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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-13 13:38:40 UTC
Update Date2017-11-17 18:34:40 UTC
HMDB IDHMDB0012458
Secondary Accession Numbers
  • HMDB12458
Metabolite Identification
Common Name7alpha-Hydroxy-3-oxo-4-cholestenoate
Description7alpha-Hydroxy-3-oxo-4-cholestenoate is involved in the primary bile acid biosynthesis pathway. 7alpha-Hydroxy-3-oxo-4-cholestenoate is created from either 3beta,7alpha-Dihydroxy-5-cholestenoate or 7alpha,26-Dihydroxy-4-cholesten-3-one through the actions of HSD3B7 (EC:1.1.1.181) or CYP27A (EC:1.14.13.15), respectively.
Structure
Thumb
Synonyms
ValueSource
7-HocaChEBI
7a-Hydroxy-3-oxo-4-cholestenoateGenerator
7a-Hydroxy-3-oxo-4-cholestenoic acidGenerator
7alpha-Hydroxy-3-oxo-4-cholestenoateGenerator
7α-hydroxy-3-oxo-4-cholestenoateGenerator
7α-hydroxy-3-oxo-4-cholestenoic acidGenerator
7 alpha-Hydroxy-3-oxo-4-cholestenoic acidMeSH
(7α)-7-Hydroxy-3-oxocholest-4-en-26-oic acidCAS
(7α)-7-hydroxy-3-oxocholest-4-en-26-oateCAS
7α-Hydroxy-3-oxocholest-4-en-26-oic acidCAS
(7alpha)-7-Hydroxy-3-oxocholest-4-en-26-oic acidCAS
(7alpha)-7-hydroxy-3-oxocholest-4-en-26-oateCAS
7alpha-Hydroxy-3-oxocholest-4-en-26-oic acidCAS
Chemical FormulaC27H42O4
Average Molecular Weight430.629
Monoisotopic Molecular Weight430.308309832
IUPAC Name(6R)-6-[(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-methylheptanoic acid
CAS Registry Number115538-85-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
InChI Identifier
InChI=1S/C27H42O4/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/h14,16-17,20-24,29H,5-13,15H2,1-4H3,(H,30,31)/t16-,17?,20-,21+,22+,23-,24+,26+,27-/m1/s1
InChI KeySATGKQGFUDXGAX-MYWFJNCASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • Steroid acid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Medium-chain fatty acid
  • Cyclohexenone
  • Hydroxy fatty acid
  • Fatty acyl
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

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 Solubility0.0037 g/LALOGPS
logP4.05ALOGPS
logP5.31ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.85 m³·mol⁻¹ChemAxon
Polarizability51.45 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
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 IDFDB029074
KNApSAcK IDNot Available
Chemspider ID2338765
KEGG Compound IDC17337
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3081085
PDB IDNot Available
ChEBI ID83036
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:
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
7 alpha,26-Dihydroxy-4-cholesten-3-one + Oxygen + NADPH + Hydrogen Ion → 7alpha-Hydroxy-3-oxo-4-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
3beta,7alpha-Dihydroxy-5-cholestenoate + NAD → 7alpha-Hydroxy-3-oxo-4-cholestenoate + NADH + Hydrogen Iondetails