Epipregnanolone (CHEM035232)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:35:44 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035232
Identification
Common NameEpipregnanolone
ClassSmall Molecule
DescriptionThe 3beta-stereoisomer of 3-hydroxy-5beta-pregnan-20-one.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,5beta)-3-Hydroxypregnan-20-oneChEBI
3beta-Hydroxy-5beta-pregnane-20-oneChEBI
3beta-Hydroxy-5beta-tetrahydroprogesteroneChEBI
(3b,5b)-3-Hydroxypregnan-20-oneGenerator
(3Β,5β)-3-hydroxypregnan-20-oneGenerator
3b-Hydroxy-5b-pregnane-20-oneGenerator
3Β-hydroxy-5β-pregnane-20-oneGenerator
3b-Hydroxy-5b-tetrahydroprogesteroneGenerator
3Β-hydroxy-5β-tetrahydroprogesteroneGenerator
3-deoxo-3b-Hydroxy-5b-dihydroprogesteroneHMDB
3b,5b-PregnanoloneHMDB
3b-Hydroxy-5b-pregnan-20-oneHMDB, Generator
5b-Pregnan-3b-ol-20-oneHMDB
5b-Pregnane-3b-hydroxy-20-oneHMDB
5b-Pregnane-3b-ol-20-oneHMDB
Pregnanolone IHMDB
3-Hydroxypregnan-20-oneMeSH, HMDB
Pregnanolone, (3beta)-isomerMeSH, HMDB
3 Hydroxypregnan 20 oneMeSH, HMDB
EpipregnanoloneChEBI
3Β-hydroxy-5β-pregnan-20-oneGenerator, HMDB
3-Deoxo-3beta-hydroxy-5beta-dihydroprogesteroneHMDB
3-Deoxo-3β-hydroxy-5β-dihydroprogesteroneHMDB
3beta,5beta-PregnanoloneHMDB
3beta-Hydroxy-5beta-pregnan-20-oneHMDB
3β,5β-PregnanoloneHMDB
5beta-Pregnan-3beta-ol-20-oneHMDB
5beta-Pregnane-3beta-hydroxy-20-oneHMDB
5beta-Pregnane-3beta-ol-20-oneHMDB
5β-Pregnan-3β-ol-20-oneHMDB
5β-Pregnane-3β-hydroxy-20-oneHMDB
5β-Pregnane-3β-ol-20-oneHMDB
Chemical FormulaC21H34O2
Average Molecular Mass318.494 g/mol
Monoisotopic Mass318.256 g/mol
CAS Registry Number128-21-2
IUPAC Name1-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one
Traditional Name1-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone
SMILES[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16+,17-,18+,19+,20+,21-/m1/s1
InChI KeyAURFZBICLPNKBZ-GRWISUQFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • Oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.0014 g/LALOGPS
logP4.28ALOGPS
logP3.99ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability38.26 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-4900000000-39156fa655392898752fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-4900000000-39156fa655392898752fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb08Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-82b5328b4643c0421b0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1496000000-6fd25d5861771fb104b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002o-2490000000-ba6e2bc4d584ea3d3a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-826f869c8c8e3739b52eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0059000000-699658e7c96cdaee62e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zmr-1092000000-19955e9b1f2b26db2425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0029000000-ac1c6a15538469151b6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ks-0093000000-db70f670eb2440b743f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-5b53b3ba37ccafca449fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lgi-1797000000-c11629ffa10cac4be118Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-8910000000-2813a600e98ff5997275Spectrum
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 IDHMDB0001471
FooDB IDFDB022642
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEpipregnanolone
Chemspider ID198867
ChEBI ID16229
PubChem Compound ID228491
Kegg Compound IDC11825
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1265794
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17583491
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=347637