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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-16 15:13:08 UTC
Update Date2022-03-07 02:49:10 UTC
HMDB IDHMDB0001455
Secondary Accession Numbers
  • HMDB01455
Metabolite Identification
Common NameAlloepipregnanolone
DescriptionAlloepipregnanolone, also known as eltanolone, 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, alloepipregnanolone is considered to be a steroid. Based on a literature review very few articles have been published on Alloepipregnanolone.
Structure
Data?1582752203
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 Weight318.4935
Monoisotopic Molecular Weight318.255880332
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
CAS Registry Number516-55-2
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 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+/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 )
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194.5 °CNot 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
Polarizability38.72 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]+175.48831661259
DarkChem[M-H]-171.83831661259
AllCCS[M+H]+183.35832859911
AllCCS[M-H]-187.19132859911
DeepCCS[M-2H]-216.17630932474
DeepCCS[M+Na]+190.61130932474
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
Alloepipregnanolone[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@]12C2222.5Standard polar33892256
Alloepipregnanolone[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@]12C2649.9Standard non polar33892256
Alloepipregnanolone[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@]12C2869.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Alloepipregnanolone,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
Predicted GC-MSPredicted GC-MS Spectrum - Alloepipregnanolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb082017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alloepipregnanolone GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alloepipregnanolone 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 - Alloepipregnanolone 10V, Positive-QTOFsplash10-0uxr-0129000000-90e5fcb36022dd1ba6882017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Positive-QTOFsplash10-0uxr-0396000000-4c39fe7ccd8e0c86e1792017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Positive-QTOFsplash10-0006-2490000000-7ac55935cc0d4da958602017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 10V, Negative-QTOFsplash10-014i-0029000000-fa09e69c9c0b6736d2e72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Negative-QTOFsplash10-014i-0069000000-d1d57e3e1a99da4ed11f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Negative-QTOFsplash10-0zg0-1193000000-44d1597a59ac11f16a412017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 10V, Positive-QTOFsplash10-0gb9-0029000000-87d0f95f5dbd34be34812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Positive-QTOFsplash10-0i0v-1985000000-41959912f77ca2ce0a842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Positive-QTOFsplash10-052b-6950000000-e08ac95bf48862f7a6a82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 10V, Negative-QTOFsplash10-014i-0009000000-bbaa566ea695ae62f84e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Negative-QTOFsplash10-014i-0019000000-2f80b71569ae462f9c192021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Negative-QTOFsplash10-014i-0039000000-8ffa894a38bb04888d3b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0015 +/- 0.00062 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.00034 +/- 0.000075 uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.001 +/- 0.00075 uMAdult (>18 years old)FemalePremenstrual dysphoric disorder details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Schizophrenia
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Premenstrual dysphoric disorder
  1. Epperson CN, Haga K, Mason GF, Sellers E, Gueorguieva R, Zhang W, Weiss E, Rothman DL, Krystal JH: Cortical gamma-aminobutyric acid levels across the menstrual cycle in healthy women and those with premenstrual dysphoric disorder: a proton magnetic resonance spectroscopy study. Arch Gen Psychiatry. 2002 Sep;59(9):851-8. [PubMed:12215085 ]
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 IDDB12972
Phenol Explorer Compound IDNot Available
FooDB IDFDB022634
KNApSAcK IDNot Available
Chemspider ID83761
KEGG Compound IDC15484
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92787
PDB IDNot Available
ChEBI ID11909
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKametani, 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
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 ]
  2. 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. [PubMed:16612485 ]