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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:58:23 UTC
Update Date2019-07-23 07:14:13 UTC
HMDB IDHMDB0060382
Secondary Accession Numbers
  • HMDB60382
Metabolite Identification
Common Name3beta-Hydroxypregn-5-en-20-one sulfate
Description3beta-Hydroxypregn-5-en-20-one sulfate is a metabolite of pregnenolone. Pregnenolone, also known as 3α,5β-tetrahydroprogesterone (3α,5β-THP), is an endogenous steroid hormone involved in the steroidogenesis of progestogens, mineralocorticoids, glucocorticoids, androgens, and estrogens, as well as the neuroactive steroids. As such it is a prohormone, though it also has biological effects of its own, behaving namely as a neuroactive steroid in its own right with potent anxiolytic effects. (Wikipedia)
Structure
Data?1563866053
Synonyms
ValueSource
(3beta)-3-(Sulfooxy)pregn-5-en-20-oneChEBI
5-Pregnen-3beta-ol-20-one sulfateChEBI
Pregnenolone sulfateKegg
(3b)-3-(Sulfooxy)pregn-5-en-20-oneGenerator
(3b)-3-(Sulphooxy)pregn-5-en-20-oneGenerator
(3beta)-3-(Sulphooxy)pregn-5-en-20-oneGenerator
(3Β)-3-(sulfooxy)pregn-5-en-20-oneGenerator
(3Β)-3-(sulphooxy)pregn-5-en-20-oneGenerator
5-Pregnen-3b-ol-20-one sulfateGenerator
5-Pregnen-3b-ol-20-one sulfuric acidGenerator
5-Pregnen-3b-ol-20-one sulphateGenerator
5-Pregnen-3b-ol-20-one sulphuric acidGenerator
5-Pregnen-3beta-ol-20-one sulfuric acidGenerator
5-Pregnen-3beta-ol-20-one sulphateGenerator
5-Pregnen-3beta-ol-20-one sulphuric acidGenerator
5-Pregnen-3β-ol-20-one sulfateGenerator
5-Pregnen-3β-ol-20-one sulfuric acidGenerator
5-Pregnen-3β-ol-20-one sulphateGenerator
5-Pregnen-3β-ol-20-one sulphuric acidGenerator
Pregnenolone sulfuric acidGenerator
Pregnenolone sulphateGenerator
Pregnenolone sulphuric acidGenerator
3b-Hydroxypregn-5-en-20-one sulfateGenerator
3b-Hydroxypregn-5-en-20-one sulfuric acidGenerator
3b-Hydroxypregn-5-en-20-one sulphateGenerator
3b-Hydroxypregn-5-en-20-one sulphuric acidGenerator
3beta-Hydroxypregn-5-en-20-one sulfuric acidGenerator
3beta-Hydroxypregn-5-en-20-one sulphateGenerator
3beta-Hydroxypregn-5-en-20-one sulphuric acidGenerator
3Β-hydroxypregn-5-en-20-one sulfateGenerator
3Β-hydroxypregn-5-en-20-one sulfuric acidGenerator
3Β-hydroxypregn-5-en-20-one sulphateGenerator
3Β-hydroxypregn-5-en-20-one sulphuric acidGenerator
5-Pregnen-3 beta-ol-20-one sulfateHMDB
Pregnenolone sulfate, (3alpha)-isomerHMDB
Pregnenolone sulfate, sodium salt, (3beta)-isomerHMDB
Chemical FormulaC21H32O5S
Average Molecular Weight396.541
Monoisotopic Molecular Weight396.197044824
IUPAC Name[(1S,2R,5S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Namepregnenolone sulfate
CAS Registry NumberNot Available
SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OS(O)(=O)=O
InChI Identifier
InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15-,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyDIJBBUIOWGGQOP-QGVNFLHTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSulfated steroids
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • 20-oxosteroid
  • Pregnane-skeleton
  • Oxosteroid
  • Delta-5-steroid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP0.98ALOGPS
logP3.64ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.75 m³·mol⁻¹ChemAxon
Polarizability43.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fzc-1159000000-acf34658da399992de80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0039000000-c29e72af13a8b1df901aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0092000000-48af0541d95515a42ecaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-5193000000-d981003b06fdf18508e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-2cac349b15d130782aefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1039000000-f63d28f7bec5ec72f437Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-6093000000-3f7db3bec91ec381b060Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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 IDNot Available
      KEGG Compound IDC18044
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkPregnenolone sulfate
      METLIN IDNot Available
      PubChem Compound105074
      PDB IDNot Available
      ChEBI ID35420
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
      2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
      3. 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 ]
      4. 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 ]
      5. 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 ]
      6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

      Enzymes

      General function:
      Involved in sulfotransferase activity
      Specific function:
      Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
      Gene Name:
      SULT2B1
      Uniprot ID:
      O00204
      Molecular weight:
      39598.595
      Reactions
      Pregnenolone + Phosphoadenosine phosphosulfate → 3beta-Hydroxypregn-5-en-20-one sulfate + Adenosine 3',5'-diphosphatedetails
      General function:
      Involved in catalytic activity
      Specific function:
      Conversion of sulfated steroid precursors to estrogens during pregnancy.
      Gene Name:
      STS
      Uniprot ID:
      P08842
      Molecular weight:
      65491.72
      Reactions
      Pregnenolone + Oat gum → 3beta-Hydroxypregn-5-en-20-one sulfate + Waterdetails