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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-08-06 14:56:15 UTC
Update Date2021-09-14 15:19:03 UTC
HMDB IDHMDB0006759
Secondary Accession Numbers
  • HMDB06759
Metabolite Identification
Common Name3a-Hydroxy-5b-pregnane-20-one
Description3alpha-Hydroxy-5beta-pregnane-20-one is an intermediate in C21-Steroid hormone metabolism. 3alpha-Hydroxy-5beta-pregnane-20-one is converted from 5beta-Pregnane-3,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). It is then converted to Pregnanediol via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53).
Structure
Data?1582752404
Synonyms
ValueSource
3alpha-Hydroxy-5beta-pregnane-20-oneHMDB
Chemical FormulaC21H34O2
Average Molecular Weight318.4935
Monoisotopic Molecular Weight318.255880332
IUPAC Name1-[(2S,5R,7R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one
Traditional Namepregnanolone
CAS Registry NumberNot Available
SMILES
[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2
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-KCZNCWLVSA-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

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
logP10(4.28) g/LALOGPS
logP10(3.99) g/LChemAxon
logS10(-5.4) g/LALOGPS
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
Polarizability38.36 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]+173.03131661259
DarkChem[M-H]-172.86331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3a-Hydroxy-5b-pregnane-20-one[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C22278.9Standard polar33892256
3a-Hydroxy-5b-pregnane-20-one[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C22660.8Standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C22834.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3a-Hydroxy-5b-pregnane-20-one,1TMS,isomer #1CC(=O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C2742.2Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@]12C2764.7Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@@]21C2743.4Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C2754.3Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C2748.8Standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C3115.8Standard polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C2718.9Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C2736.5Standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C3208.2Standard polar33892256
3a-Hydroxy-5b-pregnane-20-one,1TBDMS,isomer #1CC(=O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C2989.8Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@]12C3021.5Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@@]21C3010.0Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3226.2Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3256.6Standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C3358.5Standard polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3211.9Semi standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3240.8Standard non polar33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C3424.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-11du-0292000000-d5c96280786507060adf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one GC-MS (1 TMS) - 70eV, Positivesplash10-01t9-1109000000-2c47b5bb98f0821612012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a-Hydroxy-5b-pregnane-20-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 - 3a-Hydroxy-5b-pregnane-20-one 10V, Positive-QTOFsplash10-0uxr-0019000000-82b5328b4643c0421b0d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Positive-QTOFsplash10-0uxr-1496000000-6fd25d5861771fb104b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Positive-QTOFsplash10-002o-2490000000-ba6e2bc4d584ea3d3a4b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 10V, Negative-QTOFsplash10-014i-0029000000-826f869c8c8e3739b52e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Negative-QTOFsplash10-014i-0059000000-699658e7c96cdaee62e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Negative-QTOFsplash10-0zmr-1092000000-9cb4a247b808ab6f5c272017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 10V, Negative-QTOFsplash10-014i-0009000000-bbaa566ea695ae62f84e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Negative-QTOFsplash10-014i-0019000000-b27ed891ac6811eab39d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Negative-QTOFsplash10-014i-0039000000-ee44f8ffc9f4d431f1b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 10V, Positive-QTOFsplash10-0uxr-0039000000-5b11ff3658bc22f27d0a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Positive-QTOFsplash10-0j6v-0984000000-16637ba86fccb8e48e172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Positive-QTOFsplash10-0a4m-6950000000-17eb447f04784923dcfe2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00016 +/- 0.00018 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00052 +/- 0.00042 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024063
KNApSAcK IDNot Available
Chemspider ID23141070
KEGG Compound IDC05480
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779614
PDB IDNot Available
ChEBI ID88767
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 ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
3a-Hydroxy-5b-pregnane-20-one + NAD → 5a-Pregnane-3,20-dione + NADH + Hydrogen Iondetails
3a-Hydroxy-5b-pregnane-20-one + NADP → 5a-Pregnane-3,20-dione + NADPH + Hydrogen Iondetails