KEGG   ENZYME: 1.14.14.80Help
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
BRITE hierarchy
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)
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: 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)
SSC: 100522145 403326(CYP4A24)
CFR: 102523990
CDK: 105092933
MYD: 102774956
MNA: 107526755
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
DOSA: Os01t0854800-01(Os01g0854800) Os03t0168600-01(Os03g0168600)
ATS: 109749609(LOC109749609) 109760513(LOC109760513)
ZMA: 100191749(ms26) 100192044(cl308_1) 100273463
MNG: MNEG_6476
SPAR: SPRG_03223
 » show all
Taxonomy
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

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