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Record Information
Version3.6
Creation Date2009-07-13 12:46:54 UTC
Update Date2016-02-11 01:24:48 UTC
HMDB IDHMDB12454
Secondary Accession NumbersNone
Metabolite Identification
Common Name3 beta,7 alpha-Dihydroxy-5-cholestenoate
Description3 beta,7 alpha-Dihydroxy-5-cholestenoate is found in the primary bile acid biosynthesis pathway. 3 beta,7 alpha-Dihydroxy-5-cholestenoate is created from 3 beta-Hydroxy-5-cholestenoate through the action of CYP7B (E1.14.13.100). 3 beta,7 alpha-Dihydroxy-5-cholestenoate is then converted to 7 alpha-Hydroxy-3-oxo-4-cholestenoate by the action of HSD3B7 (EC:1.1.1.181).
Structure
Thumb
Synonyms
ValueSource
(3beta,7alpha)-3,7-Dihydroxy-cholest-5-en-26-OateHMDB
(3beta,7alpha)-3,7-Dihydroxy-cholest-5-en-26-Oic acidHMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-OateHMDB
3 beta,7 alpha-Dihydroxy-5-cholesten-26-Oic acidHMDB
3,7-Dihydroxy-5-cholestenoateHMDB
3,7-Dihydroxy-5-cholestenoic acidHMDB
3beta,7alpha-Dihydroxy-5-cholesten-26-OateHMDB
3beta,7alpha-Dihydroxy-5-cholesten-26-Oic acidHMDB
Chemical FormulaC27H44O4
Average Molecular Weight432.6359
Monoisotopic Molecular Weight432.323959896
IUPAC Name(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(2R,5S,9S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]-2-methylheptanoic acid
CAS Registry Number115538-84-6
SMILES
C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H44O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20?,21?,22?,23-,24?,26+,27-/m1/s1
InChI KeyInChIKey=GYJSAWZGYQXRBS-BJGNZVHYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. These are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Medium-chain fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 Solubility0.0069 mg/mLALOGPS
logP3.92ALOGPS
logP4.9ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.75 m3·mol-1ChemAxon
Polarizability51.24 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
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 IDFDB029070
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17335
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12454
Metagene LinkHMDB12454
METLIN IDNot Available
PubChem Compound53481408
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
3 beta-Hydroxy-5-cholestenoate + Oxygen + NADPH + Hydrogen Ion → 3 beta,7 alpha-Dihydroxy-5-cholestenoate + NADP + Waterdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265
Reactions
3 beta,7 alpha-Dihydroxy-5-cholestenoate + NAD → 7 alpha-Hydroxy-3-oxo-4-cholestenoate + NADH + Hydrogen Iondetails