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Record Information
Version3.6
Creation Date2013-05-17 00:58:23 UTC
Update Date2016-02-11 08:04:44 UTC
HMDB IDHMDB60382
Secondary Accession NumbersNone
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 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=1/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+/s2
InChI KeyInChIKey=DIJBBUIOWGGQOP-VUCNLTLINA-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
StatusExpected but not Quantified
Origin
  • Drug or steroid metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
Polarizability43.8 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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 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
NuGOwiki LinkHMDB60382
Metagene LinkHMDB60382
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, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [21447597 ]

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