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Information on EC 1.14.14.79 - docosahexaenoic acid omega-hydroxylase and Organism(s) Homo sapiens and UniProt Accession Q6ZWL3

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IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein isolated from human eye tissue. Defects in the enzyme are associated with Bietti crystalline corneoretinal dystrophy. The enzyme also produces some 21-hydroxydocosahexaenoate. Acts in a similar way on icosapentaenoic acid.
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This record set is specific for:
Homo sapiens
UNIPROT: Q6ZWL3
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Word Map
  • 1.14.14.79
  • dystrophy
  • bietty
  • retinal
  • corneoretinal
  • fundus
  • acuity
  • chorioretinal
  • electroretinography
  • limbus
  • full-field
  • intraretinal
  • hyperreflective
  • glittering
  • serpinc1
  • perimetry
  • crystalline-like
  • choriocapillaris
  • crystal-like
  • cyp4z1
The taxonomic range for the selected organisms is: Homo sapiens
The enzyme appears in selected viruses and cellular organisms
Synonyms
cyp4v2, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
docosahexaenoic acid omega-hydroxylase
-
SYSTEMATIC NAME
IUBMB Comments
docosahexaenoate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (22-hydroxydocosahexaenoate forming)
A cytochrome P-450 (heme-thiolate) protein isolated from human eye tissue. Defects in the enzyme are associated with Bietti crystalline corneoretinal dystrophy. The enzyme also produces some 21-hydroxydocosahexaenoate. Acts in a similar way on icosapentaenoic acid.
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
(5Z,8Z,11Z,14Z,17Z)-20-hydroxyicosa-5,8,11,14,17-pentaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
icosapentaenoate i.e. (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
-
-
?
docosahexaenoate + NADPH + H+ + O2
22-hydroxydocosahexaenoate + NADP+ + H2O
show the reaction diagram
9(10)-epoxystearic acid + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxy-9(10)-epoxystearic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
docosahexaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
22-hydroxydocosahexaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
docosapentaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
22-hydroxydocosapentaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
eicosapentaenoic acid + NADPH + H+ + O2
20-hydroxyeicosapentaenoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
?
eicosatrienoic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyeicosatrienoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
docosahexaenoate + NADPH + H+ + O2
22-hydroxydocosahexaenoate + NADP+ + H2O
show the reaction diagram
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
CYP4V2 displays a typical reduced carbon monoxide-bound P450 spectrum
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
docosahexaenoic acid
eicosapentaenoic acid
eicosatrienoic acid
10 microM, 32% inhibition of arachidonic acid metabolism
omega-3 docosapentaenoic acid
inhibitory to reaction of arachidonic acid
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
a human cell line spontaneously generated from normal human retinal pigmented epithelium
Manually annotated by BRENDA team
endothelial cell
Manually annotated by BRENDA team
islet cells
Manually annotated by BRENDA team
glandular epithelial cells
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
defects in the enzyme are associated with Bietti crystalline corneoretinal dystrophy
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
CP4V2_HUMAN
525
1
60724
Swiss-Prot
Secretory Pathway (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60000
x * 60000, SDS-PAGE
62163
x * 62163, liquid chromatography-mass spectrometry analysis
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H331P
the naturally occuring mutant protein CYP4V2 protein is expressed at high levels in ocular target tissues of patients with Bietti’s crystalline corneoretinal dystrophy. The enzyme is metabolically active toward polyunsaturated fatty acids. The functional deficit among patients with Bietti’s crystalline corneoretinal dystrophy who carry the H331P variant is most likely a consequence of the instability of the mutant protein
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
isolated through nickel affinity and hydroxyapatite chromatography
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in insect cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
expression is associated with differentiation of HepaRG cels and unaffected by fatty acid overload
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Fer, M.; Corcos, L.; Dreano, Y.; Plee-Gautier, E.; Salan, J.; Berthou, F.; Amet, Y.
Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism
J. Lipid Res.
49
2379-2389
2008
Homo sapiens (Q08477)
Manually annotated by BRENDA team
Nakano, M.; Kelly, E.J.; Wiek, C.; Hanenberg, H.; Rettie, A.E.
CYP4V2 in Biettis crystalline dystrophy: ocular localization, metabolism of omega-3-polyunsaturated fatty acids, and functional deficit of the p.H331P variant
Mol. Pharmacol.
82
679-686
2012
Homo sapiens (Q6ZWL3), Homo sapiens
Manually annotated by BRENDA team
Madec, S.; Cerec, V.; Plee-Gautier, E.; Antoun, J.; Glaise, D.; Salaun, J.P.; Guguen-Guillouzo, C.; Corlu, A.
CYP4F3B expression is associated with differentiation of HepaRG human hepatocytes and unaffected by fatty acid overload
Drug Metab. Dispos.
39
1987-1996
2011
Homo sapiens (Q08477)
Manually annotated by BRENDA team
Harmon, S.D.; Fang, X.; Kaduce, T.L.; Hu, S.; Raj Gopal, V.; Falck, J.R.; Spector, A.A.
Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production
Prostaglandins Leukot. Essent. Fatty Acids
75
169-177
2006
Homo sapiens (Q08477)
Manually annotated by BRENDA team