Entry
Name
cholestanetriol 26-monooxygenase;
5beta-cholestane-3alpha,7alpha,12alpha-triol 26-hydroxylase;
5beta-cholestane-3alpha,7alpha,12alpha-triol hydroxylase;
cholestanetriol 26-hydroxylase;
sterol 27-hydroxylase;
sterol 26-hydroxylase;
cholesterol 27-hydroxylase;
CYP27A;
CYP27A1;
cytochrome P450 27A1'
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
5beta-cholestane-3alpha,7alpha,12alpha-triol,adrenodoxin:oxygen oxidoreductase (26-hydroxylating)
Reaction(IUBMB)
5beta-cholestane-3alpha,7alpha,12alpha-triol + 6 reduced adrenodoxin + 6 H+ + 3 O2 = (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + 6 oxidized adrenodoxin + 4 H2O (overall reaction) [RN:
R11142 ];
(1a) 5beta-cholestane-3alpha,7alpha,12alpha-triol + 2 reduced adrenodoxin + 2 H+ + O2 = (25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + 2 oxidized adrenodoxin + H2O [RN:
R04807 ];
(1b) (25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol + 2 reduced adrenodoxin + 2 H+ + O2 = (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + 2 oxidized adrenodoxin + 2 H2O [RN:
R03507 ];
(1c) (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al + 2 reduced adrenodoxin + 2 H+ + O2 = (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + 2 oxidized adrenodoxin + H2O [RN:
R08761 ]
Reaction(KEGG)
Substrate
5beta-cholestane-3alpha,7alpha,12alpha-triol [CPD:
C05454 ];
reduced adrenodoxin [CPD:
C00662 ];
H+ [CPD:
C00080 ];
O2 [CPD:
C00007 ];
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol;
(25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al
Product
(25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate;
oxidized adrenodoxin [CPD:
C00667 ];
H2O [CPD:
C00001 ];
(25R)-5beta-cholestane-3alpha,7alpha,12alpha,26-tetraol;
(25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-al
Comment
This mitochondrial cytochrome P-450 enzyme requires adrenodoxin. It catalyses the first three sterol side chain oxidations in bile acid biosynthesis via the neutral (classic) pathway. Can also act on cholesterol, cholest-5-ene-3beta,7alpha-diol, 7alpha-hydroxycholest-4-en-3-one, and 5beta-cholestane-3alpha,7alpha-diol. The enzyme can also hydroxylate cholesterol at positions 24 and 25. The initial source of the electrons is NADPH, which transfers the electrons to the adrenodoxin via EC
1.18.1.6 , adrenodoxin-NADP+ reductase.
History
EC 1.14.15.15 created 1976 as EC 1.14.13.15, modified 2005, modified 2012, transferred 2016 to EC 1.14.15.15
Pathway
ec00120 Primary bile acid biosynthesis
Orthology
K00488 cholestanetriol 26-monooxygenase
Genes
DNM : 101411078 101411838 101423385
STOW : 125425853 125427460
XLA : 100381137(cyp27a1) 108702937 446987(XB984297.L)
XTR : 100145331 100496109 116407844 594905
NPR : 108783869 108783870 108783871 108783872 108783878 108783885
RTEM : 120944205 120944206 120944214
BBUF : 121007459 121007461 121008616
BGAR : 122944797 122944805 122945772
DRE : 322341(cyp27a1.4) 402831(cyp27a7) 558239(si:ch211-113j14.1) 565876(si:dkey-91i10.3) 723999(zgc:136333) 795106(cyp27a1.2)
SRX : 107705485 107706665 107714212 107723676 107725254 107741910
SANH : 107658292 107659991 107660625 107660626 107677609 107683415
