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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (66)transporters (8) Show 74 proteins XML

enzymes (66)transporters (8) Show 74 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000234

Secondary Accession Numbers

HMDB00234

Metabolite Identification

Common Name

Testosterone

Description

Testosterone is the primary male sex hormone and anabolic steroid from the androstane class of steroids. It is the most important androgen in potency and quantity for vertebrates. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. In addition, testosterone is involved in health and well-being, and the prevention of osteoporosis. Testosterone exerts its action through binding to and activation of the androgen receptor. In mammals, testosterone is metabolized mainly in the liver. Approximately 50% of testosterone is metabolized via conjugation into testosterone glucuronide and to a lesser extent testosterone sulfate by glucuronosyltransferases and sulfotransferases. An additional 40% of testosterone is metabolized in equal proportions into the 17-ketosteroids androsterone and etiocholanolone via the combined actions of 5alpha- and 5beta-reductases, 3alpha-hydroxysteroid dehydrogenase, and 17beta-HSD. Like other steroid hormones, testosterone is derived from cholesterol. The first step in the biosynthesis of testosterone involves the oxidative cleavage of the side-chain of cholesterol by the cholesterol side-chain cleavage enzyme (P450scc, CYP11A1) to give pregnenolone. In the next step, two additional carbon atoms are removed by the CYP17A1 (17alpha-hydroxylase/17,20-lyase) enzyme to yield a variety of C19 steroids. In addition, the 3beta-hydroxyl group is oxidized by 3beta-hydroxysteroid dehydrogenase to produce androstenedione. In the final and rate limiting step, the C17 keto group androstenedione is reduced by 17beta-hydroxysteroid hydrogenase to yield testosterone. Testosterone is synthesized and released by the Leydig cells in the testes that lie between the tubules and comprise less than 5% of the total testicular volume. Testosterone diffuses into the seminiferous tubules where it is essential for maintaining spermatogenesis. Some testosterone binds to an androgen-binding protein (ABP) that is produced by the Sertoli cells and is homologous to the sex-hormone binding globulin that transports testosterone in the general circulation. The ABP carries testosterone in the testicular fluid where it maintains the activity of the accessory sex glands and may also help to retain testosterone within the tubule and bind excess free hormone. Some testosterone is converted to estradiol by Sertoli cell-derived aromatase enzyme. Leydig cell steroidogenesis is controlled primarily by luteinizing hormone with negative feedback of testosterone on the hypothalamic-pituitary axis. The requirement of spermatogenesis for high local concentrations of testosterone means that loss of androgen production is likely to be accompanied by loss of spermatogenesis. Indeed, if testicular androgen production is inhibited by the administration of exogenous androgens then spermatogenesis ceases. This is the basis of using exogenous testosterone as a male contraceptive. The largest amounts of testosterone (>95%) are produced by the testes in men, while the adrenal glands account for most of the remainder. Testosterone is also synthesized in far smaller total quantities in women by the adrenal glands, thecal cells of the ovaries, and, during pregnancy, by the placenta. Testosterone levels fall by about 1% each year in men. Therefore, with increasing longevity and the aging of the population, the number of older men with testosterone deficiency will increase substantially over the next several decades. Serum testosterone levels decrease progressively in aging men, but the rate and magnitude of decrease vary considerably. Approximately 1% of healthy young men have total serum testosterone levels below normal; in contrast, approximately 20% of healthy men over age 60 years have serum testosterone levels below normal. (PMID: 17904450 , 17875487 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000234
     RDKit          3D
Testosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.6249    0.5958   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804    0.5203    0.3746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5243    1.6623    0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1506    1.6668    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.3181    0.4329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3686   -0.7354   -0.1569 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2860   -2.0741   -0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3418   -1.8904   -1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -0.8849   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5804   -1.1115   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310   -0.2062   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7656   -0.1220   -1.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    0.6692    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8957    0.4696    1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.3272   -0.1465 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1005    1.4935   -1.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904   -0.7583    0.7054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5806   -1.8088    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -1.1847    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835    0.2618    1.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6207    1.1145    1.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762    1.0669   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8201    1.2155   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -0.3938   -1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981    1.6836    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301    2.5991    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0961    1.9649   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    2.3851    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520    0.1176    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -0.3785   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -2.4162    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -2.8056   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -1.5185   -2.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916   -2.8598   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153   -2.0072   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826    0.3612    1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577    1.7371    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    1.2492    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793   -0.5226    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    1.3463   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    2.4641   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    1.5352   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -0.7599    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6162   -2.1776   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -2.7023    1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2620   -1.6981    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6585   -1.2404    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650    0.2588    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8354    1.4375    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 21 49  1  0
M  END


  Mrv1652311131908212D          

 24 27  0  0  1  0            999 V2000
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4290    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134    0.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.2374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134    1.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4685    2.6894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  9  2  0  0  0  0
  1  3  1  0  0  0  0
  4  2  1  0  0  0  0
  4  7  1  0  0  0  0
  5  4  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  6  0  0  0
  6  5  1  0  0  0  0
  6  3  1  0  0  0  0
 16  6  1  0  0  0  0
  6 15  1  1  0  0  0
  8  7  1  0  0  0  0
 23  8  1  0  0  0  0
 23  9  1  0  0  0  0
 10 11  1  0  0  0  0
 17 11  1  0  0  0  0
 16 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 21  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  6  0  0  0
 17 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 24  2  0  0  0  0
  4 19  1  1  0  0  0
 17 20  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000234

