Alloepipregnanolone (CHEM035226)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:35:29 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035226
Identification
Common NameAlloepipregnanolone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,5alpha)-3-Hydroxypregnan-20-oneChEBI
3beta-Hydroxy-5alpha-pregnane-20-oneChEBI
5alpha-Pregnan-3beta-ol-20-oneChEBI
Allopregnan-3beta-ol-20-oneChEBI
EpiallopregnanoloneKegg
3beta-Hydroxy-5alpha-pregnan-20-oneKegg
(3b,5a)-3-Hydroxypregnan-20-oneGenerator
(3Β,5α)-3-hydroxypregnan-20-oneGenerator
3b-Hydroxy-5a-pregnane-20-oneGenerator
3Β-hydroxy-5α-pregnane-20-oneGenerator
5a-Pregnan-3b-ol-20-oneGenerator
5Α-pregnan-3β-ol-20-oneGenerator
Allopregnan-3b-ol-20-oneGenerator
Allopregnan-3β-ol-20-oneGenerator
3b-Hydroxy-5a-pregnan-20-oneGenerator
3Β-hydroxy-5α-pregnan-20-oneGenerator
3 Hydroxypregnan 20 oneMeSH
3 alpha Hydroxy 5 alpha pregnan 20 oneMeSH
3 alpha Hydroxy 5 beta pregnan 20 oneMeSH
3 alpha, 5 beta TetrahydroprogesteroneMeSH
3 alpha, 5 beta-TetrahydroprogesteroneMeSH
3 alpha-Hydroxy-5 alpha-pregnan-20-oneMeSH
3 alpha-Hydroxy-5 beta-pregnan-20-oneMeSH
3-Hydroxypregnan-20-oneMeSH
3beta Hydroxy 5alpha pregnan 20 oneMeSH
Allopregnan 3 beta ol 20 oneMeSH
Allopregnan-3 beta-ol-20-oneMeSH
EltanoloneMeSH
EpipregnanoloneMeSH
Pregnan 3alpha ol 20 oneMeSH
Pregnan-3alpha-ol-20-oneMeSH
PregnanoloneMeSH
Pregnanolone, (3alpha)-isomerMeSH
Pregnanolone, (3alpha, 5beta, 17-alpha)-isomerMeSH
Pregnanolone, (3alpha,5alpha)-isomerMeSH
Pregnanolone, (3alpha,5beta)-isomerMeSH
Pregnanolone, (3beta)-isomerMeSH
Pregnanolone, (3beta, 5alpha)-isomerMeSH
Pregnanolone, (3beta, 5alpha, 17alpha)-isomerMeSH
Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomerMeSH
Pregnanolone, (3beta, 5beta)-isomerMeSH
Pregnanolone, (3beta, 5beta, 17alpha)-isomerMeSH
Pregnanolone, (3beta, 5beta,14beta)-isomerMeSH
Pregnanolone, (5alpha)-isomerMeSH
SepranoloneMeSH
alpha-Hydroxy-5 alpha-pregnan-20-one, 3MeSH
alpha-Hydroxy-5 beta-pregnan-20-one, 3MeSH
alpha-Pregnan-20-one, 3 alpha-hydroxy-5MeSH
beta-Ol-20-one, allopregnan-3MeSH
beta-Pregnan-20-one, 3 alpha-hydroxy-5MeSH
3-deoxo-3b-Hydroxy-5a-dihydroprogesteroneHMDB
3b-AllopregnanoloneHMDB
3b-Hydroxy-5a,17b-pregnan-20-oneHMDB
3b-Hydroxy-5a-tetrahydroprogesteroneHMDB
5a-DihydropregnenoloneHMDB
5a-Pregnane-3b-ol-20-oneHMDB
AllopregnanoloneHMDB, MeSH
IsopregnanoloneHMDB
Chemical FormulaC21H34O2
Average Molecular Mass318.494 g/mol
Monoisotopic Mass318.256 g/mol
CAS Registry Number516-55-2
IUPAC Name1-[(1S,2S,5S,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one
Traditional Nameisopregnanolone
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+/m0/s1
InChI KeyAURFZBICLPNKBZ-FZCSVUEKSA-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
  • 3-hydroxy-5alpha-pregnan-20-one (CHEBI:11909 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030173 )
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
Polarizability38.72 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
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-0129000000-90e5fcb36022dd1ba688Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0396000000-4c39fe7ccd8e0c86e179Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2490000000-7ac55935cc0d4da95860Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-fa09e69c9c0b6736d2e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0069000000-d1d57e3e1a99da4ed11fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-1193000000-44d1597a59ac11f16a41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0029000000-87d0f95f5dbd34be3481Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i0v-1985000000-41959912f77ca2ce0a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-6950000000-e08ac95bf48862f7a6a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0019000000-2f80b71569ae462f9c19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0039000000-8ffa894a38bb04888d3bSpectrum
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 IDDB12972
HMDB IDHMDB0001455
FooDB IDFDB022634
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83761
ChEBI ID11909
PubChem Compound ID92787
Kegg Compound IDC15484
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kametani, Tetsuji; Suzuki, Koji; Nemoto, Hideo. Efficient synthesis of a pregnane-type steroid. Total synthesis of (+)-5a-dihydropregnenolone [(+)-3b-hydroxy-5a-pregnan-20-one]. Journal of the Chemical Society, Perkin Transactions 1. 1980, p.2805-2807
2. Kametani, Tetsuji; Suzuki, Koji; Nemoto, Hideo. Efficient synthesis of a pregnane-type steroid. Total synthesis of (+)-5a-dihydropregnenolone [(+)-3b-hydroxy-5a-pregnan-20-one]. Journal of the Chemical Society, Perkin Transactions 1. 1980, p.2805-2807
3. Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7.
4. Debatin T, Barbosa AD: Effect of isopregnanolone on rapid tolerance to the anxiolytic effect of ethanol. Rev Bras Psiquiatr. 2006 Mar;28(1):18-23. Epub 2006 Mar 24.