3b,17a,21-Trihydroxypregnenone (CHEM034832)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:15:39 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034832
Identification
Common Name3b,17a,21-Trihydroxypregnenone
ClassSmall Molecule
Description3b,17a,21-Trihydroxypregnenone is an intermediate in the human fetus at midpregnancy converting it to cortisol (PMID 4231965). It has been found as an intermediate in alternative pathways in human adrenal steroidogenesis that take place under in vitro conditions of normal adrenal slices from patients with hypernephroid kidney carcinomas that bypass cholesterol, pregnenolone, progesterone and proceed to 21-hydroxypregnenolone (PMID 6247575) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17,21-DihydroxypregnenoloneHMDB
17a,21-DihydroxypregnenoloneHMDB
3b,17a,21-Trihydroxypregn-5-en-20-oneHMDB
Chemical FormulaC21H32O4
Average Molecular Mass348.476 g/mol
Monoisotopic Mass348.230 g/mol
CAS Registry Number1167-48-2
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
SMILES[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ac0-0369000000-694e0c72dd64e70fc3ddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-0005490000-737a75026d200b124effSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-967157175001bc9e75f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-1079000000-fae9927a20f423bb18d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fr-0391000000-67df0076cd3b56f05e2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-b0c86c6c2045af9c615fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-2039000000-11c78060fb294c973a6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufs-2096000000-3363853b2696c35f7845Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000382
FooDB IDFDB022000
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available