KEGG   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: 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
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
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

KEGG   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
PANPODANSg8563
PBELQC761_207340
PPSDQC762_207340
PPSPQC763_207340
PPSAQC764_207340
ANIANIA_07818
AORAO090026000021
AFVAFLA_006296
APUUAPUU_20044A
CBETCB0940_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

KEGG   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
Reaction class
RC01710  C20499_C20500
Enzyme
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

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