KEGG   ORTHOLOGY: K07425
Entry
K07425                      KO                                     

Name
CYP4A
Definition
long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
Pathway
ko00071  Fatty acid degradation
ko00590  Arachidonic acid metabolism
ko00830  Retinol metabolism
ko01100  Metabolic pathways
ko03320  PPAR signaling pathway
ko04270  Vascular smooth muscle contraction
ko04750  Inflammatory mediator regulation of TRP channels
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00071 Fatty acid degradation
    K07425  CYP4A; long-chain fatty acid omega-monooxygenase
   00590 Arachidonic acid metabolism
    K07425  CYP4A; long-chain fatty acid omega-monooxygenase
  09108 Metabolism of cofactors and vitamins
   00830 Retinol metabolism
    K07425  CYP4A; long-chain fatty acid omega-monooxygenase
 09150 Organismal Systems
  09152 Endocrine system
   03320 PPAR signaling pathway
    K07425  CYP4A; long-chain fatty acid omega-monooxygenase
  09153 Circulatory system
   04270 Vascular smooth muscle contraction
    K07425  CYP4A; long-chain fatty acid omega-monooxygenase
  09157 Sensory system
   04750 Inflammatory mediator regulation of TRP channels
    K07425  CYP4A; long-chain fatty acid omega-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K07425  CYP4A; long-chain fatty acid omega-monooxygenase
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
    1.14.14.80  long-chain fatty acid omega-monooxygenase
     K07425  CYP4A; long-chain fatty acid omega-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, animal type
  CYP4 family
   K07425  CYP4A; long-chain fatty acid omega-monooxygenase
Other DBs
RN: R01348 R07041 R07046 R07050 R08390
GO: 0052869
Genes
HSA: 1579(CYP4A11) 284541(CYP4A22)
PTR: 456835(CYP4A22) 739864
PPS: 100972678 100972920
GGO: 101143646 101144011
PON: 100173781
NLE: 100588910
MCC: 709461 721404
MCF: 102123589 102124651(CYP4A11)
CSAB: 103224871(CYP4A22)
RRO: 104662101
RBB: 108535621
MMU: 100040843(Cyp4a32) 13117(Cyp4a10) 13118(Cyp4a12b) 13119(Cyp4a14) 230639(Cyp4a29) 277753(Cyp4a12a) 435802(Cyp4a30b) 666168(Cyp4a31)
RNO: 24306(Cyp4a2) 266674(Cyp4a8) 298423(Cyp4a3) 50549(Cyp4a1)
NGI: 103740657
CFA: 475366(CYP4A38) 482506(CYP4A37) 610385(CYP4A11)
AML: 100470061
UMR: 103670742
UAH: 113249623
ORO: 101381707
BTA: 511890(CYP4A11) 516085(CYP4A22) 784417
SSC: 100522145 110255311 403326(CYP4A24)
CFR: 102523990
CDK: 105092933
MYD: 102774956
DRO: 112314476
RAY: 107514040
MJV: 108404957
MDO: 100023663
GRA: 105796537
GAB: 108474610
VUN: 114162834
CCAJ: 109816127
ADU: 107470679
AIP: 107623710
NTA: 107812114
NTO: 104099274
NAU: 109241958
 » show all
Reference
PMID:2766932
  Authors
Kimura S, Hanioka N, Matsunaga E, Gonzalez FJ
  Title
The rat clofibrate-inducible CYP4A gene subfamily. I. Complete intron and exon sequence of the CYP4A1 and CYP4A2 genes, unique exon organization, and identification of a conserved 19-bp upstream element.
  Journal
DNA 8:503-16 (1989)
DOI:10.1089/dna.1.1989.8.503
  Sequence
[rno:50549 24306]
Reference
PMID:7679927
  Authors
Palmer CN, Richardson TH, Griffin KJ, Hsu MH, Muerhoff AS, Clark JE, Johnson EF
  Title
Characterization of a cDNA encoding a human kidney, cytochrome P-450 4A fatty acid omega-hydroxylase and the cognate enzyme expressed in Escherichia coli.
  Journal
Biochim Biophys Acta 1172:161-6 (1993)
DOI:10.1016/0167-4781(93)90285-L
  Sequence
[hsa:1579]
Reference
  Authors
Kawashima H, Naganuma T, Kusunose E, Kono T, Yasumoto R, Sugimura K, Kishimoto T
  Title
Human fatty acid omega-hydroxylase, CYP4A11: determination of complete genomic sequence and characterization of purified recombinant protein.
  Journal
Arch Biochem Biophys 378:333-9 (2000)
DOI:10.1006/abbi.2000.1831
  Sequence
[hsa:1579 284541]
LinkDB

