3-β-hydroxyandrost-5-en-17-one 3-sulfate (PAMDB120555)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120555
Identification
Name: 3-β-hydroxyandrost-5-en-17-one 3-sulfate
Description:A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (3-beta)-3-(Sulfooxy)androst-5-en-17-one
  • 17-Ketoandrost-5-en-3beta-yl sulfate
  • 17-oxoandrost-5-en-3β-yl hydrogen sulphate
  • 3-O-Sulfodehydroepiandrosterone
  • 3beta-Hydroxyandrost-5-en-17-one 3-sulfate
  • 3beta-hydroxyandrost-5-en-17-one 3-sulfate
  • 3beta-Hydroxyandrost-5-en-17-one 3-sulfate
  • Androst-5-en-17-on-3beta-yl sulfuric acid
  • Dehydroepiandrosterone 3-sulfate
  • Dehydroepiandrosterone monosulfate
  • Dehydroepiandrosterone sulfate
  • Dehydroepiandrosterone sulphate
  • Dehydroisoandrosterone sulfate
  • Dehydroisoandrosterone-3-sulfate
  • DHEA sulfate
  • DHEA sulfate
  • DHEA-S
  • DHEAS
  • Prasterone sulfate
Chemical Formula: C19H29O5S
Average Molecular Weight: 369.495
Monoisotopic Molecular Weight: 370.1814
InChI Key: ZMITXKRGXGRMKS-QRIARFFBSA-M
InChI:InChI=1S/C19H30O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h12-16H,3-11H2,1-2H3,(H,21,22,23)/p-1/t12?,13-,14-,15-,16-,18-,19-/m0/s1
CAS number: 651-48-9
IUPAC Name:17-oxoandrost-5-en-3β-yl hydrogen sulfate
Traditional IUPAC Name: dehydroepiandrosterone sulfate
SMILES:CC24(CCC(CC(CC[CH]1([CH]3(CCC(=O)C(C)(CC[CH]12)3)))4)OS(=O)(=O)[O-])
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Steroids and steroid derivatives
Sub ClassSulfated steroids
Direct Parent Sulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • Androstane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Delta-5-steroid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfuric acid monoester
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular Framework Aliphatic homopolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0081 mg/mLALOGPS
logP0.49ALOGPS
logP3.42ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.65 m3·mol-1ChemAxon
Polarizability39.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Water + 3-β-hydroxyandrost-5-en-17-one 3-sulfate → Hydrogen ion + Sulfate + dehydroepiandrosterone
Pathways:
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
References
References:
  • Barrou Z, Charru P, Lidy C (1997)Dehydroepiandrosterone (DHEA) and aging. Archives of gerontology and geriatrics 24, Pubmed: 15374110
  • Sato H, Macchiarulo A, Thomas C, Gioiello A, Une M, Hofmann AF, Saladin R, Schoonjans K, Pellicciari R, Auwerx J (2008)Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies. Journal of medicinal chemistry 51, Pubmed: 18307294
  • Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Analytical chemistry 84, Pubmed: 22770225
  • Hemminki A, Niemi S, Hautoniemi L, Söderlund H, Takkinen K (1998)Fine tuning of an anti-testosterone antibody binding site by stepwise optimisation of the CDRs. Immunotechnology : an international journal of immunological engineering 4, Pubmed: 9661815
  • Leonardi R, Zhang YM, Yun MK, Zhou R, Zeng FY, Lin W, Cui J, Chen T, Rock CO, White SW, Jackowski S (2010)Modulation of pantothenate kinase 3 activity by small molecules that interact with the substrate/allosteric regulatory domain. Chemistry & biology 17, Pubmed: 20797618
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB01032
CHEBI1724
PUBCHEM25202700
LIGAND-CPDC04555