SGH : 107555015 107555356 107555927 107578255 107581419 107584802 107596087
CCAR : 109064887 109072531 109088722 109088733 109088804 109096773 109113433
CAUA : 113050872 113053045 113053331 113092289 113108126 113108393 113108395 113108503
PPRM : 120461532 120461533 120466971(si:dkey-91i10.3) 120491553(si:ch211-113j14.1)
MAMB : 125270463(si:dkey-91i10.3) 125270558 125270559 125270561 125270562 125274236(si:ch211-113j14.1)
IPU : 108261037 108261972 108266301 108266489 108266490 108266491 108272717(si:ch211-113j14.1)
PHYP : 113526131 113526132 113526133 113526134 113526210 113526267 113538157
SMEO : 124380536 124382704 124383131 124383132 124383214(si:dkey-91i10.3) 124392227(si:ch211-113j14.1)
TFD : 113651034(si:ch211-113j14.1) 113654303 113654508(si:dkey-91i10.3) 113654626
AMEX : 103023980 103024291 103027002 103036363
EEE : 113567700 113577222 113586367
TRU : 101062671 101063777 101069976
LCO : 104934615 104939434 109141591
NCC : 104944399 104954736 104955625
CGOB : 115017336 115026484 115026794
ELY : 117249878(si:ch211-113j14.1) 117251494(si:dkey-91i10.3) 117251800
PLEP : 121949258(si:dkey-91i10.3) 121949317 121962951(si:ch211-113j14.1)
SLUC : 116033996(si:dkey-91i10.3) 116044772(si:ch211-113j14.1)
ECRA : 117939647(si:ch211-113j14.1) 117952801(si:dkey-91i10.3)
PFLV : 114550996 114564588
GAT : 120814973 120814975 120834098
PPUG : 119220421(si:ch211-113j14.1) 119228308 119228466(si:dkey-91i10.3)
MSAM : 119900367(si:ch211-113j14.1) 119903811 119904427(si:dkey-91i10.3)
CUD : 121506513(si:ch211-113j14.1) 121522777 121522982(si:dkey-91i10.3)
ALAT : 119015239(si:ch211-113j14.1) 119025758(si:dkey-91i10.3) 119026140
MZE : 101465003 101473743 101478374
ONL : 100691854 100693469 100705229
OAU : 116314781(si:dkey-91i10.3) 116317150(si:ch211-113j14.1) 116334070
OLA : 101156051 101160538 101175691
OML : 112154786 112155582(si:dkey-91i10.3) 112156772(si:ch211-113j14.1)
XMA : 102225514 102230910 102234678 102234938
XCO : 114140560 114147791 114147794 114148371
XHE : 116715672 116722946 116723684 116723685
PRET : 103456753 103461862 103461863 103478550
PFOR : 103134814 103138135 103154130
PLAI : 106945401 106945403 106949526 106956502
PMEI : 106916312 106919596 106926480
GAF : 122826962 122840052 122840053 122840415(si:dkey-91i10.3)
CVG : 107086204 107086205 107095844 107096820
CTUL : 119774007 119774012 119778495(si:dkey-91i10.3) 119794638(si:ch211-113j14.1)
GMU : 124861938(si:ch211-113j14.1) 124870981 124871015 124871107(si:dkey-91i10.3)
NFU : 107384645 107389662 107396451
KMR : 108238813(si:dkey-91i10.3) 108244283
ALIM : 106511198 106511262 106514257 106532599
NWH : 119419001 119419472(si:dkey-91i10.3) 119429051(si:ch211-113j14.1)
AOCE : 111562629 111568532 111571431 111574457
CSEM : 103380768 103389542
POV : 109637350 109640203 109641449
SSEN : 122765461(si:ch211-113j14.1) 122783812 122784640(si:dkey-91i10.3)
HHIP : 117755070(si:dkey-91i10.3) 117755238 117778068(si:ch211-113j14.1)
HSP : 118103627(si:ch211-113j14.1) 118120133 118120203(si:dkey-91i10.3)
LCF : 108873048 108897118 108897170
SDU : 111218457 111218691 111222696
SLAL : 111653799 111667407 111672420
XGL : 120798148(si:ch211-113j14.1) 120801357(si:dkey-91i10.3) 120801379
