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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:13 UTC
Update Date2017-12-07 01:49:35 UTC
HMDB IDHMDB0002833
Secondary Accession Numbers
  • HMDB02833
Metabolite Identification
Common NameTestosterone sulfate
DescriptionTestosterone is a predominantly male hormone, though females do produce certain amounts of it. The primary female hormone is estrogen and males also produce certain amounts of this hormone. testosterone causes the appearance of male traits (i.e deepening voice, pubic and facial hairs, muscular build, etc.). The keto group on C-17 is reduced to an alcohol to yield testosterone. Testosterone is a steroid hormone from the androgen group. testosterone is primarily secreted in the testes of males and the ovaries of females although small amounts are secreted by the adrenal glands. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. On average, the adult male body produces about twenty times the amount of testosterone that an adult female's body does. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5-alpha -dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha-reductase(5-alpha-reduktas). DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects. It is important to note that if there is a too low amount of 5-alpha-reductase(5-alfa-reduktas), the body (of a human) will continue growing into a female with testicles.
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
AndroGelMeSH
AstraZeneca brand OF testosteroneMeSH
GlaxoSmithKline brand OF testosteroneMeSH
Hauck brand OF testosteroneMeSH
Schering brand OF testosteroneMeSH
TestolinMeSH
Testosterone-17-sulfate, (17alpha)-isomerMeSH
Testosterone-17-sulfate, ammonium saltMeSH
Testosterone-17-sulfate, sodium saltMeSH
17 beta Hydroxy 4 androsten 3 oneMeSH
17 beta Hydroxy 8 alpha 4 androsten 3 oneMeSH
HisteroneMeSH
SustanonMeSH
17-beta-Hydroxy-4-androsten-3-oneMeSH
Faulding brand OF testosteroneMeSH
Ferring brand OF testosteroneMeSH
8 IsotestosteroneMeSH
8-IsotestosteroneMeSH
Paladin brand OF testosteroneMeSH
Pasadena brand OF testosteroneMeSH
Solvay brand OF testosteroneMeSH
SterotateMeSH
TestosteroneMeSH
Unimed brand OF testosteroneMeSH
Dr. kade brand OF testosteroneMeSH
TestimMeSH
TestopelMeSH
AndropatchMeSH
CEPA brand OF testosteroneMeSH
ortho Brand OF testosteroneMeSH
17-beta-Hydroxy-8 alpha-4-androsten-3-oneMeSH
Auxilium pharmaceuticals inc. brand OF testosteroneMeSH
Bartor brand OF testosteroneMeSH
Ulmer brand OF testosteroneMeSH
Watson brand OF testosteroneMeSH
AndrodermMeSH
AndrotopMeSH
SmithKline beecham brand OF testosteroneMeSH
TestodermMeSH
Chemical FormulaC19H28O5S
Average Molecular Weight368.488
Monoisotopic Molecular Weight368.165744696
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 Number651-45-6
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
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-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
Ontology
Origin
  • Drug or steroid metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 - 156 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.007 g/LALOGPS
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
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, Positivesplash10-0f76-0479000000-bdb3d4908eb17de0bf8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0039000000-3c70201ac318944d2318View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0291000000-40eaf6c5a80279466483View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-4973000000-432f25c70a6a5a3f7b22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-c0079f3c134f1d99c4edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1092000000-705a336c46754ed24422View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008i-4090000000-c74eaf7f9b7239e6720bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Brain
  • Hypothalamus
  • Kidney
  • Liver
  • Muscle
  • Placenta
  • Sperm
  • Testes
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected and Quantified0.0089 (0.0056-0.012) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    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 LinkNot Available
    METLIN ID3558
    PubChem Compound119207
    PDB IDNot Available
    ChEBI ID84094
    References
    Synthesis ReferenceHolden, G. W.; Levi, I.; Bromley, R. Sodium testosterone sulfate. Journal of the American Chemical Society (1949), 71 3844.
    Material Safety Data Sheet (MSDS)Not Available
    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. [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. [PubMed:7439411 ]

    Only showing the first 10 proteins. There are 46 proteins in total.

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
    Gene Name:
    UGT2B28
    Uniprot ID:
    Q9BY64
    Molecular weight:
    38742.9
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
    Gene Name:
    UGT2B4
    Uniprot ID:
    P06133
    Molecular weight:
    60512.035
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
    Gene Name:
    UGT1A4
    Uniprot ID:
    P22310
    Molecular weight:
    60024.535
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
    Gene Name:
    UGT2B15
    Uniprot ID:
    P54855
    Molecular weight:
    61035.815
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
    Gene Name:
    UGT2A1
    Uniprot ID:
    Q9Y4X1
    Molecular weight:
    60771.605
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A9
    Uniprot ID:
    O60656
    Molecular weight:
    59940.495
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
    Gene Name:
    UGT1A3
    Uniprot ID:
    P35503
    Molecular weight:
    60337.835
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
    Gene Name:
    UGT2B17
    Uniprot ID:
    O75795
    Molecular weight:
    61094.915

    Only showing the first 10 proteins. There are 46 proteins in total.