KEGG   ORTHOLOGY: K15401
Entry
K15401                      KO                                     

Name
CYP86A1
Definition
long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
Pathway
ko00071  Fatty acid degradation
ko00073  Cutin, suberine and wax biosynthesis
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00071 Fatty acid degradation
    K15401  CYP86A1; long-chain fatty acid omega-monooxygenase
   00073 Cutin, suberine and wax biosynthesis
    K15401  CYP86A1; long-chain fatty acid omega-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K15401  CYP86A1; long-chain fatty acid omega-monooxygenase
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
    1.14.14.80  long-chain fatty acid omega-monooxygenase
     K15401  CYP86A1; long-chain fatty acid omega-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP86 family
   K15401  CYP86A1; long-chain fatty acid omega-monooxygenase
Other DBs
RN: R01348 R09452
Genes
ATH: AT5G58860(CYP86A1)
ALY: 9298712 9319613
CRB: 17876473
CSAT: 104726463 104736111 104761986
EUS: EUTSA_v10013214mg
BRP: 103851611 103856662
BNA: 106387137 106417417 106436003
BOE: 106325857 106332387
RSZ: 108843879
THJ: 104799404 104814908
CPAP: 110810038
CIT: 102613603
TCC: 18590528
LJA: Lj0g3v0102229.1(Lj0g3v0102229.1) Lj0g3v0132879.1(Lj0g3v0132879.1)
FVE: 101294542
RCN: 112166259
PPER: 18774479
PMUM: 103320591
PAVI: 110758705
PXB: 103963213
ZJU: 107410846
CSV: 101214516
CMO: 103497092
RCU: 8276374
JCU: 105630644
JRE: 108980314
QSU: 112038977
VVI: 100243236
SLY: 101259447
SPEN: 107021848
NSY: 104215579
NTO: 104120792
NAU: 109223643
INI: 109158198
SIND: 105165168
LSV: 111893148
CCAV: 112507635
DCR: 108219920
BVG: 104899987
SOE: 110803013
NNU: 104601225
OSA: 4324825
DOSA: Os01t0854800-01(Os01g0854800)
OBR: 102717945
BDI: 100833251
ATS: 109760513(LOC109760513)
SBI: 8058930
ZMA: 100192044(cl308_1) 100273463
SITA: 101759222
PDA: 103704048
MUS: 103990198
DCT: 110104795
PEQ: 110022081
ATR: 18437877
 » show all
Reference
  Authors
Hofer R, Briesen I, Beck M, Pinot F, Schreiber L, Franke R
  Title
The Arabidopsis cytochrome P450 CYP86A1 encodes a fatty acid omega-hydroxylase involved in suberin monomer biosynthesis.
  Journal
J Exp Bot 59:2347-60 (2008)
DOI:10.1093/jxb/ern101
  Sequence
[ath:AT5G58860]
Reference
PMID:9500987
  Authors
Benveniste I, Tijet N, Adas F, Philipps G, Salaun JP, Durst F
  Title
CYP86A1 from Arabidopsis thaliana encodes a cytochrome P450-dependent fatty acid omega-hydroxylase.
  Journal
Biochem Biophys Res Commun 243:688-93 (1998)
DOI:10.1006/bbrc.1998.8156
  Sequence
[ath:AT5G58860]
LinkDB

