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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:01 UTC
HMDB IDHMDB0000416
Secondary Accession Numbers
  • HMDB00416
Metabolite Identification
Common Name17-Hydroxypregnenolone sulfate
Description17-Hydroxypregnenolone sulfate is a precursor steroid. 17-Hydroxypregnenolone is a C21 steroid that is obtained by hydroxylation of pregnenolone at the C17 alpha position.17-Hydroxypregnenolone is considered a prohormone in the formation of dehydroepiandrosterone (DHEA), itself a prohormone of the sex steroids (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
17-Hydroxypregnenolone sulfuric acidGenerator
17-Hydroxypregnenolone sulphateGenerator
17-Hydroxypregnenolone sulphuric acidGenerator
17-Hydroxy-pregnenolone sulfateHMDB
17-Hydroxy-pregnenolone sulphateHMDB
17-Hydroxypregnenolone 3-sulfateHMDB
17-Hydroxypregnenolone 3-sulphateHMDB
17alpha-Hydroxypregnenolone sulfateHMDB
17alpha-Hydroxypregnenolone sulphateHMDB
17b-Hydroxypregnenolone 3-sulfateHMDB
17b-Hydroxypregnenolone 3-sulphateHMDB
17 alpha-Hydroxypregnenolone sulfateHMDB
Chemical FormulaC21H32O6S
Average Molecular Weight412.54
Monoisotopic Molecular Weight412.191959446
IUPAC Name[(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Name17-hydroxypregnenolone sulfate
CAS Registry Number2477-77-2
SMILES
[H][C@@]12CC[C@](O)(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/C21H32O6S/c1-13(22)21(23)11-8-18-16-5-4-14-12-15(27-28(24,25)26)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23H,5-12H2,1-3H3,(H,24,25,26)/t15?,16-,17+,18+,19+,20+,21+/m1/s1
InChI KeyOMOKWYAQVYBHMG-QUPIPBJSSA-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
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic sulfuric acid or derivatives
  • Ketone
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Adrenal Cortex
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (1.56-5.03) uMInfant (0-1 year old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022032
KNApSAcK IDNot Available
Chemspider ID134824
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5405
PubChem Compound152971
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGasparini, Francis J.; Hochberg, Richard B.; Lieberman, Seymour. Biosynthesis of steroid sulfates by the boar testes. Biochemistry (1976), 15(18), 3969-75.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
  3. Shimozawa K, Saisho S, Yata J, Kambegawa A: Age-related changes in serum 17-hydroxypregnenolone and 17-hydroxypregnenolone sulfate concentrations in human infancy and childhood. Endocrinol Jpn. 1988 Apr;35(2):189-95. [PubMed:3208699 ]