5a-Dihydrotestosterone sulfate (CHEM022530)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:42 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022530
Identification
Common Name5a-Dihydrotestosterone sulfate
ClassSmall Molecule
Description5a-Dihydrotestosterone sulfate is a sulfate derivative of 5a-Dihydrotestosterone produced through phase II metabolism. 5a-dihydrotestosterone (DHT) is a steroid similar to testosterone and androstenedione, that belongs to a class called androgens. DHT is a C19 steroid and possesses androgenic activity. Androgen production takes place mainly in the Leydig cells of the testes. Androgens circulate in the blood bound to proteins, especially sex hormone binding globulin (SHBG) and albumin. A trace amount of these steroids circulate in the unbound form in the blood and are referred to as the free fractions. DHT has at least three times the binding affinity for SHBG than testosterone. About 70% of DHT is derived from peripheral conversion of testosterone in males, while most of the DHT is derived from androstenedione in females.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfateChEBI
5alpha-Dihydrotestosterone 17-sulfateChEBI
DHT-SulfateChEBI
DHT-SulphateChEBI
Dihydrotestosterone sulfateChEBI
Dihydrotestosterone sulphateChEBI
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfateGenerator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfuric acidGenerator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphateGenerator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphuric acidGenerator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfuric acidGenerator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphateGenerator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphuric acidGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfateGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfuric acidGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphateGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphuric acidGenerator
5a-Dihydrotestosterone 17-sulfateGenerator
5a-Dihydrotestosterone 17-sulfuric acidGenerator
5a-Dihydrotestosterone 17-sulphateGenerator
5a-Dihydrotestosterone 17-sulphuric acidGenerator
5alpha-Dihydrotestosterone 17-sulfuric acidGenerator
5alpha-Dihydrotestosterone 17-sulphateGenerator
5alpha-Dihydrotestosterone 17-sulphuric acidGenerator
5Α-dihydrotestosterone 17-sulfateGenerator
5Α-dihydrotestosterone 17-sulfuric acidGenerator
5Α-dihydrotestosterone 17-sulphateGenerator
5Α-dihydrotestosterone 17-sulphuric acidGenerator
DHT-Sulfuric acidGenerator
DHT-Sulphuric acidGenerator
Dihydrotestosterone sulfuric acidGenerator
Dihydrotestosterone sulphuric acidGenerator
5a-Dihydrotestosterone sulfuric acidGenerator
5a-Dihydrotestosterone sulphateGenerator
5a-Dihydrotestosterone sulphuric acidGenerator
5alpha-Dihydrotestosterone sulfateHMDB
5alpha-Dihydrotestosterone sulphateHMDB
Chemical FormulaC19H30O5S
Average Molecular Mass370.504 g/mol
Monoisotopic Mass370.181 g/mol
CAS Registry NumberNot Available
IUPAC Name[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxidanesulfonic acid
Traditional Name5α-dihydrotestosterone sulfate
SMILES[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C19H30O5S/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(24-25(21,22)23)19(15,2)10-8-16(14)18/h12,14-17H,3-11H2,1-2H3,(H,21,22,23)/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyKYVPWJSGFKNNLD-ABEVXSGRSA-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
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxosteroid
  • Oxosteroid
  • 3-oxo-5-alpha-steroid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Cyclic ketone
  • Ketone
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0053 g/LALOGPS
logP0.27ALOGPS
logP3.47ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.59 m³·mol⁻¹ChemAxon
Polarizability40.41 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, Positivesplash10-054o-0359000000-149485897a60b61396e3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0039000000-dbc19fa747f37f721203Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0191000000-bb7a78b507be8c3547bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-3595000000-0842465a9970bd04f71bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-b2c6c394ba2ce2ee8c15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1092000000-887ce248e8af99737137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ei-6090000000-c03f985254acf33f9b4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-0295bc1386cdfbdd92bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-0295bc1386cdfbdd92bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-9011000000-eaffe80174b9298493e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-f30493f615f831a2b06fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0mb9-0982000000-fbfefafbafb34eb8849dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1910000000-7cd7f432c40e91f1db59Spectrum
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 IDHMDB0006278
FooDB IDFDB023873
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2794980
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID18915389
ChEBI ID138026
PubChem Compound ID18665256
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Purvis K, Saksena SK, Landgren BM, Cekan Z, Diczfalusy E: Steroid conjugates in human seminal plasma. Clin Endocrinol (Oxf). 1976 May;5(3):253-61.
2. Purvis K, Saksena SK, Cekan Z, Diczfalusy E, Giner J: Endocrine effects of vasectomy. Clin Endocrinol (Oxf). 1976 May;5(3):263-72.
3. Zhao X, Xu F, Qi B, Hao S, Li Y, Li Y, Zou L, Lu C, Xu G, Hou L: Serum metabolomics study of polycystic ovary syndrome based on liquid chromatography-mass spectrometry. J Proteome Res. 2014 Feb 7;13(2):1101-11. doi: 10.1021/pr401130w. Epub 2014 Jan 24.
4. Sanchez-Guijo A, Oji V, Hartmann MF, Traupe H, Wudy SA: Simultaneous quantification of cholesterol sulfate, androgen sulfates, and progestagen sulfates in human serum by LC-MS/MS. J Lipid Res. 2015 Sep;56(9):1843-51. doi: 10.1194/jlr.D061499. Epub 2015 Aug 2.
5. Xu H, Zheng X, Qian Y, Guan J, Yi H, Zou J, Wang Y, Meng L, Zhao A, Yin S, Jia W: Metabolomics Profiling for Obstructive Sleep Apnea and Simple Snorers. Sci Rep. 2016 Aug 2;6:30958. doi: 10.1038/srep30958.
6. Dehennin L, Jondet M, Scholler R: Androgen and 19-norsteroid profiles in human preovulatory follicles from stimulated cycles: an isotope dilution-mass spectrometric study. J Steroid Biochem. 1987 Mar;26(3):399-405.
7. Gibb W, Jeffery J: 5 -dihydrotestosterone sulphate and cortisone reductase. Biochim Biophys Acta. 1972 Dec 8;280(4):646-51.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=133773
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=133774
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21890434
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24428203
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26239050
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=27480913
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=3586654
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=4648789
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=6408012
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7141722