Cytochrome P450 2A6

Details

Name
Cytochrome P450 2A6
Synonyms
  • 1,4-cineole 2-exo-monooxygenase
  • 1.14.13.-
  • Coumarin 7-hydroxylase
  • CYP2A3
  • CYPIIA6
  • Cytochrome P450 IIA3
  • Cytochrome P450(I)
Gene Name
CYP2A6
Organism
Humans
Amino acid sequence
>lcl|BSEQ0037226|Cytochrome P450 2A6
MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLNTEQMYNSLMK
ISERYGPVFTIHLGPRRVVVLCGHDAVREALVDQAEEFSGRGEQATFDWVFKGYGVVFSN
GERAKQLRRFSIATLRDFGVGKRGIEERIQEEAGFLIDALRGTGGANIDPTFFLSRTVSN
VISSIVFGDRFDYKDKEFLSLLRMMLGIFQFTSTSTGQLYEMFSSVMKHLPGPQQQAFQL
LQGLEDFIAKKVEHNQRTLDPNSPRDFIDSFLIRMQEEEKNPNTEFYLKNLVMTTLNLFI
GGTETVSTTLRYGFLLLMKHPEVEAKVHEEIDRVIGKNRQPKFEDRAKMPYMEAVIHEIQ
RFGDVIPMSLARRVKKDTKFRDFFLPKGTEVFPMLGSVLRDPSFFSNPQDFNPQHFLNEK
GQFKKSDAFVPFSIGKRNCFGEGLARMELFLFFTTVMQNFRLKSSQSPKDIDVSPKHVGF
ATIPRNYTMSFLPR
Number of residues
494
Molecular Weight
56501.005
Theoretical pI
9.69
GO Classification
Functions
arachidonic acid epoxygenase activity / coumarin 7-hydroxylase activity / enzyme binding / heme binding / iron ion binding / oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen / oxygen binding / steroid hydroxylase activity
Processes
coumarin catabolic process / coumarin metabolic process / drug metabolic process / epoxygenase P450 pathway / exogenous drug catabolic process / oxidation-reduction process / small molecule metabolic process / steroid metabolic process / xenobiotic metabolic process
Components
cytoplasm / cytoplasmic microtubule / endoplasmic reticulum membrane / intracellular membrane-bounded organelle
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Pfam Domain Function
Transmembrane Regions
Not Available
Cellular Location
Endoplasmic reticulum membrane
Gene sequence
>lcl|BSEQ0021356|Cytochrome P450 2A6 (CYP2A6)
ATGCTGGCCTCAGGGATGCTTCTGGTGGCCTTGCTGGTCTGCCTGACTGTAATGGTCTTG
ATGTCTGTTTGGCAGCAGAGGAAGAGCAAGGGGAAGCTGCCTCCGGGACCCACCCCATTG
CCCTTCATTGGAAACTACCTGCAGCTGAACACAGAGCAGATGTACAACTCCCTCATGAAG
ATCAGTGAGCGCTATGGCCCCGTGTTCACCATTCACTTGGGGCCCCGGCGGGTCGTGGTG
CTGTGTGGACATGATGCCGTCAGGGAGGCTCTGGTGGACCAGGCTGAGGAGTTCAGCGGG
CGAGGCGAGCAAGCCACCTTCGACTGGGTCTTCAAAGGCTATGGCGTGGTATTCAGCAAC
GGGGAGCGCGCCAAGCAGCTCCGGCGCTTCTCCATCGCCACCCTGCGGGACTTCGGGGTG
GGCAAGCGAGGCATCGAGGAGCGCATCCAGGAGGAGGCGGGCTTCCTCATCGACGCCCTC
CGGGGCACTGGCGGCGCCAATATCGATCCCACCTTCTTCCTGAGCCGCACAGTCTCCAAT
GTCATCAGCTCCATTGTCTTTGGGGACCGCTTTGACTATAAGGACAAAGAGTTCCTGTCA
CTGTTGCGCATGATGCTAGGAATCTTCCAGTTCACGTCAACCTCCACGGGGCAGCTCTAT
GAGATGTTCTCTTCGGTGATGAAACACCTGCCAGGACCACAGCAACAGGCCTTTCAGTTG
CTGCAAGGGCTGGAGGACTTCATAGCCAAGAAGGTGGAGCACAACCAGCGCACGCTGGAT
CCCAATTCCCCACGGGACTTCATTGACTCCTTTCTCATCCGCATGCAGGAGGAGGAGAAG
AACCCCAACACGGAGTTCTACTTGAAAAACCTGGTGATGACCACGTTGAACCTCTTCATT
GGGGGCACCGAGACCGTCAGCACCACCCTGCGCTATGGCTTCTTGCTGCTCATGAAGCAC
CCAGAGGTGGAGGCCAAGGTCCATGAGGAGATTGACAGAGTGATCGGCAAGAACCGGCAG
CCCAAGTTTGAGGACCGGGCCAAGATGCCCTACATGGAGGCAGTGATCCACGAGATCCAA
AGATTTGGAGACGTGATCCCCATGAGTTTGGCCCGCAGAGTCAAAAAGGACACCAAGTTT
CGGGATTTCTTCCTCCCTAAGGGCACCGAAGTGTACCCTATGCTGGGCTCTGTGCTGAGA
GACCCCAGTTTCTTCTCCAACCCCCAGGACTTCAATCCCCAGCACTTCCTGAATGAGAAG
GGGCAGTTTAAGAAGAGTGATGCTTTTGTGCCCTTTTCCATCGGAAAGCGGAACTGTTTC
GGAGAAGGCCTGGCCAGAATGGAGCTCTTTCTCTTCTTCACCACCGTCATGCAGAACTTC
CGCCTCAAGTCCTCCCAGTCACCTAAGGACATTGACGTGTCCCCCAAACACGTGGGCTTT
GCCACGATCCCACGAAACTACACCATGAGCTTCCTGCCCCGCTGA
Chromosome Location
19
Locus
19q13.2
External Identifiers
ResourceLink
UniProtKB IDP11509
UniProtKB Entry NameCP2A6_HUMAN
GenBank Gene IDX13897
GenAtlas IDCYP2A6
HGNC IDHGNC:2610
General References
  1. Miles JS, Bickmore W, Brook JD, McLaren AW, Meehan R, Wolf CR: Close linkage of the human cytochrome P450IIA and P450IIB gene subfamilies: implications for the assignment of substrate specificity. Nucleic Acids Res. 1989 Apr 25;17(8):2907-17. [PubMed:2726448]
  2. Yamano S, Nagata K, Yamazoe Y, Kato R, Gelboin HV, Gonzalez FJ: cDNA and deduced amino acid sequences of human P450 IIA3 (CYP2A3). Nucleic Acids Res. 1989 Jun 26;17(12):4888. [PubMed:2748347]
  3. Yamano S, Tatsuno J, Gonzalez FJ: The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry. 1990 Feb 6;29(5):1322-9. [PubMed:2322567]
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  6. Gerhard DS, Wagner L, Feingold EA, Shenmen CM, Grouse LH, Schuler G, Klein SL, Old S, Rasooly R, Good P, Guyer M, Peck AM, Derge JG, Lipman D, Collins FS, Jang W, Sherry S, Feolo M, Misquitta L, Lee E, Rotmistrovsky K, Greenhut SF, Schaefer CF, Buetow K, Bonner TI, Haussler D, Kent J, Kiekhaus M, Furey T, Brent M, Prange C, Schreiber K, Shapiro N, Bhat NK, Hopkins RF, Hsie F, Driscoll T, Soares MB, Casavant TL, Scheetz TE, Brown-stein MJ, Usdin TB, Toshiyuki S, Carninci P, Piao Y, Dudekula DB, Ko MS, Kawakami K, Suzuki Y, Sugano S, Gruber CE, Smith MR, Simmons B, Moore T, Waterman R, Johnson SL, Ruan Y, Wei CL, Mathavan S, Gunaratne PH, Wu J, Garcia AM, Hulyk SW, Fuh E, Yuan Y, Sneed A, Kowis C, Hodgson A, Muzny DM, McPherson J, Gibbs RA, Fahey J, Helton E, Ketteman M, Madan A, Rodrigues S, Sanchez A, Whiting M, Madari A, Young AC, Wetherby KD, Granite SJ, Kwong PN, Brinkley CP, Pearson RL, Bouffard GG, Blakesly RW, Green ED, Dickson MC, Rodriguez AC, Grimwood J, Schmutz J, Myers RM, Butterfield YS, Griffith M, Griffith OL, Krzywinski MI, Liao N, Morin R, Palmquist D, Petrescu AS, Skalska U, Smailus DE, Stott JM, Schnerch A, Schein JE, Jones SJ, Holt RA, Baross A, Marra MA, Clifton S, Makowski KA, Bosak S, Malek J: The status, quality, and expansion of the NIH full-length cDNA project: the Mammalian Gene Collection (MGC). Genome Res. 2004 Oct;14(10B):2121-7. [PubMed:15489334]
  7. Maurice M, Emiliani S, Dalet-Beluche I, Derancourt J, Lange R: Isolation and characterization of a cytochrome P450 of the IIA subfamily from human liver microsomes. Eur J Biochem. 1991 Sep 1;200(2):511-7. [PubMed:1889415]
  8. Yun CH, Shimada T, Guengerich FP: Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol Pharmacol. 1991 Nov;40(5):679-85. [PubMed:1944238]
  9. Kitagawa K, Kunugita N, Kitagawa M, Kawamoto T: CYP2A6*6, a novel polymorphism in cytochrome p450 2A6, has a single amino acid substitution (R128Q) that inactivates enzymatic activity. J Biol Chem. 2001 May 25;276(21):17830-5. Epub 2001 Feb 16. [PubMed:11278503]
  10. Phillips IR, Shephard EA, Ashworth A, Rabin BR: Isolation and sequence of a human cytochrome P-450 cDNA clone. Proc Natl Acad Sci U S A. 1985 Feb;82(4):983-7. [PubMed:3856261]
  11. Miyazawa M, Shindo M, Shimada T: Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes. Xenobiotica. 2001 Oct;31(10):713-23. [PubMed:11695850]
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  13. Yano JK, Hsu MH, Griffin KJ, Stout CD, Johnson EF: Structures of human microsomal cytochrome P450 2A6 complexed with coumarin and methoxsalen. Nat Struct Mol Biol. 2005 Sep;12(9):822-3. Epub 2005 Aug 7. [PubMed:16086027]
