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Record Information
Version4.0
Creation Date2009-07-13 12:46:54 UTC
Update Date2017-09-27 08:27:05 UTC
HMDB IDHMDB0012454
Secondary Accession Numbers
  • HMDB12454
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 KeyGYJSAWZGYQXRBS-BJGNZVHYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Indirect biological role:

Industrial application:

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.75 m³·mol⁻¹ChemAxon
Polarizability51.24 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, Positivesplash10-0v4r-0256900000-22ef0ff1c4df41e32aa6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1110149000-52df634bab9d2c969872View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0007900000-e8ca8081a306a092d104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1019200000-b40afd412ea2d89a54fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-3129000000-db65dd1760e756700c39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0001900000-4f85260592d4f598f51aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ar-0008900000-8bd8be731b8d868d5b3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7009100000-2d5bb37e8b58d53d88a6View 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 IDFDB029070
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17335
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481408
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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