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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:58:23 UTC
Update Date2017-12-07 16:52:45 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
Thumb
Synonyms
ValueSource
(3beta)-3-(Sulfooxy)pregn-5-en-20-oneChEBI
5-Pregnen-3beta-ol-20-one sulfateChEBI
(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
Pregnenolone sulfuric acidGenerator
Pregnenolone sulphateGenerator
Pregnenolone sulphuric acidGenerator
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
5-Pregnen-3 beta-ol-20-one sulfateMeSH
Pregnenolone sulfate, (3alpha)-isomerMeSH
Pregnenolone sulfate, sodium salt, (3beta)-isomerMeSH
Chemical FormulaC21H32O5S
Average Molecular Weight396.541
Monoisotopic Molecular Weight396.197044824
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
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
DescriptionThis compound belongs to the class of chemical entities known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassSteroids and steroid derivatives
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

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Cellular process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fzc-1159000000-acf34658da399992de80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0039000000-c29e72af13a8b1df901aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0092000000-48af0541d95515a42ecaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-5193000000-d981003b06fdf18508e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-2cac349b15d130782aefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-1039000000-f63d28f7bec5ec72f437View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-6093000000-3f7db3bec91ec381b060View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
      DrugBank Metabolite IDDBMET00654
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID94802
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound105074
      PDB IDNot Available
      ChEBI ID35420
      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