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
MUMGGOZAMZWBJJ-DYKIIFRCSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.4244

> <EXACT_MASS>
288.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.875628274645216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.365423297666668

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377705208106928

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.08686012168563

> <JCHEM_PKA_STRONGEST_BASIC>
-0.883941123357545

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.42979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000234
     RDKit          3D
Testosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.6249    0.5958   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804    0.5203    0.3746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5243    1.6623    0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1506    1.6668    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.3181    0.4329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3686   -0.7354   -0.1569 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2860   -2.0741   -0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3418   -1.8904   -1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -0.8849   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5804   -1.1115   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310   -0.2062   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7656   -0.1220   -1.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    0.6692    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8957    0.4696    1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.3272   -0.1465 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1005    1.4935   -1.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904   -0.7583    0.7054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5806   -1.8088    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -1.1847    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835    0.2618    1.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6207    1.1145    1.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762    1.0669   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8201    1.2155   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -0.3938   -1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981    1.6836    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301    2.5991    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0961    1.9649   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    2.3851    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520    0.1176    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -0.3785   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -2.4162    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -2.8056   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -1.5185   -2.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916   -2.8598   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153   -2.0072   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826    0.3612    1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577    1.7371    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    1.2492    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793   -0.5226    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    1.3463   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    2.4641   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    1.5352   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -0.7599    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6162   -2.1776   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -2.7023    1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2620   -1.6981    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6585   -1.2404    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650    0.2588    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8354    1.4375    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 21 49  1  0
M  END

HEADER    PROTEIN                                 13-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-19         0                                  
HETATM    1  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.132   1.064   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.037   2.310   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.334   2.310   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       2.667   0.000   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.132   3.556   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.608   5.020   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    9    4                                                  
CONECT    3    1    6                                                       
CONECT    4    2    7    5   19                                             
CONECT    5    4   10   14    6                                             
CONECT    6    5    3   16   15                                             
CONECT    7    4    8                                                       
CONECT    8    7   23                                                       
CONECT    9    2   23                                                       
CONECT   10    5   11                                                       
CONECT   11   10   17                                                       
CONECT   12   16   13                                                       
CONECT   13   12   21                                                       
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16    6   12   17   18                                             
CONECT   17   11   16   21   20                                             
CONECT   18   16                                                            
CONECT   19    4                                                            
CONECT   20   17                                                            
CONECT   21   13   17   22                                                  
CONECT   22   21                                                            
CONECT   23    8    9   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000234
HETATM    1  C1  UNL     1      -2.625   0.596  -1.088  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.380   0.520   0.375  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.524   1.662   0.854  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.151   1.667   0.294  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.547   0.318   0.433  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.369  -0.735  -0.157  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.286  -2.074  -0.301  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.342  -1.890  -1.400  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.294  -0.885  -0.874  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.580  -1.112  -1.086  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.631  -0.206  -0.625  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.766  -0.122  -1.132  1.00  0.00           O  
HETATM   13  C12 UNL     1       4.309   0.669   0.531  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.896   0.470   1.009  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.915   0.327  -0.146  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.100   1.494  -1.127  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.590  -0.758   0.705  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.581  -1.809   0.406  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.912  -1.185   0.850  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.583   0.262   1.205  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.621   1.115   1.063  1.00  0.00           O  
HETATM   22  H1  UNL     1      -3.576   1.067  -1.383  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.820   1.215  -1.565  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.599  -0.394  -1.609  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.498   1.684   1.954  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.030   2.599   0.533  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.096   1.965  -0.771  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.453   2.385   0.901  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.552   0.118   1.546  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.600  -0.379  -1.201  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.793  -2.416   0.632  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.469  -2.806  -0.584  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.799  -1.519  -2.290  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.792  -2.860  -1.590  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.915  -2.007  -1.628  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.983   0.361   1.362  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.458   1.737   0.317  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.616   1.249   1.715  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.879  -0.523   1.537  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.428   1.346  -1.976  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.877   2.464  -0.648  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.122   1.535  -1.497  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.307  -0.760   1.758  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.616  -2.178  -0.617  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.364  -2.702   1.058  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.262  -1.698   1.767  1.00  0.00           H  
HETATM   47  H26 UNL     1      -4.659  -1.240   0.037  1.00  0.00           H  
HETATM   48  H27 UNL     1      -3.265   0.259   2.276  1.00  0.00           H  
HETATM   49  H28 UNL     1      -4.835   1.437   0.178  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7   17   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   10   15
CONECT   10   11   35
CONECT   11   12   12   13
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16
CONECT   16   40   41   42
CONECT   17   18   43
CONECT   18   19   44   45
CONECT   19   20   46   47
CONECT   20   21   48
CONECT   21   49
END

