Showing metabocard for 3b,17a,21-Trihydroxypregnenone (BMDB0000382)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:29:41 UTC
Update Date2020-04-22 15:03:17 UTC
BMDB IDBMDB0000382
Secondary Accession Numbers
  • BMDB00382
Metabolite Identification
Common Name3b,17a,21-Trihydroxypregnenone
Description3b,17a,21-Trihydroxypregnenone 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. Based on a literature review very few articles have been published on 3b,17a,21-Trihydroxypregnenone.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17,21-DihydroxypregnenoloneHMDB
17a,21-DihydroxypregnenoloneHMDB
3b,17a,21-Trihydroxypregn-5-en-20-oneHMDB
Chemical FormulaC21H32O4
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
IUPAC Name(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
Traditional Name(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
CAS Registry Number1167-48-2
SMILES
[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C
InChI Identifier
InChI=1S/C21H32O4/c1-19-7-5-17-15(16(19)6-8-21(19,25)9-10-22)4-3-13-11-14(23)12-18(24)20(13,17)2/h12-13,15-17,22-23,25H,3-11H2,1-2H3/t13?,15-,16-,17-,19-,20-,21-/m0/s1
InChI KeyRJKJQHWLCLYSHD-DGFNXGTDSA-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-hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic alcohol
  • Vinylogous acid
  • Ketone
  • Enol
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.33ALOGPS
logP2.39ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.84 m³·mol⁻¹ChemAxon
Polarizability40.01 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, Positivesplash10-0ac0-0369000000-694e0c72dd64e70fc3ddView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-0005490000-737a75026d200b124effView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-967157175001bc9e75f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-1079000000-fae9927a20f423bb18d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0391000000-67df0076cd3b56f05e2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-b0c86c6c2045af9c615fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-2039000000-11c78060fb294c973a6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufs-2096000000-3363853b2696c35f7845View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000382
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022000
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHeer, J.; Miescher, K. Steroids. CIV. The synthesis of the dihydroxyacetone side chain in the steroid series. Helvetica Chimica Acta (1951), 34 359-72.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available