Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001231
Secondary Accession Numbers
  • HMDB0006264
  • HMDB01231
  • HMDB06264
Metabolite Identification
Common Name27-Deoxy-5b-cyprinol
Description27-Deoxy-5b-cyprinol is an intermediate in Bile acid synthesis pathway, in a sequence of reactions catalyzed by sterol 27-hydroxylase (CYP27) in the 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 (PMID: 8496170 ). 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol 3-glucuronide, a metabolite of 27-Deoxy-5b-cyprinol, is the major bile alcohol component in serum from cerebrotendinous xanthomatosis patients (PMID: 7920441 ).
Structure
Data?1582752185
Synonyms
ValueSource
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,26-tetrolChEBI
3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestaneChEBI
5beta-Cholestane 3alpha,7alpha,12alpha,27-tetrolChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetraolChEBI
Cholestane-3,7,12,26(27)-tetrolChEBI
Cholestane-3,7,12,26-tetrolChEBI
Cholestane-3,7,12,27-tetrolChEBI
5beta-Cholestane-3alpha,7alpha,12alpha,26-tetrolKegg
(3a,5b,7a,12a)-Cholestane-3,7,12,26-tetrolGenerator
(3Α,5β,7α,12α)-cholestane-3,7,12,26-tetrolGenerator
3a,7a,12a,26-Tetrahydroxy-5b-cholestaneGenerator
3Α,7α,12α,26-tetrahydroxy-5β-cholestaneGenerator
5b-Cholestane 3a,7a,12a,27-tetrolGenerator
5Β-cholestane 3α,7α,12α,27-tetrolGenerator
5b-Cholestane-3a,7a,12a,26-tetraolGenerator
5Β-cholestane-3α,7α,12α,26-tetraolGenerator
5b-Cholestane-3a,7a,12a,26-tetrolGenerator
5Β-cholestane-3α,7α,12α,26-tetrolGenerator
(25R)-5-beta-Cholestane-3-alpha,7-alpha,12-alpha,26-tetraolHMDB
5-b-Cholestane-3a-7-tetraolHMDB
5-beta-Cholestane-3-alpha-7-alpha-12-alpha-26-tetraolHMDB
5-beta-Cholestane-3a-7-tetraolHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetraolHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27-tetrolHMDB
5beta-Cholestane-3alpha,7alpha,12alpha,27alpha-tetrolHMDB
5 beta-Cholestane-3alpha,7alpha,12alpha,26-tetrolHMDB
5-CTTLHMDB
Cholestane-3,7,12,26-tetrol, (3alpha,5alpha,7alpha,12alpha)-isomerHMDB
Chemical FormulaC27H48O4
Average Molecular Weight436.6676
Monoisotopic Molecular Weight436.355260024
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Name5-cttl
CAS Registry Number862-53-3
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO
InChI Identifier
InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyXJZGNVBLVFOSKJ-XZULNKEGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP3.77ALOGPS
logP3.62ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-0.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area80.92 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.73 m³·mol⁻¹ChemAxon
Polarizability53.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+207.16931661259
DarkChem[M-H]-198.98531661259
AllCCS[M+H]+212.00532859911
AllCCS[M-H]-205.63532859911
DeepCCS[M-2H]-242.82830932474
DeepCCS[M+Na]+216.84630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
27-Deoxy-5b-cyprinol[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO3195.1Standard polar33892256
27-Deoxy-5b-cyprinol[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO3543.9Standard non polar33892256
27-Deoxy-5b-cyprinol[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO3905.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
27-Deoxy-5b-cyprinol,1TMS,isomer #1CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3494.1Semi standard non polar33892256
27-Deoxy-5b-cyprinol,1TMS,isomer #2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3549.0Semi standard non polar33892256
27-Deoxy-5b-cyprinol,1TMS,isomer #3CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3542.2Semi standard non polar33892256
27-Deoxy-5b-cyprinol,1TMS,isomer #4CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C3545.6Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C3441.2Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C3466.8Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #3CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3444.4Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #4CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C3504.1Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #5CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O3478.4Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TMS,isomer #6CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C3500.5Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C3445.8Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C3430.8Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #3CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3450.1Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TMS,isomer #4CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C3432.2Semi standard non polar33892256
27-Deoxy-5b-cyprinol,4TMS,isomer #1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C)CO[Si](C)(C)C3445.7Semi standard non polar33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #1CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3707.1Semi standard non polar33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3759.4Semi standard non polar33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #3CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O3765.1Semi standard non polar33892256
27-Deoxy-5b-cyprinol,1TBDMS,isomer #4CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C3777.5Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C3874.7Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #2CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3908.9Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #3CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3874.5Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #4CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C3979.4Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #5CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3913.7Semi standard non polar33892256
27-Deoxy-5b-cyprinol,2TBDMS,isomer #6CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C3946.1Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C4104.0Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #2CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C4077.9Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #3CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4094.2Semi standard non polar33892256
27-Deoxy-5b-cyprinol,3TBDMS,isomer #4CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O)CO[Si](C)(C)C(C)(C)C4125.4Semi standard non polar33892256
27-Deoxy-5b-cyprinol,4TBDMS,isomer #1CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C4315.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05vx-0539800000-97d0e900e0ff8088e8ae2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2210079000-59774cc66a8ee849736f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 27-Deoxy-5b-cyprinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Positive-QTOFsplash10-0uxr-0000900000-a7bb325d6ee8da9221442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Positive-QTOFsplash10-0uxr-1004900000-c638ee962db83c052bc52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Positive-QTOFsplash10-000i-2109100000-69c195557b16f6759fe22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Negative-QTOFsplash10-00kr-0001900000-ac185007bede2c7676512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Negative-QTOFsplash10-00kr-0003900000-c665bc9fb94b91ab203e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Negative-QTOFsplash10-000i-2009400000-5648c1610aafe0315c852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Negative-QTOFsplash10-000i-0000900000-70eabfb538b202d65e502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Negative-QTOFsplash10-000i-0000900000-96d84b6ae4900e35a01e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Negative-QTOFsplash10-001i-0002900000-aedbb2b65b87f50fb9262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 10V, Positive-QTOFsplash10-0fri-0000900000-260248684581f7f3ef512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 20V, Positive-QTOFsplash10-0udi-4322900000-e31a265ff7b793fc85772021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Deoxy-5b-cyprinol 40V, Positive-QTOFsplash10-0a4i-9421000000-a3832dd065b12eca2a9a2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022502
KNApSAcK IDNot Available
Chemspider ID167758
KEGG Compound IDC05446
BioCyc IDNot Available
BiGG ID45828
Wikipedia LinkNot Available
METLIN ID6095
PubChem Compound193321
PDB IDNot Available
ChEBI ID17278
Food Biomarker OntologyNot Available
VMH IDM01092
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Holmberg-Betsholtz I, Lund E, Bjorkhem I, Wikvall K: 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. J Biol Chem. 1993 May 25;268(15):11079-85. [PubMed:8496170 ]
  2. Ohshima A, Kuramoto T, Hoshita T: Biochemical studies of inherited diseases related to abnormal cholesterol metabolism. I. High-performance liquid chromatographic analysis of bile alcohol glucuronides in cerebrotendinous xanthomatosis. Biol Pharm Bull. 1994 May;17(5):721-3. [PubMed:7920441 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
5beta-Cholestane-3alpha,7alpha,12alpha-triol + Oxygen + NADPH → 27-Deoxy-5b-cyprinol + NADP + Waterdetails
27-Deoxy-5b-cyprinol → 3a,7a,12a-Trihydroxy-5b-cholestan-26-aldetails