Showing metabocard for 7a-Hydroxy-cholestene-3-one (BMDB0001993)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:42 UTC
Update Date2020-05-21 16:28:48 UTC
BMDB IDBMDB0001993
Secondary Accession Numbers
  • BMDB01993
Metabolite Identification
Common Name7a-Hydroxy-cholestene-3-one
Description7a-Hydroxy-cholestene-3-one, also known as cholest-4-en-7alpha-ol-3-one or 7 alpha-3ox-C, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7a-hydroxy-cholestene-3-one is considered to be a bile acid lipid molecule. 7a-Hydroxy-cholestene-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7alpha-Hydroxy-4-cholesten-3-oneChEBI
Cholest-4-en-7alpha-ol-3-oneChEBI
7a-Hydroxy-4-cholesten-3-oneGenerator
7Α-hydroxy-4-cholesten-3-oneGenerator
Cholest-4-en-7a-ol-3-oneGenerator
Cholest-4-en-7α-ol-3-oneGenerator
7 alpha-3Ox-CHMDB
7 alpha-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxy-4-cholesten-3-oneHMDB
7-a-Hydroxycholest-4-en-3-oneHMDB
7-alpha-Hydroxy-4-cholesten-3-oneHMDB
7-alpha-Hydroxycholest-4-en-3-oneHMDB
7-Hydroxycholest-4-en-3-oneHMDB
7a-Hydroxy-4-cholesten-3-one-12alphaHMDB
7alpha-Hydroxycholest-4-en-3-oneHMDB
HCOHMDB
Cholest-4-en-7 alpha-ol-3-oneHMDB
7-Hydroxy-4-cholesten-3-oneHMDB
Chemical FormulaC27H44O2
Average Molecular Weight400.6371
Monoisotopic Molecular Weight400.334130652
IUPAC Name(1S,2R,9R,10S,11S,14R,15R)-9-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name7α-hydroxy-4-cholesten-3-one
CAS Registry Number3862-25-7
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
InChI Identifier
InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChI KeyIOIZWEJGGCZDOL-RQDYSCIWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives 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
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.46ALOGPS
logP6.37ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.16 m³·mol⁻¹ChemAxon
Polarizability50.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-00dr-1339000000-8b87f8914863b4c7e8e7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a6r-4672900000-f5cd21522bdf7607c5cbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0019500000-764a74c3942ad452aa8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-3339100000-87e6e598932d57a6274eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-8469000000-b55e4f0de6f6dbfbe093View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-b03a7cbfe5ca7374d51fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-903f15d46f6bf7449623View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1009000000-fd9c44e4f27a3c62b7e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0001900000-7ee7f5ca27c449403c35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvl-9246300000-d08ac46b391d42697238View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9620000000-e3dea04967eb9e6421c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-dc23ba87137530d83f68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-dc23ba87137530d83f68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-75e53e521203e582561bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001993
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022786
KNApSAcK IDNot Available
Chemspider ID110306
KEGG Compound IDC05455
BioCyc IDNot Available
BiGG ID45848
Wikipedia LinkNot Available
METLIN ID6419
PubChem Compound123743
PDB IDNot Available
ChEBI ID17899
References
Synthesis ReferenceAlexander, David L.; Fisher, Jed F. A convenient synthesis of 7a-hydroxycholest-4-en-3-one by the hydroxypropyl-b-cyclodextrin-facilitated cholesterol oxidase oxidation of 3b,7a-cholest-5-ene-3,7-diol. Steroids (1995), 60(3), 290-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Prostacyclin synthase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
PTGIS
Uniprot ID:
Q29626
Molecular weight:
56629.0
Reactions
7a-Hydroxy-cholestene-3-one + NADPH + Oxygen → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Waterdetails
Enzyme Details
2. Dihydrodiol dehydrogenase 3
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P52898
Molecular weight:
36784.0
Reactions
7a-Hydroxy-cholestene-3-one + NADPH → 7a-Hydroxy-5b-cholestan-3-one + NADPdetails