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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:05 UTC
HMDB IDHMDB0001457
Secondary Accession Numbers
  • HMDB01457
Metabolite Identification
Common Name5beta-Cholestane-3alpha,7alpha,12alpha-triol
Description5beta-Cholestane-3alpha,7alpha,12alpha-triol is an intermediate in bile acid biosynthesis. 5beta-Cholestane-3alpha,7alpha,12alpha-triol is the second to last step in the synthesis of 5beta-cyprinolsulfate. It is converted from 7alpha,12alpha-dihydroxy-5beta-cholestan-3-one via enzymatic reaction, and then it is converted into 3alpha,7alpha,12alpha,26-tetrahydroxy-5beta-cholestane via the enzyme cytochrome P450 (EC 1.14.13.15). This compound inhibits la-hydroxylation (PMID: 7937829 ). It is the byproduct of cholestanetetraol 26-dehydrogenase (EC 1.1.1.161) and the reaction that catalyzes it is classified as a small molecule reaction (BioCyc).
Structure
Data?1582752203
Synonyms
ValueSource
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestaneChEBI
3alpha,7alpha,12alpha-TrihydroxycoprostaneChEBI
3a,7a,12a-Trihydroxy-5b-cholestaneGenerator
3Α,7α,12α-trihydroxy-5β-cholestaneGenerator
3a,7a,12a-TrihydroxycoprostaneGenerator
3Α,7α,12α-trihydroxycoprostaneGenerator
5b-Cholestane-3a,7a,12a-triolGenerator
5Β-cholestane-3α,7α,12α-triolGenerator
5-beta-Cholestane-3-alpha,7-alpha,12-alpha-triolHMDB
3,7,12-TrihydroxycholestaneMeSH, HMDB
3,7,12-TrihydroxycoprostaneMeSH, HMDB
3,7,12-Trihydroxycoprostane, (3alpha,5alpha,7alpha,12alpha)-isomerMeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5alpha,7alpha,12alpha)-isomerMeSH, HMDB
3,7,12-Trihydroxycoprostane, (3beta,5beta,7alpha,12alpha)-isomerMeSH, HMDB
3alpha, 7alpha,12alpha-Trihydroxy-5beta-cholestaneMeSH, HMDB
5 beta-Cholestane-3 alpha,7 alpha,12 alpha-triolMeSH, HMDB
5beta-Cholestane-3alpha,7alpha,12alpha-triolMeSH, KEGG
ChtriolMeSH, HMDB
TrihydroxycoprostaneMeSH, HMDB
(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12-triolHMDB
(3α,5β,7α,12α)-Cholestane-3,7,12-triolHMDB
5beta-Cholestan-3alpha,7alpha,12alpha-triolHMDB
5β-Cholestan-3α,7α,12α-triolHMDB
Chemical FormulaC27H48O3
Average Molecular Weight420.6682
Monoisotopic Molecular Weight420.360345402
IUPAC Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
Traditional Name(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol
CAS Registry Number547-96-6
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)C
InChI Identifier
InChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyRIVQQZVHIVNQFH-XJZYBRFWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP10(4.78) g/LALOGPS
logP10(4.98) g/LChemAxon
logS10(-4.9) g/LALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.87 m³·mol⁻¹ChemAxon
Polarizability52.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+205.72631661259
DarkChem[M-H]-202.87831661259
AllCCS[M+H]+209.59332859911
AllCCS[M-H]-204.45632859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TMS,#1CC(C)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)C3231.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TMS,#2CC(C)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]3O3291.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TMS,#3CC(C)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]3O3292.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TMS,#1CC(C)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)C3242.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TMS,#2CC(C)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)C3222.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TMS,#3CC(C)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]3O3242.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,3TMS,#1CC(C)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)C3252.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TBDMS,#1CC(C)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)C3465.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TBDMS,#2CC(C)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]3O3528.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,1TBDMS,#3CC(C)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]3O3531.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TBDMS,#1CC(C)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)C3701.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TBDMS,#2CC(C)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)C3668.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,2TBDMS,#3CC(C)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]3O3706.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
5beta-Cholestane-3alpha,7alpha,12alpha-triol,3TBDMS,#1CC(C)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)C3930.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kkc-0349300000-7324287f0b234066bd642017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3210079000-e1f273aa178918c831742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 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 - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Positive-QTOFsplash10-0udr-0007900000-f9ed4dff04df44d2af492016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Positive-QTOFsplash10-0f79-2209400000-84e3ed6130fdfe17578f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Positive-QTOFsplash10-00di-5209000000-1166d5a4d66dea526dfc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Negative-QTOFsplash10-014i-0001900000-766e9dee4a7aba343c982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Negative-QTOFsplash10-0uxr-0001900000-90680fd53f8266be1ace2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Negative-QTOFsplash10-0f79-2209400000-a1dd0a941d753b0d75e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Negative-QTOFsplash10-014i-0000900000-722417cd9cab9945ab4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Negative-QTOFsplash10-014i-0000900000-722417cd9cab9945ab4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Negative-QTOFsplash10-014i-0010900000-aeb99a2e383b60fbc7442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 10V, Positive-QTOFsplash10-00di-0001900000-f143819ead264249729e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 20V, Positive-QTOFsplash10-0abi-9122200000-2f2c0b60a02fc711aa0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5beta-Cholestane-3alpha,7alpha,12alpha-triol 40V, Positive-QTOFsplash10-0a4i-9721000000-6687d50233adfbaf76042021-09-24Wishart 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 IDFDB022635
KNApSAcK IDNot Available
Chemspider ID141053
KEGG Compound IDC05454
BioCyc IDNot Available
BiGG ID45846
Wikipedia LinkNot Available
METLIN ID6254
PubChem Compound160520
PDB IDNot Available
ChEBI ID16496
Food Biomarker OntologyNot Available
VMH IDXOLTRIOL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shimazu K, Kuwabara M, Yoshii M, Kihira K, Takeuchi H, Nakano I, Ozawa S, Onuki M, Hatta Y, Hoshita T: Bile alcohol profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis. J Biochem. 1986 Feb;99(2):477-83. [PubMed:3700361 ]
  2. Oftebro H, Bjorkhem I, Skrede S, Schreiner A, Pederson JI: Cerebrotendinous xanthomatosis: a defect in mitochondrial 26-hydroxylation required for normal biosynthesis of cholic acid. J Clin Invest. 1980 Jun;65(6):1418-30. [PubMed:7410549 ]
  3. Axen E, Postlind H, Sjoberg H, Wikvall K: Liver mitochondrial cytochrome P450 CYP27 and recombinant-expressed human CYP27 catalyze 1 alpha-hydroxylation of 25-hydroxyvitamin D3. Proc Natl Acad Sci U S A. 1994 Oct 11;91(21):10014-8. [PubMed:7937829 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NAD → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
5beta-Cholestane-3alpha,7alpha,12alpha-triol + NADP → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADPH + Hydrogen Iondetails
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 + NADPH + Oxygen → Coprocholic acid + NADP + Waterdetails
5beta-Cholestane-3alpha,7alpha,12alpha-triol + Oxygen + NADPH → 27-Deoxy-5b-cyprinol + NADP + Waterdetails