HMDB0000234
     RDKit          3D
Testosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.6249    0.5958   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804    0.5203    0.3746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5243    1.6623    0.8541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1506    1.6668    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.3181    0.4329 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3686   -0.7354   -0.1569 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2860   -2.0741   -0.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3418   -1.8904   -1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2935   -0.8849   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5804   -1.1115   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6310   -0.2062   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7656   -0.1220   -1.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3091    0.6692    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8957    0.4696    1.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149    0.3272   -0.1465 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1005    1.4935   -1.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904   -0.7583    0.7054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5806   -1.8088    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -1.1847    0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835    0.2618    1.2053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6207    1.1145    1.0630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762    1.0669   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8201    1.2155   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -0.3938   -1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4981    1.6836    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0301    2.5991    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0961    1.9649   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531    2.3851    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5520    0.1176    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -0.3785   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7931   -2.4162    0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4688   -2.8056   -0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7987   -1.5185   -2.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916   -2.8598   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153   -2.0072   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9826    0.3612    1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577    1.7371    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    1.2492    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793   -0.5226    1.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4283    1.3463   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    2.4641   -0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1225    1.5352   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -0.7599    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6162   -2.1776   -0.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3641   -2.7023    1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2620   -1.6981    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6585   -1.2404    0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650    0.2588    2.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8354    1.4375    0.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  1
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 21 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17beta-Hydroxy-4-androsten-3-one	ChEBI
4-Androsten-17beta-ol-3-one	ChEBI
Androderm	ChEBI
Testosteron	ChEBI
Testosterona	ChEBI
Testosteronum	ChEBI
Androgel	Kegg
Axiron	Kegg
Striant	Kegg
Testim	Kegg
17b-Hydroxy-4-androsten-3-one	Generator
17Β-hydroxy-4-androsten-3-one	Generator
4-Androsten-17b-ol-3-one	Generator
4-Androsten-17β-ol-3-one	Generator
(+)-Testosterone	HMDB
(+-)-8-Iso-testosterone	HMDB
(+-)-Retrotestosterone	HMDB
(+-)-Testosterone	HMDB
(17b)-17-Hydroxy-androst-4-en-3-one	HMDB
13-Iso-testosterone	HMDB
17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one	HMDB
17-Hydroxy-androst-4-en-3-one	HMDB
17-Hydroxy-D4-androsten-3-one	HMDB
17a-Hydroxy-(13a)-androst-4-en-3-one	HMDB
17a-Hydroxy-13a-androst-4-en-3-one	HMDB
17a-Hydroxy-14b-androst-4-en-3-one	HMDB
17a-Hydroxy-androst-4-en-3-one	HMDB
17b-Hydroxy-(10a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(13a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(8a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(8a,10a)-androst-4-en-3-one	HMDB
17b-Hydroxy-(9b)-androst-4-en-3-one	HMDB
17b-Hydroxy-(9b,10a)-androst-4-en-3-one	HMDB
17b-Hydroxy-13a-androst-4-en-3-one	HMDB
17b-Hydroxy-8a-androst-4-en-3-one	HMDB
17b-Hydroxy-androst-4-en-3-ON	HMDB
17b-Hydroxy-androst-4-en-3-one	HMDB
17b-Hydroxy-D4-androsten-3-one	HMDB
17b-Hydroxyandrost-4-en-3-one	HMDB
17b-Hydroxyandrost-4-ene-3-one	HMDB
17b-Testosterone	HMDB
4-Androsten-3-one-17b-ol	HMDB
8-Iso-testosterone	HMDB
9b,10a-Testosterone	HMDB
9b-Testosterone	HMDB
Androlin	HMDB
Andronaq	HMDB
Andropatch	HMDB
Androst-4-en-17b-ol-3-one	HMDB
Androst-4-ene-17b-ol-3-one	HMDB
Andrusol	HMDB
Cristerona T	HMDB
D4-Androsten-17b-ol-3-one	HMDB
Epitestosteron	HMDB
Geno-cristaux gremy	HMDB
Homosteron	HMDB
Homosterone	HMDB
Lumitestosteron	HMDB
Mertestate	HMDB
Neotestis	HMDB
Oreton	HMDB
Orquisteron	HMDB
Perandren	HMDB
Percutacrine androgenique	HMDB
Primotest	HMDB
Primoteston	HMDB
rac-17b-Hydroxy-(13a)androst-4-en-3-one	HMDB
rac-17b-Hydroxy-(8a)-androst-4-en-3-one	HMDB
rac-17b-Hydroxy-(9b,10a)androst-4-en-3-one	HMDB
rac-17b-Hydroxy-androst-4-en-3-one	HMDB
Relibra	HMDB
Retrotestosterone	HMDB
Sustanon	HMDB
Sustanone	HMDB
Sustason 250	HMDB
Synandrol F	HMDB
Teslen	HMDB
Testandrone	HMDB
Testiculosterone	HMDB
Testobase	HMDB
Testoderm	HMDB
Testogel	HMDB
Testolent	HMDB
Testolin	HMDB
Testopropon	HMDB
Testosteroid	HMDB
Testoviron schering	HMDB
Testoviron T	HMDB
Testro aq	HMDB
Testrone	HMDB
Testryl	HMDB
Tostrelle	HMDB
Tostrex	HMDB
Viatrel	HMDB
Virormone	HMDB
Virosterone	HMDB
Androtop	HMDB
CEPA brand OF testosterone	HMDB
Histerone	HMDB
SmithKline beecham brand OF testosterone	HMDB
Solvay brand OF testosterone	HMDB
Sterotate	HMDB
17-beta-Hydroxy-8 alpha-4-androsten-3-one	HMDB
AstraZeneca brand OF testosterone	HMDB
Bartor brand OF testosterone	HMDB
Dr. kade brand OF testosterone	HMDB
Ferring brand OF testosterone	HMDB
Hauck brand OF testosterone	HMDB
Pasadena brand OF testosterone	HMDB
Testosterone sulfate	HMDB
Ulmer brand OF testosterone	HMDB
Unimed brand OF testosterone	HMDB
Watson brand OF testosterone	HMDB
17-beta-Hydroxy-4-androsten-3-one	HMDB
8 Isotestosterone	HMDB
8-Isotestosterone	HMDB
Auxilium pharmaceuticals inc. brand OF testosterone	HMDB
Faulding brand OF testosterone	HMDB
Paladin brand OF testosterone	HMDB
Schering brand OF testosterone	HMDB
17 beta Hydroxy 4 androsten 3 one	HMDB
17 beta Hydroxy 8 alpha 4 androsten 3 one	HMDB
GlaxoSmithKline brand OF testosterone	HMDB
Ortho brand OF testosterone	HMDB
Testopel	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