  14. Yano JK, Denton TT, Cerny MA, Zhang X, Johnson EF, Cashman JR: Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization. J Med Chem. 2006 Nov 30;49(24):6987-7001. [PubMed:17125252]
  15. DeVore NM, Smith BD, Urban MJ, Scott EE: Key residues controlling phenacetin metabolism by human cytochrome P450 2A enzymes. Drug Metab Dispos. 2008 Dec;36(12):2582-90. doi: 10.1124/dmd.108.023770. Epub 2008 Sep 8. [PubMed:18779312]
  16. Hadidi H, Zahlsen K, Idle JR, Cholerton S: A single amino acid substitution (Leu160His) in cytochrome P450 CYP2A6 causes switching from 7-hydroxylation to 3-hydroxylation of coumarin. Food Chem Toxicol. 1997 Sep;35(9):903-7. [PubMed:9409631]
  17. Oscarson M, McLellan RA, Gullsten H, Agundez JA, Benitez J, Rautio A, Raunio H, Pelkonen O, Ingelman-Sundberg M: Identification and characterisation of novel polymorphisms in the CYP2A locus: implications for nicotine metabolism. FEBS Lett. 1999 Oct 29;460(2):321-7. [PubMed:10544257]
  18. Ariyoshi N, Sawamura Y, Kamataki T: A novel single nucleotide polymorphism altering stability and activity of CYP2a6. Biochem Biophys Res Commun. 2001 Mar 2;281(3):810-4. [PubMed:11237731]
  19. Kiyotani K, Fujieda M, Yamazaki H, Shimada T, Guengerich FP, Parkinson A, Nakagawa K, Ishizaki T, Kamataki T: Twenty one novel single nucleotide polymorphisms (SNPs) of the CYP2A6 gene in Japanese and Caucasians. Drug Metab Pharmacokinet. 2002;17(5):482-7. [PubMed:15618701]
  20. Saito S, Iida A, Sekine A, Kawauchi S, Higuchi S, Ogawa C, Nakamura Y: Catalog of 680 variations among eight cytochrome p450 ( CYP) genes, nine esterase genes, and two other genes in the Japanese population. J Hum Genet. 2003;48(5):249-70. Epub 2003 Apr 29. [PubMed:12721789]
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Drug Relations

Drug Relations
DrugBank IDNameDrug groupPharmacological action?ActionsDetails
DB04665CoumarinexperimentalunknownDetails
DB00184NicotineapprovedunknownsubstrateinhibitorDetails
DB00983Formoterolapproved, investigationalunknownsubstrateDetails
DB01006Letrozoleapproved, investigationalunknownsubstrateinhibitorDetails
DB00356ChlorzoxazoneapprovedunknownsubstrateDetails
DB00553MethoxsalenapprovedunknownsubstrateinhibitorDetails
DB00752Tranylcypromineapproved, investigationalunknowninhibitorDetails
DB01011Metyraponeapproved, investigationalunknowninhibitorDetails
DB01085Pilocarpineapproved, investigationalunknowninhibitorDetails
DB01159Halothaneapproved, vet_approvedunknownsubstrateDetails
DB04977PlitidepsininvestigationalunknownDetails
DB01115NifedipineapprovedunknownsubstrateDetails
DB01037Selegilineapproved, investigational, vet_approvedunknownsubstrateDetails
DB01181IfosfamideapprovedunknownsubstrateDetails
DB00313Valproic Acidapproved, investigationalunknownsubstrateinducerDetails
DB00238NevirapineapprovedunknownsubstrateDetails
DB00568Cinnarizineapproved, investigationalunknownsubstrateDetails
DB04841FlunarizineapprovedunknownsubstrateDetails
DB00471MontelukastapprovedunknownsubstrateDetails
DB07609N,N-DIMETHYL(5-(PYRIDIN-3-YL)FURAN-2-YL)METHANAMINEexperimentalunknownDetails
DB07617N-METHYL(5-(PYRIDIN-3-YL)FURAN-2-YL)METHANAMINEexperimentalunknownDetails
DB07621(5-(PYRIDIN-3-YL)FURAN-2-YL)METHANAMINEexperimentalunknownDetails
