multiple O-methylation reactions in amaryllidaceae alkaloids biosynthesis
Int. J. Biol. Macromol.
141
680-692
2019
Lycoris radiata (A0A5C2H154), Lycoris radiata
brenda
Sun, B.; Wang, P.; Wang, R.; Li, Y.; Xu, S.
Molecular Cloning and Characterization of a meta/para-O-Methyltransferase from Lycoris aurea
Int. J. Mol. Sci.
19
1911
2018
Lycoris aurea
brenda
Reis, A.; Magne, K.; Massot, S.; Tallini, L.R.; Scopel, M.; Bastida, J.; Ratet, P.; Zuanazzi, J.A.S.
Amaryllidaceae alkaloids identification and partial characterization of montanine production in Rhodophiala bifida plant
Sci. Rep.
9
8471
2019
Zephyranthes bifida (A0A4D5YH13), Zephyranthes bifida
brenda
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Release 2023.1 (January 2023)
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