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Information on EC 1.14.14.B9 - fatty acid omega2/3-hydroxyase

for references in articles please use BRENDA:EC1.14.14.B9

preliminary BRENDA-supplied EC number

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EC Tree

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.B9 fatty acid omega2/3-hydroxyase

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The enzyme appears in viruses and cellular organisms

Reaction Schemes

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(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

[reduced NADPH-hemoprotein reductase]

(4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosa-4,7,10,13,16-pentaenoate

[oxidized NADPH-hemoprotein reductase]

H2O

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

[reduced NADPH-hemoprotein reductase]

(4Z,7Z,10Z,16Z,19Z)-13,14-epoxydocosa-4,7,10,16,19-pentaenoate

[oxidized NADPH-hemoprotein reductase]

H2O

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

[reduced NADPH-hemoprotein reductase]

(4Z,7Z,13Z,16Z,19Z)-10,11-epoxydocosa-4,7,13,16,19-pentaenoate

[oxidized NADPH-hemoprotein reductase]

H2O

Synonyms

CYP4F11, CYP4F12, CYP4F8, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

CYP4F11

CYP4F12

CYP4F8

CYP4F12

CYP4F12

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + [reduced NADPH-hemoprotein reductase] + O2 = (4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosa-4,7,10,13,16-pentaenoate + [oxidized NADPH-hemoprotein reductase] + H2O

2 entries

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + [reduced NADPH-hemoprotein reductase] + O2 = (4Z,7Z,10Z,16Z,19Z)-13,14-epoxydocosa-4,7,10,16,19-pentaenoate + [oxidized NADPH-hemoprotein reductase] + H2O

2 entries

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + [reduced NADPH-hemoprotein reductase] + O2 = (4Z,7Z,13Z,16Z,19Z)-10,11-epoxydocosa-4,7,13,16,19-pentaenoate + [oxidized NADPH-hemoprotein reductase] + H2O

(1)

(2)

(3)

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SYSTEMATIC NAME

IUBMB Comments

fatty acid,[NADPH-hemoprotein reductase]:oxygen oxidoreductase omega2/3-hydroxylating

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate + [reduced NADPH-hemoprotein reductase] + O2

(4Z,7Z,10Z,13Z,16Z)-20-hydroxydocosa-4,7,10,13,16-pentaenoate + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

main product, plus minor amounts of 21-hydroxy-4,7,10,13,16-(Z)-docosapentaenoic acid, no significant formation of dihydroxycompounds

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + [reduced NADPH-hemoprotein reductase] + O2

(4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosa-4,7,10,13,16-pentaenoate + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

formation of 19,20-epoxydocosapentaenoic acid, 16,17-epoxydocosahexaenoic acid, 13,14-epoxydocosahexaenoic acid, and 10,11-epoxydocosahexaenoic acid, no significant formation of 21-hydroxy- or 22-hydroxydocosahexaenoic acid. Reaction is catalyzed by both isoforms CYP4F8 and CYP4F12

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + [reduced NADPH-hemoprotein reductase] + O2

(4Z,7Z,10Z,16Z,19Z)-13,14-epoxydocosa-4,7,10,16,19-pentaenoate + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + [reduced NADPH-hemoprotein reductase] + O2

(4Z,7Z,13Z,16Z,19Z)-10,11-epoxydocosa-4,7,13,16,19-pentaenoate + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate + [reduced NADPH-hemoprotein reductase] + O2

(7Z,10Z,13Z,16Z)-19,20-epoxydocosa-7,10,13,16-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

formation of 19,20-epoxydocosatetraenoic acid, 16,17-epoxydocosatetraenoic acid, 13,14-epoxydocosatetraenoic acid, and 10,11-epoxydocosatetraenoic acid, no formation of 21-hydroxy- or 22-hydroxydocosapentaenoic acid

(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate + [reduced NADPH-hemoprotein reductase] + O2

(7Z,10Z,13Z,19Z)-16,17-epoxydocosa-7,10,13,19-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

formation of 19,20-epoxydocosapentaenoic acid, 16,17-epoxydocosapentaenoic acid, 13,14-epoxydocosapentaenoic acid, and 10,11-epoxydocosapentaenoic acid, no formation of 21-hydroxy- or 22-hydroxydocosapentaenoic acid

(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate + [reduced NADPH-hemoprotein reductase] + O2

(7Z,13Z,16Z,19Z)-10,11-epoxydocosa-7,13,16,19-tetraenoate + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2