KEGG   ORTHOLOGY: K20495
Entry
K20495                      KO                                     

Name
CYP704B1
Definition
long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
Pathway
ko00071  Fatty acid degradation
ko00073  Cutin, suberine and wax biosynthesis
ko01100  Metabolic pathways
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00071 Fatty acid degradation
    K20495  CYP704B1; long-chain fatty acid omega-monooxygenase
   00073 Cutin, suberine and wax biosynthesis
    K20495  CYP704B1; long-chain fatty acid omega-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K20495  CYP704B1; long-chain fatty acid omega-monooxygenase
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
    1.14.14.80  long-chain fatty acid omega-monooxygenase
     K20495  CYP704B1; long-chain fatty acid omega-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP704 family
   K20495  CYP704B1; long-chain fatty acid omega-monooxygenase
Other DBs
RN: R01348 R09451 R09452
Genes
ATH: AT1G69500(CYP704B1)
ALY: 9323303
CRB: 17896290
CSAT: 104701580 104750786 104788010
EUS: EUTSA_v10018405mg
BRP: 103831345
BNA: 106357195 106405268
BOE: 106299122
RSZ: 108823332
THJ: 104822043
CPAP: 110825812
CIT: 102607941
TCC: 18610369
GRA: 105764502
GAB: 108478267
DZI: 111287089
EGR: 104433440
GMX: 100787802
GSJ: 114417834
VRA: 106773103
VAR: 108347322
VUN: 114167669
CCAJ: 109807855
CAM: 101510760
LJA: Lj3g3v2576010.1(Lj3g3v2576010.1)
ADU: 107471687
AIP: 107621191
LANG: 109359423
FVE: 101301291
RCN: 112196495
PPER: 18789925
PMUM: 103321679
PAVI: 110751331
MDM: 103451801
ZJU: 107428952
CSV: 101222076
CMO: 103485770
MCHA: 111023497
CMAX: 111471352
CMOS: 111450376
CPEP: 111805183
RCU: 8281833
JCU: 105630467
MESC: 110615585
POP: 7460700
PEU: 105120833
JRE: 109009280
QSU: 112005550
VVI: 100258457
SLY: 101247053
SPEN: 107030510
SOT: 102579959
CANN: 107878194
NSY: 104210908
NTO: 104119599
NAU: 109226401
INI: 109166234
SIND: 105156526
HAN: 110923306
LSV: 111880123
CCAV: 112513833
DCR: 108197204
BVG: 104897877
SOE: 110792832
NNU: 104598197
OSA: 4331756
DOSA: Os03t0168600-01(Os03g0168600)
OBR: 102721913
BDI: 100827415
ATS: 109749609(LOC109749609)
SBI: 8082128
ZMA: 100191749(ms26)
SITA: 101775677
PDA: 103698133
EGU: 105041758
MUS: 103994761
DCT: 110095250
PEQ: 110023878
AOF: 109833859
ATR: 18422027
 » show all
Reference
  Authors
Dobritsa AA, Shrestha J, Morant M, Pinot F, Matsuno M, Swanson R, Moller BL, Preuss D
  Title
CYP704B1 is a long-chain fatty acid omega-hydroxylase essential for sporopollenin synthesis in pollen of Arabidopsis.
  Journal
Plant Physiol 151:574-89 (2009)
DOI:10.1104/pp.109.144469
  Sequence
[ath:AT1G69500]
LinkDB

KEGG   ORTHOLOGY: K22887
Entry
K22887            Tight     KO                                     

Name
CYP52M1
Definition
long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
Pathway
ko00071  Fatty acid degradation
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09103 Lipid metabolism
   00071 Fatty acid degradation
    K22887  CYP52M1; long-chain fatty acid omega-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K22887  CYP52M1; long-chain fatty acid omega-monooxygenase
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
    1.14.14.80  long-chain fatty acid omega-monooxygenase
     K22887  CYP52M1; long-chain fatty acid omega-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, fungi type
  CYP52 family
   K22887  CYP52M1; long-chain fatty acid omega-monooxygenase
Other DBs
RN: R01348
COG: COG2124
Genes
AG: ACD75398(CYP52M1)
Reference
  Authors
Huang FC, Peter A, Schwab W
  Title
Expression and characterization of CYP52 genes involved in the biosynthesis of sophorolipid and alkane metabolism from Starmerella bombicola.
  Journal
Appl Environ Microbiol 80:766-76 (2014)
DOI:10.1128/AEM.02886-13
  Sequence
Reference
  Authors
Van Bogaert IN, Holvoet K, Roelants SL, Li B, Lin YC, Van de Peer Y, Soetaert W
  Title
The biosynthetic gene cluster for sophorolipids: a biotechnological interesting biosurfactant produced by Starmerella bombicola.
  Journal
Mol Microbiol 88:501-9 (2013)
DOI:10.1111/mmi.12200
  Sequence
LinkDB

