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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:03:43 UTC
Update Date2021-09-14 15:40:13 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
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
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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 ID138026
Food Biomarker OntologyNot Available
VMH ID5ADTSTSTERONES
MarkerDB IDNot Available
Good Scents 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 ]