Showing metabocard for 3a,7a-Dihydroxy-5b-cholestanate (BMDB0003851)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:22 UTC
Update Date2020-04-22 15:12:50 UTC
BMDB IDBMDB0003851
Secondary Accession Numbers
  • BMDB03851
Metabolite Identification
Common Name3a,7a-Dihydroxy-5b-cholestanate
Description3a,7a-Dihydroxy-5b-cholestanate belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. 3a,7a-Dihydroxy-5b-cholestanate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3a,7a-Dihydroxy-5b-cholestanic acidGenerator
17,20a-Dihydroxy-4-pregnen-3-oneHMDB
17,20a-Dihydroxy-pregn-4-en-3-oneHMDB
17a,20a-Dihydroxy-4-pregnen-3-oneHMDB
17a,20a-Dihydroxypregn-4-ene-3-oneHMDB
17a,20a-DihydroxyprogesteroneHMDB
17a-Hydroxy-20a-dihydroprogesteroneHMDB
20a-DihydroxyprogesteroneHMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanateHMDB
Pregn-4-ene-17a,20a-diol-3-oneHMDB
(20S)-Isomer OF 17,20-dihydroxy-4-pregnen-3-oneMeSH
17 alpha,20 alpha-DihydroxyprogesteroneMeSH
17,20 beta-Dihydroxy-4-pregnen-3-oneMeSH
17,20-Dihydroxy-4-pregnen-3-oneMeSH
17,20beta-PMeSH
17,20beta-Dihydroxy-4-pregnen-3-oneMeSH
17a,20a-DHPMeSH
17alpha,20beta-DPMeSH
4-Pregnene-17 alpha,20 alpha-diol-3-oneMeSH
Maturation-inducing steroidMeSH
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name(1S,2R,10R,11S,14S,15S)-14-hydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name20a-dihydroxyprogesterone
CAS Registry Number652-69-7
SMILES
[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-19-8-5-15(23)13-14(19)3-4-16-17(19)6-9-20(2)18(16)7-10-21(20,24)11-12-22/h13,16-18,22,24H,3-12H2,1-2H3/t16-,17+,18+,19+,20+,21+/m1/s1
InChI KeyABBVGECYEGYVPY-CEGNMAFCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Primary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • 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
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP5.321Not Available
Predicted Properties
PropertyValueSource
logP2.79ALOGPS
logP2.66ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)14.28ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.48 m³·mol⁻¹ChemAxon
Polarizability39.13 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, Positivesplash10-0zfr-1449000000-bfa16ef83b90784d40a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-0012900000-349e5a97e3325197fb2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0039000000-4652fc5a5294ba58b6cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1294000000-45676693ab4540441aa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000e-0790000000-d49b24da1e0d33760603View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-ddefd96e63616438bd3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-2049000000-aee0d0194e639b1a9cb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-1093000000-b3765702e3dbc4293fabView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003851
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023238
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107835
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceAl-Awadi, Sameera; Afzal, Mohammed; Oommen, Sosamma. Studies on Geobacillus stearothermophilus-part V1: transformation of 17a-hydroxyprogesterone and 21-hydroxyprogesterone. Biocatalysis and Biotransformation (2007), 25(1), 43-50.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available