KEGG ORTHOLOGY: K17645

ORTHOLOGY: K17645

Entry

K17645                      KO

Symbol

AVNA, CYP60A1

Name

averantin hydroxylase [EC:1.14.14.116]

Pathway

map00254

Aflatoxin biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00937

Aflatoxin biosynthesis, malonyl-CoA => aflatoxin B1

Reaction

R10317

(1'S)-averantin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (5'-hydroxylating)

R10318

(1'S)-averantin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (5'-hydroxylating)

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00254 Aflatoxin biosynthesis
    K17645  AVNA, CYP60A1; averantin hydroxylase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K17645  AVNA, CYP60A1; averantin hydroxylase
Enzymes [BR:ko01000]
1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.116  averantin hydroxylase
     K17645  AVNA, CYP60A1; averantin hydroxylase
Cytochrome P450 [BR:ko00199]
Cytochrome P450, fungi type
  CYP60 family
   K17645  AVNA, CYP60A1; averantin hydroxylase

Other DBs

COG:

COG2124

GO:

0140395

Genes

PAN:	PODANSg8563

PBEL:

PPSD:

PPSP:

PPSA:

ANI:	ANIA_07818

AOR:	AO090026000021

AFV:	AFLA_006296

APUU:

APUU_20044A

CBET:

CB0940_03003

Reference

PMID:7793957

Authors

Yu J, Chang PK, Cary JW, Wright M, Bhatnagar D, Cleveland TE, Payne GA, Linz JE

Title

Comparative mapping of aflatoxin pathway gene clusters in Aspergillus parasiticus and Aspergillus flavus.

Journal

Appl Environ Microbiol 61:2365-71 (1995)
DOI:10.1128/AEM.61.6.2365-2371.1995

Sequence

[afv:AFLA_006296]

Reference

PMID:8368836

Authors

Yabe K, Matsuyama Y, Ando Y, Nakajima H, Hamasaki T

Title

Stereochemistry during aflatoxin biosynthesis: conversion of norsolorinic acid to averufin.

Journal

Appl Environ Microbiol 59:2486-92 (1993)
DOI:10.1128/AEM.59.8.2486-2492.1993

LinkDB

ENZYME: 1.14.14.116

Entry

EC 1.14.14.116              Enzyme

Name

averantin hydroxylase;
AVN hydroxylase;
avnA (gene name);
CYP60A1

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

Sysname

(1'S)-averantin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (5'-hydroxylating)

Reaction(IUBMB)

(1) (1'S)-averantin + [reduced NADPH---hemoprotein reductase] + O2 = (1'S,5'S)-5'-hydroxyaverantin + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10317];
(2) (1'S)-averantin + [reduced NADPH---hemoprotein reductase] + O2 = (1'S,5'R)-5'-hydroxyaverantin + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R10318]

Reaction(KEGG)

R10317 R10318

Substrate

(1'S)-averantin [CPD:C20499];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]

Product

(1'S,5'S)-5'-hydroxyaverantin [CPD:C20500];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
(1'S,5'R)-5'-hydroxyaverantin [CPD:C20501]

Comment

A cytochrome P-450 (heme-thiolate) protein isolated from the saprophytic mold Aspergillus parasiticus. Involved in aflatoxin biosynthesis. Does not react with (1'R)-averantin.

History

EC 1.14.14.116 created 2013 as EC 1.14.13.174, transferred 2018 to EC 1.14.14.116

Pathway

ec00254

Aflatoxin biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K17645

averantin hydroxylase

Genes

PAN:	PODANSg8563

PBEL:

QC761_207340

PPSD:

QC762_207340

PPSP:

QC763_207340

PPSA:

QC764_207340

ANI:	ANIA_07818

AOR:	AO090026000021

AFV:	AFLA_006296

APUU:

APUU_20044A

CBET:

CB0940_03003

Reference

1 [PMID:8368836]

Authors

Yabe K, Matsuyama Y, Ando Y, Nakajima H, Hamasaki T

Title

Stereochemistry during aflatoxin biosynthesis: conversion of norsolorinic acid to averufin.

Journal

Appl Environ Microbiol 59:2486-92 (1993)
DOI:10.1128/AEM.59.8.2486-2492.1993

Reference

2 [PMID:9097431]

Authors

Yu J, Chang PK, Cary JW, Bhatnagar D, Cleveland TE

Title

avnA, a gene encoding a cytochrome P-450 monooxygenase, is involved in the conversion of averantin to averufin in aflatoxin biosynthesis in Aspergillus parasiticus.

Journal

Appl Environ Microbiol 63:1349-56 (1997)
DOI:10.1128/AEM.63.4.1349-1356.1997

Other DBs

ExplorEnz - The Enzyme Database:

1.14.14.116

IUBMB Enzyme Nomenclature:

1.14.14.116

ExPASy - ENZYME nomenclature database:

1.14.14.116

BRENDA, the Enzyme Database:

1.14.14.116

LinkDB

REACTION: R10317

Entry

R10317                      Reaction

Name

(1'S)-averantin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (5'-hydroxylating)

Definition

(1'S)-Averantin + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (1'S,5'S)-5'-Hydroxyaverantin + [Oxidized NADPH---hemoprotein reductase] + H2O

Equation

C20499 + C03024 + C00007 <=> C20500 + C03161 + C00001

Reaction class

RC01710

C20499_C20500

Enzyme

1.14.14.116

Pathway

rn00254

Aflatoxin biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00937

Aflatoxin biosynthesis, malonyl-CoA => aflatoxin B1

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.116
     R10317  (1'S)-Averantin + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (1'S,5'S)-5'-Hydroxyaverantin + [Oxidized NADPH---hemoprotein reductase] + H2O

Orthology

K17645

averantin hydroxylase [EC:1.14.14.116]

Other DBs

RHEA:

35574

LinkDB

DBGET integrated database retrieval system