18-hydroxyarachidonic acid + [oxidized NADPH-hemoprotein reductase] + H2O

Homo sapiens

P98187, Q9HCS2

729095

hydroxylation at C-18

astemizole + [reduced NADPH-hemoprotein reductase] + O2

? + [oxidized NADPH-hemoprotein reductase] + H2O

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

NADPH

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.4

assay at

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

assay at

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Homo sapiens

729095

P98187, Q9HCS2

UniProt

brenda

isoform Cyp4F11

UniProt

brenda

Macaca fascicularis

isoform Cyp4F12

746558

A8CBS0

UniProt

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

liver

Macaca fascicularis

A8CBR8, A8CBS0

isoforms CYP4F2/3, CYP4F11 and CYP4F12, vary 1.3- to 4.3fold, representing 8.0, 2.7 and 0.3% of total immunoquantified CYP1-4 proteins

brenda

isoforms CYP4F2/3, CYP4F11 and CYP4F12 vary 2.4- to 9.7fold, representing 36.4, 2.4 and 9.3% of total immunoquantified CYP1-4 proteins, respectively. CYP4F is the most abundant P450 subfamily in small intestines

746558

brenda

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

brenda

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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).

A8CBR8 pBLAST

A8CBR8_MACFA

Macaca fascicularis

524

60145

TrEMBL

Show Sequence

A8CBS0 pBLAST

A8CBS0_MACFA

Macaca fascicularis

524

60077

TrEMBL

Show Sequence

P98187 pBLAST

CP4F8_HUMAN

Homo sapiens

520

59995

Swiss-Prot

Show Sequence

Q9HCS2 pBLAST

CP4FC_HUMAN

Homo sapiens

524

60309

Swiss-Prot

Show Sequence

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PROTEIN VARIANTS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

G328E

Homo sapiens

P98187, Q9HCS2

mutant oxidizes prostaglandin H2 analogs U-51605 and U-44069 as recombinant CYP4F8, but the hydroxylation of arachidonic acid is shifted from C-18 to C-19

729095

Y125F

Homo sapiens

P98187, Q9HCS2

missense mutation in substrate recognition site-1, occuring naturally in low frequency. The variant oxidizes prostaglandin H2 analogs U-51605, i.e. 9,11-diazo-prostadienoic acid, and U-44069, i.e. 9alpha,11alpha-epoxymethano-prostaglandin H2 in omega2 and omega3 position, but 4,7,10,13,16-(Z)-docosatetraenoic acid and 4,7,10,13,16-(Z)-docosapentaenoic acid are not oxidized

729095

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

expression in Escherichia coli, Saccharomyces cerevisiae

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APPLICATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

medicine

Homo sapiens

P98187, Q9HCS2

missense mutation Y125F in substrate recognition site-1 occurs naturally in low frequency. The variant oxidizes two prostaglandin H2 analogs U-51605 and U-44069, but 4,7,10,13,16-(Z)-docosatetraenoic acid and 4,7,10,13,16-(Z)-docosapentaenoic acid are not oxidized

729095

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

729095

Stark, K.; Wongsud, B.; Burman, R.; Oliw, E.H.

Oxygenation of polyunsaturated long chain fatty acids by recombinant CYP4F8 and CYP4F12 and catalytic importance of Tyr-125 and Gly-328 of CYP4F8

Arch. Biochem. Biophys.

441

174-181

2005

Homo sapiens (P98187), Homo sapiens (Q9HCS2)

16112640

brenda

746558

Uehara, S.; Murayama, N.; Nakanishi, Y.; Nakamura, C.; Hashizume, T.; Zeldin, D.C.; Yamazaki, H.; Uno, Y.

Immunochemical quantification of cynomolgus CYP2J2, CYP4A and CYP4F enzymes in liver and small intestine

Xenobiotica

124-130

2015

Macaca fascicularis (A8CBR8), Macaca fascicularis (A8CBS0)

25138712

brenda

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EXTERNAL LINKS (specific for EC-Number 1.14.14.B9)

ExplorEnz (official portal for IUBMB Enzyme Nomenclature)

Expasy Enzyme Nomenclature Database

KEGG

MetaCyc

SABIO-RK

NCBI: PubMed, Protein, Nucleotide, Structure, Gene, OMIM

Enzyme Nomenclature (alternative site)

UniProt

PDB

PROSITE Database of protein families and domains

InterPro (database of protein families, domains and functional sites)

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