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
K07422  long-chain fatty acid omega-monooxygenase
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: 113612(CYP2U1)
PTR: 471267(CYP2U1)
PPS: 100993565
GGO: 101138067
PON: 100172128(CYP2U1)
NLE: 100592267
MCC: 696076
MCF: 102136088
CSAB: 103236086
CATY: 105571408
RRO: 104670048
RBB: 108515884
TFN: 117085757
MMUR: 105872331
MMU: 100040843(Cyp4a32) 13117(Cyp4a10) 13118(Cyp4a12b) 13119(Cyp4a14) 230639(Cyp4a29) 277753(Cyp4a12a) 435802(Cyp4a30b) 666168(Cyp4a31) 71519(Cyp2u1)
RNO: 24306(Cyp4a2) 266674(Cyp4a8) 298423(Cyp4a3) 310848(Cyp2u1) 50549(Cyp4a1)
CFA: 100685915(CYP2U1) 475366(CYP4A38) 610385(CYP4A11)
EJU: 114222636
BTA: 511890(CYP4A11) 516085(CYP4A22) 535227(CYP2U1) 784417
MNA: 107538291
HAI: 109379478
AJM: 119054461
PALE: 102882745
LAV: 100658393
OAA: 100088100
GGA: 422528(CYP2U1)
MGP: 100543147
CJO: 107313257
NMEL: 110398345
APLA: 101791848
ACYG: 106038668
TGU: 100229295
LSR: 110468021
SCAN: 103826258
GFR: 102035272
FAB: 101807569
PHI: 102112226
PMAJ: 107203267
CCAE: 111928332
CCW: 104697291
ETL: 114057903
FPG: 101918289
FCH: 102050655
CLV: 102085001
EGZ: 104135501
NNI: 104021317
ACUN: 113479675
PADL: 103919544
AMJ: 102561654(CYP2U1)
PSS: 102457687
CMY: 102945537
CPIC: 101939513
ACS: 100557193
PVT: 110080450
PBI: 103065133
PMUR: 107282661
TSR: 106551326
PMUA: 114604198
GJA: 107123074
XLA: 108710146(cyp2u1.L)
XTR: 100127656(cyp2u1)
NPR: 108785422
DRE: 556280(cyp2u1)
SANH: 107683164
IPU: 108262960
PHYP: 113544242
AMEX: 103032979
EEE: 113591288
TRU: 101074959
NCC: 104953567
MZE: 101466232
ONL: 100694260
OLA: 101167098
XMA: 102234763
XCO: 114145422
PRET: 103472722
CVG: 107094618
NFU: 107375264
KMR: 108233799
ALIM: 106517064
AOCE: 111570989
CSEM: 103384096
POV: 109638308
LCF: 108888243
SDU: 111236653
SLAL: 111671167
HCQ: 109511072
BPEC: 110165350
MALB: 109955577
OTW: 112241732
ELS: 105020991
SFM: 108936644
PKI: 111852140
LCM: 102348127
CMK: 103183746
RTP: 109928317
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)
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

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