KEGG   ENZYME: 1.14.14.80
Entry
EC 1.14.14.80               Enzyme                                 

Name
long-chain fatty acid omega-monooxygenase;
CYP704B1 (gene name);
CYP52M1 (gene name);
CYP4A (gene name);
CYP86A (gene name)
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
long-chain fatty acid,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (omega-hydroxylating)
Reaction(IUBMB)
a long-chain fatty acid + [reduced NADPH---hemoprotein reductase] + O2 = an omega-hydroxy-long-chain fatty acid + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R12072]
Reaction(KEGG)
R12072 > R07041 R09451 R09452;
(other) R01348 R07046
Substrate
long-chain fatty acid [CPD:C00638];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
omega-hydroxy-long-chain fatty acid [CPD:C21886];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme thiolate) enzyme. The plant enzyme CYP704B1, which is involved in the synthesis of sporopollenin, a complex polymer found at the outer layer of spores and pollen, acts on palmitate (18:0), stearate (18:0) and oleate (18:1). The plant enzyme CYP86A1 also acts on laurate (12:0). The enzyme from the yeast Starmerella bombicola (CYP52M1) acts on C16 to C20 saturated and unsaturated fatty acids and can also hydroxylate the (omega-1) position. The mammalian enzyme CYP4A acts on laurate (12:0), myristate (14:0), palmitate (16:0), oleate (18:1), and arachidonate (20:4).
History
EC 1.14.14.80 created 2015 as EC 1.14.13.205, transferred 2018 to EC 1.14.14.80
Pathway
ec00071  Fatty acid degradation
ec00073  Cutin, suberine and wax biosynthesis
ec00590  Arachidonic acid metabolism
ec01100  Metabolic pathways
Orthology
K07425  long-chain fatty acid omega-monooxygenase
K15401  long-chain fatty acid omega-monooxygenase
K20495  long-chain fatty acid omega-monooxygenase
K22887  long-chain fatty acid omega-monooxygenase
Genes
HSA: 1579(CYP4A11) 284541(CYP4A22)
PTR: 456835(CYP4A22) 739864
PPS: 100972678 100972920
GGO: 101143646 101144011
PON: 100173781
NLE: 100588910
MCC: 709461 721404
MCF: 102123589 102124651(CYP4A11)
CSAB: 103224871(CYP4A22)
RRO: 104662101
RBB: 108535621
MMU: 100040843(Cyp4a32) 13117(Cyp4a10) 13118(Cyp4a12b) 13119(Cyp4a14) 230639(Cyp4a29) 277753(Cyp4a12a) 435802(Cyp4a30b) 666168(Cyp4a31)
RNO: 24306(Cyp4a2) 266674(Cyp4a8) 298423(Cyp4a3) 50549(Cyp4a1)
NGI: 103740657
CFA: 475366(CYP4A38) 482506(CYP4A37) 610385(CYP4A11)
AML: 100470061
UMR: 103670742
UAH: 113249623
ORO: 101381707
BTA: 511890(CYP4A11) 516085(CYP4A22) 784417
SSC: 100522145 110255311 403326(CYP4A24)
CFR: 102523990
CDK: 105092933
MYD: 102774956
DRO: 112314476
RAY: 107514040
MJV: 108404957
MDO: 100023663
ATH: AT1G69500(CYP704B1) AT5G58860(CYP86A1)
LJA: Lj0g3v0102229.1(Lj0g3v0102229.1) Lj0g3v0132879.1(Lj0g3v0132879.1) Lj3g3v2576010.1(Lj3g3v2576010.1)
PXB: 103963213
MCHA: 111023497
DOSA: Os01t0854800-01(Os01g0854800) Os03t0168600-01(Os03g0168600)
ATS: 109749609(LOC109749609) 109760513(LOC109760513)
ZMA: 100191749(ms26) 100192044(cl308_1) 100273463
 » show all
Reference
1  [PMID:9500987]
  Authors
Benveniste I, Tijet N, Adas F, Philipps G, Salaun JP, Durst F
  Title
CYP86A1 from Arabidopsis thaliana encodes a cytochrome P450-dependent fatty acid  omega-hydroxylase.
  Journal
Biochem Biophys Res Commun 243:688-93 (1998)
DOI:10.1006/bbrc.1998.8156
  Sequence
[ath:AT5G58860]
Reference
2  [PMID:10620324]
  Authors
Hoch U, Zhang Z, Kroetz DL, Ortiz de Montellano PR
  Title
Structural determination of the substrate specificities and regioselectivities of the rat and human fatty acid omega-hydroxylases.
  Journal
Arch Biochem Biophys 373:63-71 (2000)
DOI:10.1006/abbi.1999.1504
Reference
3  [PMID:19700560]
  Authors
Dobritsa AA, Shrestha J, Morant M, Pinot F, Matsuno M, Swanson R, Moller BL, Preuss D
  Title
CYP704B1 is a long-chain fatty acid omega-hydroxylase essential for sporopollenin synthesis in pollen of Arabidopsis.
  Journal
Plant Physiol 151:574-89 (2009)
DOI:10.1104/pp.109.144469
  Sequence
[ath:AT1G69500]
Reference
4  [PMID:24242247]
  Authors
Huang FC, Peter A, Schwab W
  Title
Expression and characterization of CYP52 genes involved in the biosynthesis of sophorolipid and alkane metabolism from Starmerella bombicola.
  Journal
Appl Environ Microbiol 80:766-76 (2014)
DOI:10.1128/AEM.02886-13
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.80
IUBMB Enzyme Nomenclature: 1.14.14.80
ExPASy - ENZYME nomenclature database: 1.14.14.80
BRENDA, the Enzyme Database: 1.14.14.80
LinkDB

KEGG   REACTION: R01348
Entry
R01348                      Reaction                               

Name
Fatty acid,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (omega-hydroxylating)
Definition
Fatty acid + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> omega-Hydroxy fatty acid + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Enzyme
Pathway
rn00071  Fatty acid degradation
Orthology
K07425  long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
K15401  long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
K20495  long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
K22887  long-chain fatty acid omega-monooxygenase [EC:1.14.14.80]
LinkDB

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