IUPAC Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

58-22-0

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

MUMGGOZAMZWBJJ-DYKIIFRCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:17347 )
17beta-hydroxy steroid (CHEBI:17347 )
androstanoid (CHEBI:17347 )
androstane (C00535 )
C19 steroids (androgens) and derivatives (C00535 )
Androstane and derivatives (C00535 )
Androgens (C00535 )
C19 steroids (androgens) and derivatives (LMST02020002 )

Ontology

Not Available

Skeletal Muscle (HMDB: HMDB0000234)

Biofluid or Excreta

Non-excretory biofluid

Semen (HMDB: HMDB0000234)
Saliva (PMID: 954994)
Blood (PMID: 11939709)
Cerebrospinal Fluid (CSF) (PMID: 10625505)

Excreta

Urine (PMID: 15716191)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000234)

Tissue substructure

Muscle (HMDB: HMDB0000234)

Cell

Germ cell

Spermatozoon (HMDB: HMDB0000234)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Androgen and Estrogen Metabolism (HMDB: HMDB0000234)
Androstenedione Metabolism (PathBank: SMP0030406)

Disease pathway

Role

Biological role

Industrial application

Pharmaceutical industry

Biomarker

11-beta-hydroxylase deficiency (HMDB: HMDB0000234)
Aromatase Deficiency (HMDB: HMDB0000234)
21-hydroxylase deficiency (HMDB: HMDB0000234)
X-Linked Ichthyosis (HMDB: HMDB0000234)
Cadmium Exposure (HMDB: HMDB0000234)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.023 mg/mL	Not Available
LogP	3.32	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	175.645	30932474
[M+H]+	MetCCS_train_pos	172.682	30932474
[M-H]-	Not Available	175.645	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000186
[M+H]+	Not Available	178.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000186