HCQ : 109517561 109519132 109528391
BPEC : 110165678 110166041 110171370
MALB : 109955654 109972640 109974026
BSPL : 114845813(si:ch211-113j14.1) 114846707 114846743(si:dkey-91i10.3)
SASA : 106574240 106575170 106586130 106586420 106586421
OTW : 112225125 112235263 112238608(si:dkey-91i10.3) 112253824 112266509
OMY : 110495869 110501573 110520006 110520277(si:dkey-91i10.3) 110527483
OGO : 124008274 124010863 124041765 124043781 124043995(si:dkey-91i10.3)
ONE : 115107908 115110822 115129706 115133470 115136440
SALP : 111953394 111959818 111970920 111973814
SNH : 120033627(si:ch211-113j14.1) 120050736 120058201 120058325 120058328 120064454
ELS : 105016129 105016181 105019951
AANG : 118214017(si:ch211-113j14.1) 118222144(si:dkey-91i10.3) 118222523 118223580
LOC : 102687850 102689682 102690084 102695871
PSPA : 121322499 121323017 121323418 121323529(si:dkey-91i10.3)
ARUT : 117404073 117408072 117411922 117426218
LCM : 102347924 102352926 102355859(EAF2) 102357152
CMK : 103189020(si:dkey-91i10.3)
CBR : CBG_10440 CBG_14860(Cbr-daf-9)
BMY : BM_BM2557(Bma-daf-9)
GAE : 121371591 121371592 121372413
» show all
Taxonomy
Reference
Authors
Masui T, Herman R, Staple E.
Title
The oxidation of 5-beta-cholestane-3-alpha, 7-alpha, 12-alpha, 26-tetraol to 5-beta-cholestane-3-alpha, 7-alpha, 12-alpha-triol-26-oic acid via 5-beta-cholestane-3-alpha, 7-alpha, 12-alpha-triol-26-al by rat liver.
Journal
Reference
Authors
Okuda K, Hoshita N.
Title
Oxidation of 5-beta-cholestane-3 alpha, 7 alpha, 12 alpha-triol by rat-liver mitochondria.
Journal
Reference
Authors
Wikvall K.
Title
Hydroxylations in biosynthesis of bile acids. Isolation of a cytochrome P-450 from rabbit liver mitochondria catalyzing 26-hydroxylation of C27-steroids.
Journal
J Biol Chem 259:3800-4 (1984)
Reference
Authors
Andersson S, Davis DL, Dahlback H, Jornvall H, Russell DW
Title
Cloning, structure, and expression of the mitochondrial cytochrome P-450 sterol 26-hydroxylase, a bile acid biosynthetic enzyme.
Journal
J Biol Chem 264:8222-9 (1989)
Sequence
Reference
Authors
Dahlback H, Holmberg I
Title
Oxidation of 5 beta-cholestane-3 alpha,7 alpha, 12 alpha-triol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid by cytochrome P-450(26) from rabbit liver mitochondria.
Journal
Reference
Authors
Holmberg-Betsholtz I, Lund E, Bjorkhem I, Wikvall K.
Title
Sterol 27-hydroxylase in bile acid biosynthesis. Mechanism of oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid.
Journal
J Biol Chem 268:11079-85 (1993)
Reference
Authors
Pikuleva IA, Babiker A, Waterman MR, Bjorkhem I
Title
Activities of recombinant human cytochrome P450c27 (CYP27) which produce intermediates of alternative bile acid biosynthetic pathways.
Journal
Reference
Authors
Furster C, Bergman T, Wikvall K.
Title
Biochemical characterization of a truncated form of CYP27A purified from rabbit liver mitochondria.
Journal
Reference
Authors
Pikuleva IA, Puchkaev A, Bjorkhem I
Title
Putative helix F contributes to regioselectivity of hydroxylation in mitochondrial cytochrome P450 27A1.
Journal
Sequence
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