DB076234,4'-DIPYRIDYL DISULFIDEexperimentalunknownDetails
DB00182Amphetamineapproved, illicit, investigationalunknowninhibitorDetails
DB01351Amobarbitalapproved, illicitunknowninducerDetails
DB00972AzelastineapprovedunknowninhibitorDetails
DB00921Buprenorphineapproved, illicit, investigational, vet_approvedunknowninhibitorDetails
DB01156BupropionapprovedunknownsubstrateDetails
DB00604Cisaprideapproved, investigational, withdrawnunknownsubstrateDetails
DB00636Clofibrateapproved, investigationalunknowninhibitorDetails
DB06470ClomethiazoleinvestigationalunknownsubstrateDetails
DB00257Clotrimazoleapproved, vet_approvedunknowninhibitorDetails
DB00363ClozapineapprovedunknownsubstrateDetails
DB00531Cyclophosphamideapproved, investigationalunknownsubstrateDetails
DB01151Desipramineapproved, investigationalunknowninhibitorDetails
DB01234Dexamethasoneapproved, investigational, vet_approvedunknowninducerDetails
DB00470Dronabinolapproved, illicitunknownsubstrateDetails
DB00216Eletriptanapproved, investigationalunknowninducerDetails
DB01544Flunitrazepamapproved, illicitunknownsubstrateDetails
DB00544FluorouracilapprovedunknownsubstrateDetails
DB01213Fomepizoleapproved, vet_approvedunknowninhibitorDetails
DB00951Isoniazidapproved, investigationalunknowninhibitorDetails
DB01026Ketoconazoleapproved, investigationalunknowninhibitorDetails
DB00281Lidocaineapproved, vet_approvedunknownsubstrateDetails
DB01043Memantineapproved, investigationalunknowninhibitorDetails
DB00170Menadioneapproved, nutraceuticalunknowninhibitorDetails
DB01028Methoxyfluraneapproved, investigational, vet_approvedunknownsubstrateDetails
DB01110Miconazoleapproved, investigational, vet_approvedunknowninhibitorDetails
DB06712NilvadipineinvestigationalunknowninhibitorDetails
DB00316AcetaminophenapprovedunknownsubstrateDetails
DB03783PhenacetinwithdrawnunknownsubstrateDetails
DB01435Antipyrineapproved, investigationalunknownsubstrateDetails
DB01174Phenobarbitalapproved, investigationalunknowninducerDetails
DB00396Progesteroneapproved, vet_approvedunknownsubstrateDetails
DB01045RifampicinapprovedunknowninducerDetails
DB00412Rosiglitazoneapproved, investigationalunknowninhibitorDetails
DB06739SeratrodastexperimentalunknowninhibitorDetails
DB01236Sevofluraneapproved, vet_approvedunknownsubstrateDetails
DB00675TamoxifenapprovedunknownsubstrateDetails
DB00763MethimazoleapprovedunknowninhibitorDetails
DB00495ZidovudineapprovedunknownsubstrateDetails
DB00690Flurazepamapproved, illicit, investigationalunknownsubstrateDetails
DB00755Tretinoinapproved, investigational, nutraceuticalunknownsubstrateDetails
DB01274Arformoterolapproved, investigationalunknownsubstrateDetails
DB04871LorcaserinapprovednosubstrateDetails
DB01118Amiodaroneapproved, investigationalunknowninhibitorDetails
DB00312Pentobarbitalapproved, investigational, vet_approvedunknowninducerDetails
DB06292DapagliflozinapprovednosubstrateDetails
DB09068Vortioxetineapproved, investigationalnosubstrateDetails
DB09256Tegafurapproved, investigationalyessubstrateDetails
DB09327Tegafur-uracilapproved, investigationalnosubstrateDetails
DB11586Asunaprevirapproved, investigational, withdrawnnosubstrateDetails
DB09274Artesunateapproved, investigationalunknownsubstrateDetails
DB12245Triclabendazoleapproved, investigationalunknowninhibitorDetails