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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 08:24:07 UTC
HMDB IDHMDB0001457
Secondary Accession Numbers
  • HMDB01457
Metabolite Identification
Common Name5-b-Cholestane-3a ,7a ,12a-triol
Description5-b-Cholestane-3a ,7a ,12a-triol is an intermediate in Bile acid biosynthesis. 5-b-Cholestane-3a ,7a ,12a-triol is the second to last step of synthesis of 5beta-Cyprinolsulfate. It is converted from 7alpha,12alpha-Dihydroxy-5beta-cholestan-3-one via enzymatic reaction then it is coneverted to 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 cataylzes it is classified as a small molecule reaction. (BioCyc).
Structure
Thumb
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
5-beta-Cholestane-3-alpha,7-alpha,12-alpha-triolHMDB
3,7,12-TrihydroxycholestaneMeSH
3,7,12-TrihydroxycoprostaneMeSH
3,7,12-Trihydroxycoprostane, (3alpha,5alpha,7alpha,12alpha)-isomerMeSH
3,7,12-Trihydroxycoprostane, (3beta,5alpha,7alpha,12alpha)-isomerMeSH
3,7,12-Trihydroxycoprostane, (3beta,5beta,7alpha,12alpha)-isomerMeSH
3alpha, 7alpha,12alpha-Trihydroxy-5beta-cholestaneMeSH
5 beta-Cholestane-3 alpha,7 alpha,12 alpha-triolMeSH
5beta-Cholestane-3alpha,7alpha,12alpha-triolMeSH
ChtriolMeSH
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol
Traditional Nametrihydroxycoprostane
CAS Registry NumberNot Available
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
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These 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:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Indirect biological role:

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP4.78ALOGPS
logP4.98ChemAxon
logS-4.9ALOGPS
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
Polarizability52.37 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kkc-0349300000-7324287f0b234066bd64View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3210079000-e1f273aa178918c83174View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0007900000-f9ed4dff04df44d2af49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-2209400000-84e3ed6130fdfe17578fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-5209000000-1166d5a4d66dea526dfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-766e9dee4a7aba343c98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-0001900000-90680fd53f8266be1aceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-2209400000-a1dd0a941d753b0d75e7View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
27-Hydroxylase DeficiencyPw000697Pw000697 greyscalePw000697 simpleNot Available
Bile Acid BiosynthesisPw000145Pw000145 greyscalePw000145 simpleMap00120
Cerebrotendinous Xanthomatosis (CTX)Pw000196Pw000196 greyscalePw000196 simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIPw000192Pw000192 greyscalePw000192 simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIIPw000193Pw000193 greyscalePw000193 simpleNot Available
Displaying entries 1 - 5 of 7 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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
5-b-Cholestane-3a ,7a ,12a-triol + NAD → 7a,12a-Dihydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
5-b-Cholestane-3a ,7a ,12a-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
5-b-Cholestane-3a ,7a ,12a-triol + NADPH + Oxygen → 3a,7a,12a-Trihydroxy-5b-cholestanoic acid + NADP + Waterdetails
5-b-Cholestane-3a ,7a ,12a-triol + Oxygen + NADPH → 27-Deoxy-5b-cyprinol + NADP + Waterdetails