Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 06:17:21 UTC
Update Date2022-03-07 03:17:59 UTC
HMDB IDHMDB0062782
Secondary Accession Numbers
  • HMDB62782
Metabolite Identification
Common NamePregnanolone
DescriptionPregnanolone, also known as eltanolone or 3alpha-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. Pregnanolone is considered to be practically insoluble (in water) and basic. Pregnanolone is an endogenous inhibitory neurosteroid that is produced in the body from progesterone. It is closely related to allopregnanolone, which has similar properties (Wikipedia ).
Structure
Data?1574096874
Synonyms
ValueSource
(3alpha,5beta)-3-Hydroxypregnan-20-oneChEBI
3alpha-Hydroxy-5beta-pregnane-20-oneChEBI
EltanolonaChEBI
EltanolonumChEBI
Pregnan-3alpha-ol-20-oneChEBI
PregnanoloneChEBI
(3a,5b)-3-Hydroxypregnan-20-oneGenerator
(3Α,5β)-3-hydroxypregnan-20-oneGenerator
3a-Hydroxy-5b-pregnane-20-oneGenerator
3Α-hydroxy-5β-pregnane-20-oneGenerator
Pregnan-3a-ol-20-oneGenerator
Pregnan-3α-ol-20-oneGenerator
Pregnanolone, (3alpha, 5beta, 17-alpha)-isomerMeSH
alpha-Hydroxy-5 alpha-pregnan-20-one, 3MeSH
3 alpha Hydroxy 5 beta pregnan 20 oneMeSH
3-Hydroxypregnan-20-oneMeSH
3 alpha, 5 beta-TetrahydroprogesteroneMeSH
Pregnanolone, (3alpha)-isomerMeSH
3 alpha, 5 beta TetrahydroprogesteroneMeSH
3 Hydroxypregnan 20 oneMeSH
3 alpha-Hydroxy-5 beta-pregnan-20-oneMeSH
Pregnanolone, (3alpha,5beta)-isomerMeSH
beta-Pregnan-20-one, 3 alpha-hydroxy-5MeSH
EltanoloneChEBI
3a-Hydroxy-5b-pregnan-20-oneGenerator
3Α-hydroxy-5β-pregnan-20-oneGenerator
3-Deoxo-3alpha-hydroxy-5beta-dihydroprogesteroneHMDB
3-Deoxo-3α-hydroxy-5β-dihydroprogesteroneHMDB
3alpha,5beta-PregnanoloneHMDB
3alpha,5beta-TetrahydroprogesteroneHMDB
3alpha-Hydroxy-20-oxo-5beta-pregnaneHMDB
3alpha-Hydroxy-5beta,17beta-pregnan-20-oneHMDB
3alpha-Hydroxy-5beta-pregnan-20-oneHMDB
3alpha-Hydroxy-5beta-tetrahydroprogesteroneHMDB
3α,5β-PregnanoloneHMDB
3α,5β-TetrahydroprogesteroneHMDB
3α-Hydroxy-20-oxo-5β-pregnaneHMDB
3α-Hydroxy-5β,17β-pregnan-20-oneHMDB
3α-Hydroxy-5β-tetrahydroprogesteroneHMDB
5beta-Pregnan-3alpha-ol-20-oneHMDB
5beta-Pregnane-3alpha-ol-20-oneHMDB
5β-Pregnan-3α-ol-20-oneHMDB
5β-Pregnane-3α-ol-20-oneHMDB
Chemical FormulaC21H34O2
Average Molecular Weight318.501
Monoisotopic Molecular Weight318.255880335
IUPAC Name1-[(1S,2S,5R,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,5R,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 Number128-20-1
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-YZRLXODZSA-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-alpha-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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0014 g/lALOGPS
LogP4.28ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability38.37 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]+174.58531661259
DarkChem[M-H]-171.54231661259
DeepCCS[M-2H]-207.59830932474
DeepCCS[M+Na]+181.92430932474
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
Pregnanolone[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
Pregnanolone[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
Pregnanolone[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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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
Pregnanolone,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 - Pregnanolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb082017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pregnanolone GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pregnanolone 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 - Pregnanolone 10V, Positive-QTOFsplash10-0uxr-0129000000-90e5fcb36022dd1ba6882017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 20V, Positive-QTOFsplash10-0uxr-0396000000-4c39fe7ccd8e0c86e1792017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 40V, Positive-QTOFsplash10-0006-2490000000-7ac55935cc0d4da958602017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 10V, Negative-QTOFsplash10-014i-0029000000-fa09e69c9c0b6736d2e72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 20V, Negative-QTOFsplash10-014i-0069000000-d1d57e3e1a99da4ed11f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 40V, Negative-QTOFsplash10-0zg0-1193000000-44d1597a59ac11f16a412017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 10V, Positive-QTOFsplash10-0gb9-0019000000-5b53b3ba37ccafca449f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 20V, Positive-QTOFsplash10-0lgi-1797000000-c11629ffa10cac4be1182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 40V, Positive-QTOFsplash10-0a4m-8910000000-2813a600e98ff59972752021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 10V, Negative-QTOFsplash10-014i-0009000000-bbaa566ea695ae62f84e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 20V, Negative-QTOFsplash10-014i-0029000000-ac1c6a15538469151b6c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnanolone 40V, Negative-QTOFsplash10-00ks-0093000000-db70f670eb2440b743f92021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12308
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID29132
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPregnanolone
METLIN IDNot Available
PubChem Compound31402
PDB IDNot Available
ChEBI ID1712
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.