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Information on EC 2.3.1.302 - hydroxycinnamoyl-CoA:5-hydroxyanthranilate N-hydroxycinnamoyltransferase
for references in articles please use BRENDA:EC2.3.1.302
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EC Tree 2 Transferases
2.3 Acyltransferases
2.3.1 Transferring groups other than aminoacyl groups
2.3.1.302 hydroxycinnamoyl-CoA:5-hydroxyanthranilate N-hydroxycinnamoyltransferase
IUBMB Comments
The enzyme participates in the biosynthesis of avenanthramides, phenolic alkaloids found mainly in oats (Avena sativa). It is related to EC 2.3.1.133, shikimate O-hydroxycinnamoyltransferase. The enzyme from oat does not accept feruloyl-CoA as a substrate.
The enzyme appears in viruses and cellular organisms
- 2.3.1.302
-
hydroxycinnamic
-
hydroxycinnamoyl-coas
-
brassinosteroids
-
p-coumaric
-
feruloylation
- quinate
-
p-coumaroylation
-
saccharification
-
o-hydroxycinnamoyltransferase
- deacetylvindoline
-
tropane
-
coniferyl
- cutin
-
sinapoylated
- analysis
Reaction Schemes
showSynonyms
bahd acyltransferase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
BAHD acyltransferase
HHT1
HHT4
HHT1
-
-
-
-
HHT4
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(E)-4-coumaroyl-CoA + 5-hydroxyanthranilate = avenanthramide A + CoA
(1)
-
-
-
(E)-caffeoyl-CoA + 5-hydroxyanthranilate = avenanthramide C + CoA
(2)
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
avenanthramide biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
hydroxycinnamoyl-CoA:5-hydroxyanthranilate N-hydroxycinnamoyltransferase
The enzyme participates in the biosynthesis of avenanthramides, phenolic alkaloids found mainly in oats (Avena sativa). It is related to EC 2.3.1.133, shikimate O-hydroxycinnamoyltransferase. The enzyme from oat does not accept feruloyl-CoA as a substrate.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-hydroxybenzoyl-CoA + 5-hydroxyanthranilate
N-(4'-hydroxybenzoyl)-5-hydroxyanthranilic acid + CoA
-
Substrates: -
Products: -
Products: -
?
caffeoyl-CoA + L-3,4-dihydroxyphenylalanine
? + CoA
Substrates: -
Products: -
Products: -
?
cinnamoyl-CoA + 5-hydroxyanthranilate
N-cinnamoyl-5-hydroxyanthranilic acid + CoA
-
Substrates: -
Products: -
Products: -
?
feruloyl-CoA + L-phenylalanine
? + CoA
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + L-tyrosine
? + CoA
Substrates: -
Products: -
Products: -
?
avenalumoyl-CoA + 5-hydroxyanthranilate
avenanthramide L + CoA
-
Substrates: -
Products: -
Products: -
?
avenalumoyl-CoA + 5-hydroxyanthranilate
avenanthramide L + CoA
Substrates: -
Products: -
Products: -
?
caffeoyl-CoA + 5-hydroxyanthranilate
avenanthramide C + CoA
-
Substrates: -
Products: -
Products: -
?
caffeoyl-CoA + 5-hydroxyanthranilate
avenanthramide C + CoA
Substrates: -
Products: -
Products: -
?
feruloyl-CoA + 5-hydroxyanthranilate
avenanthramide B + CoA
-
Substrates: -
Products: -
Products: -
?
feruloyl-CoA + 5-hydroxyanthranilate
avenanthramide B + CoA
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + 4-hydroxyanthranilate
avenanthramide G + CoA
-
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + 4-hydroxyanthranilate
avenanthramide G + CoA
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + 5-hydroxyanthranilate
avenanthramide A + CoA
-
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + 5-hydroxyanthranilate
avenanthramide A + CoA
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + 5-hydroxyanthranilate
avenanthramide A + CoA
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + anthranilate
avenanthramide D + CoA
Substrates: -
Products: -
Products: -
?
p-coumaroyl-CoA + anthranilate
avenanthramide D + CoA
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: no substrate: feruloyl-CoA
Products: -
Products: -
?
additional information
?
