Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:57:00 UTC
Update Date2021-09-26 22:54:38 UTC
HMDB IDHMDB0245902
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxypregnan-20-one
Description1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethan-1-one 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. Based on a literature review very few articles have been published on 1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethan-1-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-hydroxypregnan-20-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Hydroxypregnan-20-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
3 alpha, 5 beta-TetrahydroprogesteroneMeSH, HMDB
EpipregnanoloneMeSH, HMDB
Pregnan 3alpha ol 20 oneMeSH, HMDB
Pregnanolone, (3alpha, 5beta, 17-alpha)-isomerMeSH, HMDB
Pregnanolone, (3beta)-isomerMeSH, HMDB
Pregnanolone, (3beta, 5alpha, 17alpha)-isomerMeSH, HMDB
alpha-Hydroxy-5 alpha-pregnan-20-one, 3MeSH, HMDB
alpha-Hydroxy-5 beta-pregnan-20-one, 3MeSH, HMDB
alpha-Pregnan-20-one, 3 alpha-hydroxy-5MeSH, HMDB
beta-Ol-20-one, allopregnan-3MeSH, HMDB
3 alpha, 5 beta TetrahydroprogesteroneMeSH, HMDB
3 alpha-Hydroxy-5 alpha-pregnan-20-oneMeSH, HMDB
3 alpha-Hydroxy-5 beta-pregnan-20-oneMeSH, HMDB
Pregnanolone, (3alpha,5beta)-isomerMeSH, HMDB
Pregnanolone, (3beta, 5beta, 17alpha)-isomerMeSH, HMDB
Pregnanolone, (3beta, 5beta,14beta)-isomerMeSH, HMDB
3 Hydroxypregnan 20 oneMeSH, HMDB
3 alpha Hydroxy 5 alpha pregnan 20 oneMeSH, HMDB
3-Hydroxypregnan-20-oneMeSH
3beta Hydroxy 5alpha pregnan 20 oneMeSH, HMDB
3beta-Hydroxy-5alpha-pregnan-20-oneMeSH, HMDB
Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomerMeSH, HMDB
Pregnanolone, (5alpha)-isomerMeSH, HMDB
3 alpha Hydroxy 5 beta pregnan 20 oneMeSH, HMDB
Allopregnan 3 beta ol 20 oneMeSH, HMDB
Allopregnan-3 beta-ol-20-oneMeSH, HMDB
EltanoloneMeSH, HMDB
Pregnan-3alpha-ol-20-oneMeSH, HMDB
PregnanoloneMeSH, HMDB
Pregnanolone, (3alpha)-isomerMeSH, HMDB
Pregnanolone, (3alpha,5alpha)-isomerMeSH, HMDB
Pregnanolone, (3beta, 5alpha)-isomerMeSH, HMDB
Pregnanolone, (3beta, 5beta)-isomerMeSH, HMDB
SepranoloneMeSH, HMDB
beta-Pregnan-20-one, 3 alpha-hydroxy-5MeSH, HMDB
Chemical FormulaC21H34O2
Average Molecular Weight318.501
Monoisotopic Molecular Weight318.255880335
IUPAC Name1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}ethan-1-one
Traditional Name1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}ethanone
CAS Registry NumberNot Available
SMILES
CC(=O)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C
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
InChI KeyAURFZBICLPNKBZ-UHFFFAOYSA-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
  • Oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
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
Polarizability38.47 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
DeepCCS[M-2H]-207.71330932474
DeepCCS[M+Na]+182.9430932474
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

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxypregnan-20-one,1TMS,isomer #1CC(=O)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C2815.5Semi standard non polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #1CC(=O)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C2663.5Standard non polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #1CC(=O)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3042.8Standard polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2760.7Semi standard non polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2657.1Standard non polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3090.5Standard polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #3C=C(O[Si](C)(C)C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2763.7Semi standard non polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #3C=C(O[Si](C)(C)C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2653.8Standard non polar33892256
3-Hydroxypregnan-20-one,1TMS,isomer #3C=C(O[Si](C)(C)C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3170.6Standard polar33892256
3-Hydroxypregnan-20-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C2776.5Semi standard non polar33892256
3-Hydroxypregnan-20-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C2740.2Standard non polar33892256
3-Hydroxypregnan-20-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3099.2Standard polar33892256
3-Hydroxypregnan-20-one,2TMS,isomer #2C=C(O[Si](C)(C)C)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C2730.9Semi standard non polar33892256
3-Hydroxypregnan-20-one,2TMS,isomer #2C=C(O[Si](C)(C)C)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C2718.9Standard non polar33892256
3-Hydroxypregnan-20-one,2TMS,isomer #2C=C(O[Si](C)(C)C)C1CCC2C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3170.8Standard polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #1CC(=O)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3037.3Semi standard non polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #1CC(=O)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C2950.2Standard non polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #1CC(=O)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3199.7Standard polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3017.3Semi standard non polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2922.3Standard non polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3256.8Standard polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3022.3Semi standard non polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C2916.2Standard non polar33892256
3-Hydroxypregnan-20-one,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4CC(O)CCC4(C)C3CCC12C3323.5Standard polar33892256
3-Hydroxypregnan-20-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3261.7Semi standard non polar33892256
3-Hydroxypregnan-20-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3258.4Standard non polar33892256
3-Hydroxypregnan-20-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3344.1Standard polar33892256
3-Hydroxypregnan-20-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3235.1Semi standard non polar33892256
3-Hydroxypregnan-20-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3236.0Standard non polar33892256
3-Hydroxypregnan-20-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1CCC2C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C3392.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethan-1-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0m0g-0292000000-47240ed280e9ee2d7e772018-04-09Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethan-1-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}ethan-1-one 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 - 3-Hydroxypregnan-20-one 10V, Positive-QTOFsplash10-0uxr-0019000000-82b5328b4643c0421b0d2018-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 20V, Positive-QTOFsplash10-0uxr-1496000000-6fd25d5861771fb104b72018-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 40V, Positive-QTOFsplash10-002o-2490000000-ba6e2bc4d584ea3d3a4b2018-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 10V, Negative-QTOFsplash10-014i-0029000000-826f869c8c8e3739b52e2018-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 20V, Negative-QTOFsplash10-014i-0059000000-699658e7c96cdaee62e82018-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 40V, Negative-QTOFsplash10-0zmr-1092000000-19955e9b1f2b26db24252018-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 10V, Positive-QTOFsplash10-0gb9-0029000000-47fe23f7ec61a49ff3b42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 20V, Positive-QTOFsplash10-0lgi-1977000000-ca09c035d2c8e0334fee2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 40V, Positive-QTOFsplash10-0a4l-4900000000-c6027dbdc77ecca6ec272021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 10V, Negative-QTOFsplash10-014i-0009000000-bbaa566ea695ae62f84e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 20V, Negative-QTOFsplash10-014i-0039000000-f2a2e238922710f55dea2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypregnan-20-one 40V, Negative-QTOFsplash10-00kr-0094000000-5f67c11ca7f10d1692ff2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID230963
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound262961
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]