17-Hydroxypregnenolone sulfate (CHEM022502)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:37:43 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022502
Identification
Common Name17-Hydroxypregnenolone sulfate
ClassSmall Molecule
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 [HMDB]
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass412.540 g/mol
Monoisotopic Mass412.192 g/mol
CAS Registry Number2477-77-2
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.15 m³·mol⁻¹ChemAxon
Polarizability44.61 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-3049000000-9c6e65ea67163f53af17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01bc-3017900000-c6ea7d6f70ffeb89f234Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0029700000-274d7e95447f04a41dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0069000000-742b7c9d057f124dec29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00p1-1791000000-fa71d6406119fb6cb914Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0004900000-bb7eb444a33e79f1bc5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ar-1039100000-01f26facb55859a32471Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00m0-6079000000-0a468b106febe627e93eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0008900000-8cd42f124dd146d329b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0394000000-7d3d1ee7f1377af66db4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-7694000000-5950827a4b89bce33690Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001900000-124239a49ac3287d9a2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1008900000-ceb13132aa142a1414f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr2-6009000000-bd6192774ade965b0af4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000416
FooDB IDFDB022032
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5405
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID134824
ChEBI IDNot Available
PubChem Compound ID152971
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gasparini, Francis J.; Hochberg, Richard B.; Lieberman, Seymour. Biosynthesis of steroid sulfates by the boar testes. Biochemistry (1976), 15(18), 3969-75.
2. 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.
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.
4. Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17.