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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:03:43 UTC
Update Date2018-05-20 20:25:01 UTC
HMDB IDHMDB0006278
Secondary Accession Numbers
  • HMDB06278
Metabolite Identification
Common Name5a-Dihydrotestosterone sulfate
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.
Structure
Thumb
Synonyms
ValueSource
5alpha-Dihydrotestosterone sulfateHMDB
5alpha-Dihydrotestosterone sulphateHMDB
DHT-SulfateHMDB
DHT-SulphateHMDB
Dihydrotestosterone sulfateHMDB
Dihydrotestosterone sulphateHMDB
Chemical FormulaC19H30O5S
Average Molecular Weight370.504
Monoisotopic Molecular Weight370.18139476
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
CAS Registry NumberNot Available
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 Identifier
InChI=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
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
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.0053 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-0359000000-149485897a60b61396e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0039000000-dbc19fa747f37f721203View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0191000000-bb7a78b507be8c3547bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-3595000000-0842465a9970bd04f71bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-b2c6c394ba2ce2ee8c15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1092000000-887ce248e8af99737137View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ei-6090000000-c03f985254acf33f9b4fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    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
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB023873
      KNApSAcK IDNot Available
      Chemspider ID18915389
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG ID2794980
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound18665256
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not 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. [PubMed:133773 ]
      2. Purvis K, Saksena SK, Cekan Z, Diczfalusy E, Giner J: Endocrine effects of vasectomy. Clin Endocrinol (Oxf). 1976 May;5(3):263-72. [PubMed:133774 ]
      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. [PubMed:24428203 ]
      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. [PubMed:26239050 ]
      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. [PubMed:27480913 ]
      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. [PubMed:3586654 ]
      7. Gibb W, Jeffery J: 5 -dihydrotestosterone sulphate and cortisone reductase. Biochim Biophys Acta. 1972 Dec 8;280(4):646-51. [PubMed:4648789 ]