You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2009-07-13 13:38:40 UTC
Update Date2017-03-02 21:32:33 UTC
HMDB IDHMDB12458
Secondary Accession NumbersNone
Metabolite Identification
Common Name7 alpha-Hydroxy-3-oxo-4-cholestenoate
Description7 alpha-Hydroxy-3-oxo-4-cholestenoate is involved in the primary bile acid biosynthesis pathway. 7 alpha-Hydroxy-3-oxo-4-cholestenoate is created from either 3 beta,7 alpha-Dihydroxy-5-cholestenoate or 7 alpha,26-Dihydroxy-4-cholesten-3-one through the actions of HSD3B7 (EC:1.1.1.181) or CYP27A (E1.14.13.15), respectively.
Structure
Thumb
Synonyms
ValueSource
(7alpha)7-Hydroxy-3-oxo--cholest-4-en-26-OateHMDB
(7alpha)7-Hydroxy-3-oxo--cholest-4-en-26-Oic acidHMDB
7-HocaHMDB
7alpha-Hydroxy-3-oxo-4-cholestenoateHMDB
7alpha-Hydroxy-3-oxo-4-cholestenoic acidHMDB
Chemical FormulaC27H42O4
Average Molecular Weight430.62
Monoisotopic Molecular Weight430.308309832
IUPAC Name(6R)-6-[(2R,9R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-methylheptanoic acid
Traditional Name(6R)-6-[(2R,9R,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-methylheptanoic acid
CAS Registry Number115538-85-7
SMILES
C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C
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-KFNQEEOWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid 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 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 Solubility0.0037 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.85 m3·mol-1ChemAxon
Polarizability50.77 Å3ChemAxon
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 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 IDFDB029074
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17337
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12458
Metagene LinkHMDB12458
METLIN IDNot Available
PubChem Compound53481411
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:
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 → 7 alpha-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
3 beta,7 alpha-Dihydroxy-5-cholestenoate + NAD → 7 alpha-Hydroxy-3-oxo-4-cholestenoate + NADH + Hydrogen Iondetails