Showing metabocard for Epipregnanolone (BMDB0001471)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:25 UTC
Update Date2020-04-22 15:08:19 UTC
BMDB IDBMDB0001471
Secondary Accession Numbers
  • BMDB01471
Metabolite Identification
Common NameEpipregnanolone
DescriptionEpipregnanolone 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. Thus, epipregnanolone is considered to be a steroid. Based on a literature review a significant number of articles have been published on Epipregnanolone.
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 Weight318.4935
Monoisotopic Molecular Weight318.255880332
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
CAS Registry Number128-21-2
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O
InChI Identifier
InChI=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
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-4900000000-39156fa655392898752fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udr-4900000000-39156fa655392898752fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb08View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-82b5328b4643c0421b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1496000000-6fd25d5861771fb104b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002o-2490000000-ba6e2bc4d584ea3d3a4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-826f869c8c8e3739b52eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0059000000-699658e7c96cdaee62e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zmr-1092000000-19955e9b1f2b26db2425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0029000000-ac1c6a15538469151b6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ks-0093000000-db70f670eb2440b743f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-5b53b3ba37ccafca449fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lgi-1797000000-c11629ffa10cac4be118View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-8910000000-2813a600e98ff5997275View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001471
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022642
KNApSAcK IDNot Available
Chemspider ID198867
KEGG Compound IDC11825
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpipregnanolone
METLIN IDNot Available
PubChem Compound228491
PDB IDNot Available
ChEBI ID16229
References
Synthesis ReferenceHalpern, Otto. Pregnenolones and androstenolones. U.S. (1969), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available