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.033 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.37	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.43 m³·mol⁻¹	ChemAxon
Polarizability	33.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.257	31661259
DarkChem	[M-H]-	167.313	31661259
AllCCS	[M+H]+	174.167	32859911
AllCCS	[M-H]-	178.51	32859911
DeepCCS	[M-2H]-	205.864	30932474
DeepCCS	[M+Na]+	179.989	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	171.1	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.8	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	178.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Testosterone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3544.2	Standard polar	33892256
Testosterone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2567.6	Standard non polar	33892256
Testosterone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2768.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Testosterone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2764.5	Semi standard non polar	33892256
Testosterone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O	2636.1	Semi standard non polar	33892256
Testosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2694.5	Semi standard non polar	33892256
Testosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2693.2	Standard non polar	33892256
Testosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2974.7	Standard polar	33892256
Testosterone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3021.3	Semi standard non polar	33892256
Testosterone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@H](O)[C@@]3(C)CC[C@@H]12	2917.7	Semi standard non polar	33892256
Testosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3233.8	Semi standard non polar	33892256
Testosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3170.2	Standard non polar	33892256
Testosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3231.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (1 TMS)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (2 TMS)	splash10-053u-1920200000-db3504f562c54e6e1bbb	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-356ddfa8ddf8e551278d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone EI-B (Non-derivatized)	splash10-0597-7920000000-dde7fba02fcbcec2d665	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone EI-B (Non-derivatized)	splash10-05fs-4920000000-ccd839134de79f179f9e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone EI-B (Non-derivatized)	splash10-00ds-0950000000-c65fc8043083ad93d169	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (Non-derivatized)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (Non-derivatized)	splash10-053u-1920200000-db3504f562c54e6e1bbb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (Non-derivatized)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Testosterone GC-MS (Non-derivatized)	splash10-004l-3910000000-356ddfa8ddf8e551278d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testosterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-074i-0390000000-09e2a725ebd92c93dc88	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testosterone GC-MS (1 TMS) - 70eV, Positive	splash10-001j-3349000000-75c3f3e0341bb42eb819	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testosterone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testosterone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Testosterone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dv-5940000000-5e22fba0c369374c75df	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0090000000-914b212f1dbb7fb7b1ac	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-052b-9800000000-d2e38d44d2f16d0a4203	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-052b-9300000000-6830823fa12b40e784a2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone EI-B (JEOL JMS-01-SG-2) , Positive-QTOF	splash10-0597-7920000000-dde7fba02fcbcec2d665	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone EI-B (HITACHI RMU-6E) , Positive-QTOF	splash10-05fs-4920000000-ccd839134de79f179f9e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone EI-B (HITACHI M-80) , Positive-QTOF	splash10-00ds-0950000000-48c1f79091d708072f30	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone LC-ESI-ITFT , positive-QTOF	splash10-0a4j-6900000000-3d818ffe03ecd499e078	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone LC-ESI-ITFT , positive-QTOF	splash10-0a4j-7900000000-6db3d23d98d548cbbfaa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone LC-ESI-ITFT , positive-QTOF	splash10-0ukj-2690000000-14b953cb16c53d1e2744	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone LC-ESI-ITFT , positive-QTOF	splash10-0uka-2790000000-dcd6839af64c3ef6006e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone LC-ESI-ITFT , positive-QTOF	splash10-0006-0090000000-b5f0189f1d6f21b90673	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone LC-ESI-ITFT , positive-QTOF	splash10-0006-0090000000-21e1bde01931b051a4a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone 30V, Positive-QTOF	splash10-0fe1-0940000000-acd7cb439468ece54d34	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone 50V, Positive-QTOF	splash10-00am-0900000000-9f695ef54b7a75aa0ca5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone 55V, Positive-QTOF	splash10-0a4j-6900000000-cc148be066f76bf120a2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone 80V, Positive-QTOF	splash10-0a4j-8900000000-5a1a78a963c17ee2f26b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone 35V, Positive-QTOF	splash10-0ukj-2690000000-075abfa2a19ae84712fb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone 55V, Positive-QTOF	splash10-0uka-2790000000-528f02372cf3ac228b4a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Testosterone 35V, Positive-QTOF	splash10-052k-7950000000-7505adc1ceff21713130	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testosterone 10V, Positive-QTOF	splash10-00dr-0190000000-4b469479ef097f60ed90	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testosterone 20V, Positive-QTOF	splash10-00dr-0390000000-8bebba5f70c72e80b630	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testosterone 40V, Positive-QTOF	splash10-0udi-5890000000-46ba5a59d051001f2a63	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testosterone 10V, Negative-QTOF	splash10-000i-0090000000-3c963477109db1f6b39e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testosterone 20V, Negative-QTOF	splash10-000i-0090000000-87d4a2534cd39e8c54a8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Testosterone 40V, Negative-QTOF	splash10-0abc-1190000000-abbd0808a06f67c1f6fc	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

