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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:21 UTC
HMDB IDHMDB00774
Secondary Accession NumbersNone
Metabolite Identification
Common NamePregnenolone sulfate
DescriptionPregnenolone sulfate, a neurosteroid, is a metabolite of Pregnenolone. It is found in the brain and central nervous system.
Structure
Thumb
Synonyms
ValueSource
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
Pregnenolone sulphateHMDB
Chemical FormulaC21H32O5S
Average Molecular Weight396.541
Monoisotopic Molecular Weight396.197044824
IUPAC Name[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Name[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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 KeyInChIKey=DIJBBUIOWGGQOP-OZIWPBGVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 3-sulfated steroid
  • Sulfated steroid skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • Oxosteroid
  • Delta-5-steroid
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug or steroid metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.75 m3·mol-1ChemAxon
Polarizability43.79 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Gonads
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.13 +/- 0.06 uMAdult (>18 years old)BothNormal
    • Tietz NW eds. Cli...
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00511
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022235
KNApSAcK IDNot Available
Chemspider ID17216005
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2705327
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00774
Metagene LinkHMDB00774
METLIN ID5740
PubChem Compound20845972
PDB IDNot Available
ChEBI 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. 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. [11994368 ]
  2. 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. [16257494 ]
  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. [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. [2963158 ]