-
Substrates: no substrate: feruloyl-CoA
Products: -
Products: -
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Dwarfism
Overexpression of a putative Arabidopsis BAHD acyltransferase causes dwarfism that can be rescued by brassinosteroid.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
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
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
oat HHTs are responsible for the biosynthesis of avenanthramide A and avenanthramide C using hydroxyanthranilic acid as an acyl acceptor and p-coumaroyl-CoA and caffeoyl-CoA as an acyl donor, respectively. Contrary, avenanthramide B is synthesized by a caffeoyl-CoA O-methyltransferase enzyme through the methylation of avenanthramide C
physiological function
overview on BAHD acyltransferases superfamily, conserved motifs and mechanism. HHT1 and HCBT (hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/benzoyltransferase) both produce anthramide phytoalexins, these two and agmatine coumaroyltransferase (ACT) are the enzymes that have been shown to acylate a nitrogen to form the corresponding amide
physiological function
BAHD-acyltransferases, named after the first four biochemically characterized enzymes of the group, use acyl-CoA thioesters as donor molecules, whereas SCPL (Serine CarboxyPeptidase Like)-acyltransferases use 1-O-beta-glucose esters. Review on both groups and specification of subgroups
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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). HHT4_AVESA
445
0
48217
Swiss-Prot
other Location (Reliability: 1)
A0A3B6B2J6_WHEAT
442
0
48317
TrEMBL
Secretory Pathway (Reliability: 1)
A0A3B6DF92_WHEAT
438
0
47863
TrEMBL
other Location (Reliability: 1)
A0A3B6QF84_WHEAT
442
0
48194
TrEMBL
other Location (Reliability: 4)
A0A452XKX3_AEGTS
441
0
48997
TrEMBL
Mitochondrion (Reliability: 4)
A0A452XL27_AEGTS
440
0
48866
TrEMBL
-
A0A453B6V2_AEGTS
474
0
51503
TrEMBL
-
A0A453B760_AEGTS
447
0
48429
TrEMBL
-
A0A453B765_AEGTS
476
0
51577
TrEMBL
-
A0A453B6V7_AEGTS
452
0
48922
TrEMBL
-
A0A453CBL8_AEGTS
489
0
53350
TrEMBL
-
A0A453CC06_AEGTS
438
0
47863
TrEMBL
Mitochondrion (Reliability: 2)
A0A453GUT3_AEGTS
440
0
48869
TrEMBL
-
A0A453P2L0_AEGTS
442
0
48194
TrEMBL
-
A0A453QZG2_AEGTS
466
0
50010
TrEMBL
-
A0A8I6WVV1_HORVV
438
0
47893
TrEMBL
-
A0A8I6X5J5_HORVV
447
0
48330
TrEMBL
-
A0A9R1B5L3_TRITD
439
0
48759
TrEMBL
-
A0A9R1DY94_WHEAT
427
0
46234
TrEMBL
Mitochondrion (Reliability: 3)
A0A9R1G4A6_WHEAT
442
0
48871
TrEMBL
Mitochondrion (Reliability: 4)
A0A9R1NP76_TRITD
447
0
48439
TrEMBL
Secretory Pathway (Reliability: 3)
A0A9R1NZ75_TRITD
442
0
48360
TrEMBL
other Location (Reliability: 4)
A0A9R1PUB5_TRITD
438
0
47851
TrEMBL
-
A0A9R1RVI9_TRITD
436
0
48161
TrEMBL
-
A0AAD8RJ72_LOLMU
445
0
48082
TrEMBL
Secretory Pathway (Reliability: 1)
F2DKX9_HORVV
438
0
47837
TrEMBL
other Location (Reliability: 3)
F2D7A9_HORVV
447
0
48429
TrEMBL
Secretory Pathway (Reliability: 2)
I1IZB2_BRADI
443
0
48469
TrEMBL
other Location (Reliability: 1)
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression of HHT1 and S-adenosyl-L-methionine:trans-caffeoyl-CoA 3-O-methyltransferase CCoAOMT transcripts increases concomitantly with phytoalexin accumulation by the treatment of victorin
victorin C, a host-specific toxin produced by Helminthosporium victoriae, induces hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyltransferase activity in oat leaves
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
analysis
method to measure hydroxycinnamoyl-CoA:5-hydroxyanthranilate N-hydroxycinnamoyltransferase reaction rates in real time using 5,5'-dithio-bis-(2-nitrobenzoic acid) (i.e. DTNB) to spectrophotometrically quantify, in real time, the release of free CoA during the transferase reaction
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Yang, Q.; Trinh, H.X.; Imai, S.; Ishihara, A.; Zhang, L.; Nakayashiki, H.; Tosa, Y.; Mayama, S.
Analysis of the involvement of hydroxyanthranilate hydroxycinnamoyltransferase and caffeoyl-CoA 3-O-methyltransferase in phytoalexin biosynthesis in oat
Mol. Plant Microbe Interact.
17
81-89
2004
Avena sativa (Q7XXP3)
brenda
D'Auria, J.
Acyltransferases in plants a good time to be BAHD
Curr. Opin. Plant Biol.
9
331-340
2006
Avena sativa (Q7XXP3)
brenda
Li, Z.; Chen, Y.; Meesapyodsuk, D.; Qiu, X.
The biosynthetic pathway of major avenanthramides in oat
Metabolites
9
163
2019
Avena sativa (Q7XXP3), Avena sativa (A0A4Y5UJ70)
brenda
Bontpart, T.; Cheynier, V.; Ageorges, A.; Terrier, N.
BAHD or SCPL acyltransferase? What a dilemma for acylation in the world of plant phenolic compounds
New Phytol.
208
695-707
2015
Avena sativa (Q7XXP3)
brenda
Sullivan, M.; Bonawitz, N.
Spectrophotometric determination of reaction rates and kinetic parameters of a BAHD acyltransferase using DTNB (5,5'-dithio-bis-[2-nitrobenzoic acid])
Plant Sci.
269
148-152
2018
Trifolium pratense (A0A384ZRD3)
brenda
Ishihara, A.; Matsukawa, T.; Miyagawa, H.; Ueno, T.; Iwamura, H.; Mayama, S.; Ishihara, A.; Matsukawa, T.; Miyagawa, H.; Iwamura, H.
Induction of hydroxycinnamoyl-CoA hydroxyanthranilate N-hydroxycinnamoyl-transferase (HHT) activity in oat leaves by victorin C
Z. Naturforsch. C
52
756-760
1997
Avena sativa
-
brenda
EXTERNAL LINKS (specific for EC-Number 2.3.1.302)
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