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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-16 15:25:22 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001471
Secondary Accession Numbers
  • HMDB01471
Metabolite Identification
Common NameEpipregnanolone
DescriptionEpipregnanolone, also known as 3beta-hydroxy-5beta-pregnan-20-one, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogens, and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, epipregnanolone is considered to be a steroid lipid molecule. Epipregnanolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Epipregnanolone is a pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties. It is a substrate of the enzyme 3beta-hydroxy-5beta-steroid dehydrogenase (EC 1.1.1.277).
Structure
Data?1582752203
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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.12231661259
DarkChem[M-H]-173.33731661259
AllCCS[M+H]+183.35832859911
AllCCS[M-H]-187.19132859911
DeepCCS[M-2H]-205.73430932474
DeepCCS[M+Na]+179.93830932474
AllCCS[M+H]+183.432859911
AllCCS[M+H-H2O]+180.532859911
AllCCS[M+NH4]+186.032859911
AllCCS[M+Na]+186.832859911
AllCCS[M-H]-187.232859911
AllCCS[M+Na-2H]-187.732859911
AllCCS[M+HCOO]-188.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epipregnanolone[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)=O2222.5Standard polar33892256
Epipregnanolone[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)=O2649.9Standard non polar33892256
Epipregnanolone[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)=O2869.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epipregnanolone,1TMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2738.7Semi standard non polar33892256
Epipregnanolone,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2783.9Semi standard non polar33892256
Epipregnanolone,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2734.6Semi standard non polar33892256
Epipregnanolone,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2787.6Semi standard non polar33892256
Epipregnanolone,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2777.0Standard non polar33892256
Epipregnanolone,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3133.8Standard polar33892256
Epipregnanolone,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2760.9Semi standard non polar33892256
Epipregnanolone,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2765.2Standard non polar33892256
Epipregnanolone,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3230.8Standard polar33892256
Epipregnanolone,1TBDMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2985.7Semi standard non polar33892256
Epipregnanolone,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C3032.5Semi standard non polar33892256
Epipregnanolone,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2995.8Semi standard non polar33892256
Epipregnanolone,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3282.4Semi standard non polar33892256
Epipregnanolone,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3254.0Standard non polar33892256
Epipregnanolone,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3369.8Standard polar33892256
Epipregnanolone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3288.7Semi standard non polar33892256
Epipregnanolone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3256.2Standard non polar33892256
Epipregnanolone,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3436.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Epipregnanolone GC-EI-TOF (Non-derivatized)splash10-0udr-4900000000-39156fa655392898752f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epipregnanolone GC-EI-TOF (Non-derivatized)splash10-0udr-4900000000-39156fa655392898752f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epipregnanolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb082017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epipregnanolone GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epipregnanolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 10V, Positive-QTOFsplash10-0uxr-0019000000-82b5328b4643c0421b0d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 20V, Positive-QTOFsplash10-0uxr-1496000000-6fd25d5861771fb104b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 40V, Positive-QTOFsplash10-002o-2490000000-ba6e2bc4d584ea3d3a4b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 10V, Negative-QTOFsplash10-014i-0029000000-826f869c8c8e3739b52e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 20V, Negative-QTOFsplash10-014i-0059000000-699658e7c96cdaee62e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 40V, Negative-QTOFsplash10-0zmr-1092000000-19955e9b1f2b26db24252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 10V, Negative-QTOFsplash10-014i-0009000000-bbaa566ea695ae62f84e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 20V, Negative-QTOFsplash10-014i-0029000000-ac1c6a15538469151b6c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 40V, Negative-QTOFsplash10-00ks-0093000000-db70f670eb2440b743f92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 10V, Positive-QTOFsplash10-0gb9-0019000000-5b53b3ba37ccafca449f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 20V, Positive-QTOFsplash10-0lgi-1797000000-c11629ffa10cac4be1182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epipregnanolone 40V, Positive-QTOFsplash10-0a4m-8910000000-2813a600e98ff59972752021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.003 +/- 0.0018 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.00034 +/- 0.00011 uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.003 +/- 0.001 uMAdult (>18 years old)Female
Prepartum depression
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Prepartum depression
  1. 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. [PubMed:11739473 ]
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHalpern, Otto. Pregnenolones and androstenolones. U.S. (1969), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:11739473 ]