Brain
Ovary
Semen
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available
Androstenedione Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00260-0.0139 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.000693-0.00277 uM	Not Specified	Not Specified	Normal	11038205	details
Blood	Detected and Quantified	0.0156-0.0347 uM	Adult (>18 years old)	Male	Normal	6876115	details
Blood	Detected and Quantified	0.00139 +/- 0.000763 uM	Adult (>18 years old)	Female	Normal	11826238	details
Blood	Detected and Quantified	0.00004-0.00215 uM	Children (1-13 years old)	Female	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0-0.00098 uM	Children (1-13 years old)	Female	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.00036-0.0017 uM	Adolescent (13-18 years old)	Female	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0-0.000198 uM	Infant (0-1 year old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0-0.00012 uM	Children (1-13 years old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0-0.0154 uM	Children (1-13 years old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.00125-0.0276 uM	Adolescent (13-18 years old)	Male	Normal	CALIPER Paediatri...	details
Blood	Detected and Quantified	0.00125 +/- 0.00042 uM	Adult (>18 years old)	Female	Normal	17186999	details
Blood	Detected and Quantified	0.013 (0.0083-0.0286) uM	Adult (>18 years old)	Male	Normal	18716488	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Blood	Detected and Quantified	<0.000400 uM	Not Specified	Both	Normal	8933406	details
Blood	Detected and Quantified	0.00800 - 0.0400 uM	Adult (>18 years old)	Male	Normal	Molecular You	details
Blood	Detected and Quantified	0.000200 - 0.00300 uM	Adult (>18 years old)	Female	Normal	GID.info	details
Blood	Detected and Quantified	0.00936 uM	Adult (>18 years old)	Male	Normal	16477341	details
Blood	Detected and Quantified	0.0171 +/- 0.00510 uM	Children (1-13 years old)	Both	Normal	26079780	details
Blood	Detected and Quantified	0.0094 +/- 0.0014 uM	Adult (>18 years old)	Male	Normal	10625505	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00101 (0.00002-0.002) uM	Adult (>18 years old)	Not Specified	Normal	1620285	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00065 +/- 0.00012 uM	Adult (>18 years old)	Male	Normal	10625505	details
Saliva	Detected and Quantified	0.00120 (0.00108-0.00133) uM	Adult (>18 years old)	Male	Normal	954994	details
Saliva	Detected and Quantified	0.000677 (0.000590-0.000764) uM	Adult (>18 years old)	Female	Normal	954994	details
Saliva	Detected and Quantified	0.00034 +/- 0.00011 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.00042 +/- 0.00013 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.00033 +/- 0.00014 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.00031 +/- 0.00015 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.00027 +/- 0.00013 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.00028 +/- 0.00013 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000077 +/- 0.000036 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.000069 +/- 0.000036 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.00037 +/- 0.00016 uM	Adult (>18 years old)	Both	Normal	24033227	details
Saliva	Detected and Quantified	0.00035 +/- 0.00015 uM	Adult (>18 years old)	Both	Normal	24033227	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	1.07 +/- 0.19 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9812172 16886650 Mayo Medical Labo... Kushnir MM, Rockw...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.000104 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Blood	Detected and Quantified	0.000624-0.0156 uM	Newborn (0-30 days old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	27476613	details
Blood	Detected and Quantified	9.31 (3.31-19.95) uM	Adult (>18 years old)	Male	Cadmium exposure	11939709	details
Blood	Detected and Quantified	0.00385 uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	11038205	details
Blood	Detected and Quantified	0.00121-0.0118 uM	Adult (>18 years old)	Male	Woodhouse-Sakati syndrome	6876115	details
Blood	Detected and Quantified	0.00198-0.00368 uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	11826238	details
Blood	Detected and Quantified	0.010 +/- 0.013 uM	Adolescent (13-18 years old)	Male	Hypogonadism	http://en.wi...	details
Blood	Detected and Quantified	0.00900-0.0360 uM	Adult (>18 years old)	Male	X-linked ichthyosis	3864567	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Prostate cancer	20975847	details
Blood	Detected and Quantified	<0.000140 uM	Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	9077535	details
Blood	Detected and Quantified	<0.000140 uM	Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	9077535	details
Blood	Detected and Quantified	0.00243 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	7951484	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details
Blood	Detected and Quantified	0.00150-0.00420 uM	Children (1-13 years old)	Both	11-beta-hydroxylase deficiency	8933406	details
Blood	Detected and Quantified	<0.000002 uM	Children (1-13 years old)	Female	Aromatase deficiency	9177373	details
Blood	Detected and Quantified	<0.000693 uM	Adolescent (13-18 years old)	Female	Adrenal hyperplasia, congenital, due to 17-alpha-hydroxylase deficiency	16477341	details
Blood	Detected and Quantified	0.00933 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.00184 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00003400 +/- 0.00001665 uM	Adult (>18 years old)	Not Specified	Leuprolide acetate-induced hypogonadism	16585475	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000497 +/- 0.000222 uM	Adult (>18 years old)	Not Specified	Leuprolide acetate-induced hypogonadism with testosterone replacment	16585475	details

Associated Disorders and Diseases

Disease References

Hypogonadism
http://en.wikipedia.org/wiki/Testosterone [Link]
Cadmium exposure
Zeng X, Lin T, Zhou Y, Kong Q: Alterations of serum hormone levels in male workers occupationally exposed to cadmium. J Toxicol Environ Health A. 2002 Apr 12;65(7):513-21. [PubMed:11939709 ]
Prostate cancer
Madu CO, Lu Y: Novel diagnostic biomarkers for prostate cancer. J Cancer. 2010 Oct 6;1:150-77. [PubMed:20975847 ]
Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ] Benkert AR, Young M, Robinson D, Hendrickson C, Lee PA, Strauss KA: Severe Salt-Losing 3beta-Hydroxysteroid Dehydrogenase Deficiency: Treatment and Outcomes of HSD3B2 c.35G>A Homozygotes. J Clin Endocrinol Metab. 2015 Aug;100(8):E1105-15. doi: 10.1210/jc.2015-2098. Epub 2015 Jun 16. [PubMed:26079780 ] Guven A, Polat S: Testicular Adrenal Rest Tumor in Two Brothers with a Novel Mutation in the 3-Beta-Hydroxysteroid Dehydrogenase-2 Gene. J Clin Res Pediatr Endocrinol. 2017 Mar 1;9(1):85-90. doi: 10.4274/jcrpe.3306. Epub 2016 Jul 29. [PubMed:27476613 ]
11-beta-Hydroxylase deficiency
Burren CP, Montalto J, Yong AB, Batch JA: CYP11 beta 1 (11-beta-hydroxylase) deficiency in congenital adrenal hyperplasia. J Paediatr Child Health. 1996 Oct;32(5):433-8. [PubMed:8933406 ]
Aromatase deficiency
Mullis PE, Yoshimura N, Kuhlmann B, Lippuner K, Jaeger P, Harada H: Aromatase deficiency in a female who is compound heterozygote for two new point mutations in the P450arom gene: impact of estrogens on hypergonadotropic hypogonadism, multicystic ovaries, and bone densitometry in childhood. J Clin Endocrinol Metab. 1997 Jun;82(6):1739-45. doi: 10.1210/jcem.82.6.3994. [PubMed:9177373 ]
21-Hydroxylase deficiency
Warinner SA, Zimmerman D, Thompson GB, Grant CS: Study of three patients with congenital adrenal hyperplasia treated by bilateral adrenalectomy. World J Surg. 2000 Nov;24(11):1347-52. [PubMed:11038205 ] Gmyrek GA, New MI, Sosa RE, Poppas DP: Bilateral laparoscopic adrenalectomy as a treatment for classic congenital adrenal hyperplasia attributable to 21-hydroxylase deficiency. Pediatrics. 2002 Feb;109(2):E28. [PubMed:11826238 ]
Congenital Adrenal Hyperplasia, due to 17-Hydroxylase-Deficiency
Wong SL, Shu SG, Tsai CR: Seventeen alpha-hydroxylase deficiency. J Formos Med Assoc. 2006 Feb;105(2):177-81. doi: 10.1016/S0929-6646(09)60342-9. [PubMed:16477341 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]
Woodhouse-Sakati syndrome
Woodhouse NJ, Sakati NA: A syndrome of hypogonadism, alopecia, diabetes mellitus, mental retardation, deafness, and ECG abnormalities. J Med Genet. 1983 Jun;20(3):216-9. [PubMed:6876115 ]
X-linked ichthyosis
Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
Lipoid Congenital Adrenal Hyperplasia
Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284. [PubMed:9077535 ]

