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Record Information
Version1.0
Created at2022-05-12 17:05:55 UTC
Updated at2022-05-12 17:17:56 UTC
NP-MRD IDNP0136919
Secondary Accession NumbersNone
Natural Product Identification
Common NameTestosterone sulfate
DescriptionTestosterone sulfate, also known as 17-O-sulfotestosterone or androgel, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. It was first documented in 1980 (PMID: 7439411). Testosterone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 12822484) (PMID: 21849521) (PMID: 3609707).
Structure
Thumb
Synonyms
ValueSource
Testosterone-17beta-sulfateChEBI
Testosterone-17b-sulfateGenerator
Testosterone-17b-sulfuric acidGenerator
Testosterone-17b-sulphateGenerator
Testosterone-17b-sulphuric acidGenerator
Testosterone-17beta-sulfuric acidGenerator
Testosterone-17beta-sulphateGenerator
Testosterone-17beta-sulphuric acidGenerator
Testosterone-17β-sulfateGenerator
Testosterone-17β-sulfuric acidGenerator
Testosterone-17β-sulphateGenerator
Testosterone-17β-sulphuric acidGenerator
Testosterone sulfuric acidGenerator
Testosterone sulphateGenerator
Testosterone sulphuric acidGenerator
17-O-SulfotestosteroneHMDB
17beta-(Sulfooxy)androst-4-en-3-oneHMDB
Testosterone 17-sulfateHMDB
Testosterone 17-sulphateHMDB
Testosterone 17b-sulfateHMDB
Testosterone 17b-sulphateHMDB
Testosterone hydrogen sulfateHMDB
Testosterone hydrogen sulphateHMDB
Testosterone monosulfateHMDB
Testosterone monosulphateHMDB
Testosterone-17-sulfateHMDB
Testosterone-17-sulphateHMDB
AndroGelHMDB
AstraZeneca brand OF testosteroneHMDB
GlaxoSmithKline brand OF testosteroneHMDB
Hauck brand OF testosteroneHMDB
Schering brand OF testosteroneHMDB
TestolinHMDB
Testosterone-17-sulfate, (17alpha)-isomerHMDB
Testosterone-17-sulfate, ammonium saltHMDB
Testosterone-17-sulfate, sodium saltHMDB
17 beta Hydroxy 4 androsten 3 oneHMDB
17 beta Hydroxy 8 alpha 4 androsten 3 oneHMDB
HisteroneHMDB
SustanonHMDB
17-beta-Hydroxy-4-androsten-3-oneHMDB
Faulding brand OF testosteroneHMDB
Ferring brand OF testosteroneHMDB
8 IsotestosteroneHMDB
8-IsotestosteroneHMDB
Paladin brand OF testosteroneHMDB
Pasadena brand OF testosteroneHMDB
Solvay brand OF testosteroneHMDB
SterotateHMDB
TestosteroneHMDB
Unimed brand OF testosteroneHMDB
Dr. kade brand OF testosteroneHMDB
TestimHMDB
TestopelHMDB
AndropatchHMDB
CEPA brand OF testosteroneHMDB
Ortho brand OF testosteroneHMDB
17-beta-Hydroxy-8 alpha-4-androsten-3-oneHMDB
Auxilium pharmaceuticals inc. brand OF testosteroneHMDB
Bartor brand OF testosteroneHMDB
Ulmer brand OF testosteroneHMDB
Watson brand OF testosteroneHMDB
AndrodermHMDB
AndrotopHMDB
SmithKline beecham brand OF testosteroneHMDB
TestodermHMDB
Chemical FormulaC19H28O5S
Average Mass368.4880 Da
Monoisotopic Mass368.16574 Da
IUPAC Name[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]oxidanesulfonic acid
Traditional Nametestosterone 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])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O5S/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/h11,14-17H,3-10H2,1-2H3,(H,21,22,23)/t14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyWAQBISPOEAOCOG-DYKIIFRCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Ketone
  • Cyclic ketone
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.13ALOGPS
logP3.42ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.42 m³·mol⁻¹ChemAxon
Polarizability39.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002833
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023072
KNApSAcK IDNot Available
Chemspider ID106493
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2794968
Wikipedia LinkTestosterone sulfate
METLIN ID3558
PubChem Compound119207
PDB IDNot Available
ChEBI ID84094
Good Scents IDNot Available
References
General References
  1. Takanashi K: [Studies on 2-hydroxyestradiol 17-sulfate derived from fetoplacental unit: the antioxidant as a potential defense substance against preeclampsia]. Yakugaku Zasshi. 2003 Jun;123(6):399-411. doi: 10.1248/yakushi.123.399. [PubMed:12822484 ]
  2. Laatikainen T, Apter D, Wahlstrom T: Steroids in spermatic and peripheral vein blood in testicular feminization. Fertil Steril. 1980 Nov;34(5):461-4. doi: 10.1016/s0015-0282(16)45138-1. [PubMed:7439411 ]
  3. Schulze JJ, Thorngren JO, Garle M, Ekstrom L, Rane A: Androgen sulfation in healthy UDP-glucuronosyl transferase 2B17 enzyme-deficient men. J Clin Endocrinol Metab. 2011 Nov;96(11):3440-7. doi: 10.1210/jc.2011-0521. Epub 2011 Aug 17. [PubMed:21849521 ]
  4. Huf PA, Bourne AR, Watson TG: Identification of testosterone sulfate in the plasma of the male lizard Tiliqua rugosa. Gen Comp Endocrinol. 1987 Jun;66(3):364-8. doi: 10.1016/0016-6480(87)90245-0. [PubMed:3609707 ]