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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:18:43 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-Hydroxy-pregnenolone sulfateHMDB
17-Hydroxy-pregnenolone sulphateHMDB
17-Hydroxypregnenolone 3-sulfateHMDB
17-Hydroxypregnenolone 3-sulphateHMDB
17-Hydroxypregnenolone sulphateHMDB
17alpha-Hydroxypregnenolone sulfateHMDB
17alpha-Hydroxypregnenolone sulphateHMDB
17b-Hydroxypregnenolone 3-sulfateHMDB
17b-Hydroxypregnenolone 3-sulphateHMDB
17 alpha-Hydroxypregnenolone sulfateMeSH
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
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 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
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 (predicted from logP)
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 Solubility0.02 mg/mLALOGPS
logP0.37ALOGPS
logP2.89ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.15 m3·mol-1ChemAxon
Polarizability44.61 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
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adrenal Cortex
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (1.56-5.03) uMInfant (0-1 year old)BothNormal 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 IDDBMET00500
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022032
    KNApSAcK IDNot Available
    Chemspider ID134824
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0000416
    METLIN ID5405
    PubChem Compound152971
    PDB IDNot Available
    ChEBI 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 ]