Associated OMIM IDs

146110 (Hypogonadism)
176807 (Prostate cancer)
181500 (Schizophrenia)
201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
202010 (11-beta-Hydroxylase deficiency)
613546 (Aromatase deficiency)
201910 (21-Hydroxylase deficiency)
202110 (Congenital Adrenal Hyperplasia, due to 17-Hydroxylase-Deficiency)
613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)
241080 (Woodhouse-Sakati syndrome)
308100 (X-linked ichthyosis)
201710 (Lipoid Congenital Adrenal Hyperplasia)

External Links

DrugBank ID

DB00624

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00003675

Chemspider ID

5791

KEGG Compound ID

C00535

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Testosterone

METLIN ID

Not Available

PubChem Compound

6013

PDB ID

Not Available

ChEBI ID

17347

Food Biomarker Ontology

Not Available

VMH ID

TSTSTERONE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ercoli, Alberto; De Ruggieri, Pietro. An improved method of preparing testosterone, dihydrotestosterone, and some of their esters. Journal of the American Chemical Society (1953), 75 650-3.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95. [PubMed:10625505 ]
Cutolo M, Sulli A, Capellino S, Villaggio B, Montagna P, Pizzorni C, Paolino S, Seriolo B, Felli L, Straub RH: Anti-TNF and sex hormones. Ann N Y Acad Sci. 2006 Jun;1069:391-400. [PubMed:16855166 ]
Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. [PubMed:1620285 ]
Schaap LA, Pluijm SM, Smit JH, van Schoor NM, Visser M, Gooren LJ, Lips P: The association of sex hormone levels with poor mobility, low muscle strength and incidence of falls among older men and women. Clin Endocrinol (Oxf). 2005 Aug;63(2):152-60. [PubMed:16060908 ]
Archer JS, Love-Geffen TE, Herbst-Damm KL, Swinney DA, Chang JR: Effect of estradiol versus estradiol and testosterone on brain-activation patterns in postmenopausal women. Menopause. 2006 May-Jun;13(3):528-37. [PubMed:16735951 ]
Handelsman DJ: Clinical review: The rationale for banning human chorionic gonadotropin and estrogen blockers in sport. J Clin Endocrinol Metab. 2006 May;91(5):1646-53. Epub 2006 Feb 14. [PubMed:16478815 ]
Duschek EJ, Gooren LJ, Netelenbos C: Comparison of effects of the rise in serum testosterone by raloxifene and oral testosterone on serum insulin-like growth factor-1 and insulin-like growth factor binding protein-3. Maturitas. 2005 Jul 16;51(3):286-93. [PubMed:15978972 ]
Huang I, Jones J, Khorram O: Human seminal plasma nitric oxide: correlation with sperm morphology and testosterone. Med Sci Monit. 2006 Mar;12(3):CR103-6. Epub 2006 Feb 23. [PubMed:16501419 ]
Hussein A, Ozgok Y, Ross L, Niederberger C: Clomiphene administration for cases of nonobstructive azoospermia: a multicenter study. J Androl. 2005 Nov-Dec;26(6):787-91; discussion 792-3. [PubMed:16291975 ]
Ahtiainen JP, Pakarinen A, Alen M, Kraemer WJ, Hakkinen K: Short vs. long rest period between the sets in hypertrophic resistance training: influence on muscle strength, size, and hormonal adaptations in trained men. J Strength Cond Res. 2005 Aug;19(3):572-82. [PubMed:16095405 ]
Landman AD, Sanford LM, Howland BE, Dawes C, Pritchard ET: Testosterone in human saliva. Experientia. 1976;32(7):940-1. [PubMed:954994 ]
Knickmeyer RC, Wheelwright S, Taylor K, Raggatt P, Hackett G, Baron-Cohen S: Gender-typed play and amniotic testosterone. Dev Psychol. 2005 May;41(3):517-28. [PubMed:15910159 ]
Fejes I, Koloszar S, Szollosi J, Zavaczki Z, Pal A: Is semen quality affected by male body fat distribution? Andrologia. 2005 Oct;37(5):155-9. [PubMed:16266392 ]
Jarow JP, Zirkin BR: The androgen microenvironment of the human testis and hormonal control of spermatogenesis. Ann N Y Acad Sci. 2005 Dec;1061:208-20. [PubMed:16467270 ]
Rovensky J, Radikova Z, Imrich R, Greguska O, Vigas M, Macho L: Gonadal and adrenal steroid hormones in plasma and synovial fluid of patients with rheumatoid arthritis. Endocr Regul. 2004 Dec;38(4):143-9. [PubMed:15841793 ]
Klimek M, Pabian W, Tomaszewska B, Kolodziejczyk J: Levels of plasma ACTH in men from infertile couples. Neuro Endocrinol Lett. 2005 Aug;26(4):347-50. [PubMed:16136011 ]
Shores MM, Matsumoto AM, Sloan KL, Kivlahan DR: Low serum testosterone and mortality in male veterans. Arch Intern Med. 2006 Aug 14-28;166(15):1660-5. [PubMed:16908801 ]
Bhasin S, Cunningham GR, Hayes FJ, Matsumoto AM, Snyder PJ, Swerdloff RS, Montori VM: Testosterone therapy in adult men with androgen deficiency syndromes: an endocrine society clinical practice guideline. J Clin Endocrinol Metab. 2006 Jun;91(6):1995-2010. Epub 2006 May 23. [PubMed:16720669 ]
Jarow JP, Wright WW, Brown TR, Yan X, Zirkin BR: Bioactivity of androgens within the testes and serum of normal men. J Androl. 2005 May-Jun;26(3):343-8. [PubMed:15867001 ]
Bridger T, MacDonald S, Baltzer F, Rodd C: Randomized placebo-controlled trial of metformin for adolescents with polycystic ovary syndrome. Arch Pediatr Adolesc Med. 2006 Mar;160(3):241-6. [PubMed:16520442 ]
Kazi M, Geraci SA, Koch CA: Considerations for the diagnosis and treatment of testosterone deficiency in elderly men. Am J Med. 2007 Oct;120(10):835-40. [PubMed:17904450 ]
Krone N, Hanley NA, Arlt W: Age-specific changes in sex steroid biosynthesis and sex development. Best Pract Res Clin Endocrinol Metab. 2007 Sep;21(3):393-401. [PubMed:17875487 ]
Authors unspecified: Contraceptive efficacy of testosterone-induced azoospermia in normal men. World Health Organization Task Force on methods for the regulation of male fertility. Lancet. 1990 Oct 20;336(8721):955-9. [PubMed:1977002 ]
Hoberman JM, Yesalis CE: The history of synthetic testosterone. Sci Am. 1995 Feb;272(2):76-81. [PubMed:7817189 ]
Freeman ER, Bloom DA, McGuire EJ: A brief history of testosterone. J Urol. 2001 Feb;165(2):371-3. [PubMed:11176375 ]

