Showing metabocard for 7 alpha,26-Dihydroxy-4-cholesten-3-one (BMDB0012459)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:58 UTC
Update Date2020-05-21 16:28:49 UTC
BMDB IDBMDB0012459
Secondary Accession Numbers
  • BMDB12459
Metabolite Identification
Common Name7 alpha,26-Dihydroxy-4-cholesten-3-one
Description7 alpha,26-Dihydroxy-4-cholesten-3-one, also known as 4-cholesten-7alpha,26-diol-3-one or 7,26-dhxyclso, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. 7 alpha,26-Dihydroxy-4-cholesten-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7 a,26-Dihydroxy-4-cholesten-3-oneGenerator
7 Α,26-dihydroxy-4-cholesten-3-oneGenerator
(7alpha)-7,26-Dihydroxy-cholest-4-en-3-oneHMDB
4-Cholesten-7alpha,26-diol-3-oneHMDB
7,26-DhxyclsoHMDB
7alpha,26-Dihydroxy-4-cholesten-3-oneHMDB
7alpha,26-Dihydroxycholest-4-en-3-oneHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,9R,15R)-9-hydroxy-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry Number4675-38-1
SMILES
CC(CO)CCC[C@@H](C)C1CCC2C3[C@H](O)CC4=CC(=O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H44O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h14,17-18,21-25,28,30H,5-13,15-16H2,1-4H3/t17?,18-,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI KeyKVJVJJWIEXCECB-JZGXDVPNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives 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
  • 26-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Fatty alcohol
  • Cyclohexenone
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Cyclic ketone
  • Ketone
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP4.6ALOGPS
logP5.01ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)-0.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.01 m³·mol⁻¹ChemAxon
Polarizability50.79 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, Positivesplash10-0f79-0359200000-c5e766bc8da3445acdeaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-1220390000-2ea93ad32d390af352daView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009200000-f13064ffc70da2c2b57dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00l2-1009000000-f344cdc48d7b49f22d6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-3129000000-b6c48651e7e9ac09edbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004900000-7754503899cd9db211c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009600000-54c6b067e6490ab83b85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0674-2009000000-ceacf291ac96437f5944View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0006900000-1bab66a6ddf2f8b577e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07wj-5749100000-fb55e94ae37f95aa32a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9850000000-4478cbe8a6ea3e417fe2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-67ea14fb7a26b9b2d929View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0005900000-37c9645751a2f52b7424View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0004900000-ca04c33318a7e2c042bcView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012459
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029075
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC17336
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481412
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B
Uniprot ID:
P14893
Molecular weight:
42220.0
Reactions
7-a,27-dihydroxycholesterol + NADP → 7 alpha,26-Dihydroxy-4-cholesten-3-one + NADPHdetails