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Showing Compound Epipregnanolone (FDB022642)

Record Information
Version1.0
Creation date2011-09-21 00:17:19 UTC
Update date2015-07-21 06:57:17 UTC
Primary IDFDB022642
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number128-21-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
(3β,5β)-3-hydroxypregnan-20-oneGenerator
3-Deoxo-3b-hydroxy-5b-dihydroprogesteronehmdb
3β-hydroxy-5β-pregnane-20-oneGenerator
3β-hydroxy-5β-tetrahydroprogesteroneGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H34O2
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
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
Isomeric 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
Average Molecular Weight318.4935
Monoisotopic Molecular Weight318.255880332
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSEpipregnanolone, non-derivatized, GC-MS Spectrumsplash10-0udr-4900000000-39156fa655392898752fSpectrum
GC-MSEpipregnanolone, non-derivatized, GC-MS Spectrumsplash10-0udr-4900000000-39156fa655392898752fSpectrum
Predicted GC-MSEpipregnanolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb08Spectrum
Predicted GC-MSEpipregnanolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086eSpectrum
Predicted GC-MSEpipregnanolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-82b5328b4643c0421b0d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-1496000000-6fd25d5861771fb104b72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002o-2490000000-ba6e2bc4d584ea3d3a4b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-826f869c8c8e3739b52e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0059000000-699658e7c96cdaee62e82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zmr-1092000000-19955e9b1f2b26db24252017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0029000000-ac1c6a15538469151b6c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ks-0093000000-db70f670eb2440b743f92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-5b53b3ba37ccafca449f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lgi-1797000000-c11629ffa10cac4be1182021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-8910000000-2813a600e98ff59972752021-09-24View Spectrum
NMRNot Available
ChemSpider ID198867
ChEMBL IDCHEMBL1908049
KEGG Compound IDC11825
Pubchem Compound ID228491
Pubchem Substance IDNot Available
ChEBI ID16229
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01471
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference