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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-22 23:27:55 UTC
HMDB IDHMDB0000774
Secondary Accession Numbers
  • HMDB00774
Metabolite Identification
Common NamePregnenolone sulfate
DescriptionPregnenolone sulfate belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Pregnenolone sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752155
Synonyms
ValueSource
Pregnenolone sulfuric acidGenerator
Pregnenolone sulphateGenerator
Pregnenolone sulphuric acidGenerator
5-Pregnen-3b-sulfate-20-oneHMDB
5-Pregnen-3b-sulphate-20-oneHMDB
Pregn-5-en-20-on-3b-yl sulfurateHMDB
Pregn-5-en-20-on-3b-yl sulfuric acidHMDB
Pregn-5-en-20-one-3b-yl sulfateHMDB
Pregn-5-en-20-one-3b-yl sulphateHMDB
Pregnenolone 3-sulfateHMDB
Pregnenolone 3-sulphateHMDB
Pregnenolone 3b-sulfateHMDB
Pregnenolone 3b-sulphateHMDB
Pregnenolone hydrogen sulfateHMDB
Pregnenolone hydrogen sulphateHMDB
Pregnenolone monosulfateHMDB
Pregnenolone monosulphateHMDB
[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonateHMDB
[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonateHMDB
[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonic acidHMDB
Chemical FormulaC21H32O5S
Average Molecular Weight396.541
Monoisotopic Molecular Weight396.197044824
IUPAC Name[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Name[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid
CAS Registry Number1247-64-9
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[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-OZIWPBGVSA-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 DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
Polarizability43.84 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, Positivesplash10-015c-1069000000-98638a32c64bd13693bbSpectrum
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
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Ovary
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.13 +/- 0.06 uMAdult (>18 years old)BothNormal
    • Tietz NW eds. Cli...
details
BloodDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    BloodDetected but not Quantified Adult (>18 years old)Male
    Schizophrenia
    details
    BloodDetected but not Quantified Adult (>18 years old)Female
    Schizophrenia
    details
    Associated Disorders and Diseases
    Disease References
    Schizophrenia
    1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB022235
    KNApSAcK IDNot Available
    Chemspider ID17216005
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG ID2705327
    Wikipedia LinkPregnenolone sulfate
    METLIN ID5740
    PubChem Compound20845972
    PDB IDNot Available
    ChEBI IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceKillinger, Donald W.; Solomon, Samuel. Synthesis of pregnenolone sulfate, dehydroisoandrosterone sulfate, 17a-hydroxypregnenolone sulfate, and pregn-5-enetriol by the normal human adrenal gland. Journal of Clinical Endocrinology and Metabolism (1965), 25(2), 290-3.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Horak M, Vlcek K, Chodounska H, Vyklicky L Jr: Subtype-dependence of N-methyl-D-aspartate receptor modulation by pregnenolone sulfate. Neuroscience. 2006;137(1):93-102. Epub 2005 Oct 28. [PubMed:16257494 ]
    2. Havlikova H, Hill M, Hampl R, Starka L: Sex- and age-related changes in epitestosterone in relation to pregnenolone sulfate and testosterone in normal subjects. J Clin Endocrinol Metab. 2002 May;87(5):2225-31. [PubMed:11994368 ]
    3. Bicikova M, Klak J, Hill M, Zizka Z, Hampl R, Calda P: Two neuroactive steroids in midpregnancy as measured in maternal and fetal sera and in amniotic fluid. Steroids. 2002 Apr;67(5):399-402. [PubMed:11958797 ]
    4. Kamiya T, Yasui T, Yokomori H, Nakamoto H, Maruyama T, Suzuki O, Ookawa H, Kiryu Y, Yasumura K, Kakumoto Y, et al.: [2 surgically treated cases of adrenocortical carcinoma producing steroid hormones without endocrinological symptoms--case report and a review of cases in the Japanese literature]. Gan No Rinsho. 1988 Jan;34(1):97-106. [PubMed:2963158 ]