Only showing the first 10 proteins. There are 74 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

References

Sjoberg RL, Ducci F, Barr CS, Newman TK, Dell'osso L, Virkkunen M, Goldman D: A non-additive interaction of a functional MAO-A VNTR and testosterone predicts antisocial behavior. Neuropsychopharmacology. 2008 Jan;33(2):425-30. Epub 2007 Apr 11. [PubMed:17429405 ]
Hoff KM: Interaction of testosterone with monoamineoxidase in mouse brain maturation. Gen Pharmacol. 1977;8(1):55-7. [PubMed:590724 ]

Enzyme Details

2. Estrogen sulfotransferase

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
Gene Name:: SULT1E1
Uniprot ID:: P49888
Molecular weight:: 35126.185

Enzyme Details

3. Aldo-keto reductase family 1 member C3

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:: AKR1C3
Uniprot ID:: P42330
Molecular weight:: 36866.91

Reactions

Testosterone + NAD → Androstenedione + NADH	details
Testosterone + NADP → Androstenedione + NADPH	details

Enzyme Details

4. Estradiol 17-beta-dehydrogenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:: HSD17B2
Uniprot ID:: P37059
Molecular weight:: 42784.75

Reactions

Testosterone + NAD → Androstenedione + NADH	details
Testosterone + NAD → Androstenedione + NADH + Hydrogen Ion	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B28

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

Reactions

Testosterone + Uridine diphosphate glucuronic acid → Testosterone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. Estradiol 17-beta-dehydrogenase 8

General function:: Involved in oxidoreductase activity
Specific function:: NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:: HSD17B8
Uniprot ID:: Q92506
Molecular weight:: 26973.56

Reactions

Testosterone + NAD → Androstenedione + NADH	details
Testosterone + NAD → Androstenedione + NADH + Hydrogen Ion	details

Enzyme Details

7. UDP-glucuronosyltransferase 2B4

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

Reactions

Testosterone + Uridine diphosphate glucuronic acid → Testosterone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 1-4

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

Reactions

Testosterone + Uridine diphosphate glucuronic acid → Testosterone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 2B10

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:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Testosterone + Uridine diphosphate glucuronic acid → Testosterone glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 2B7

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

Reactions

Testosterone + Uridine diphosphate glucuronic acid → Testosterone glucuronide + Uridine 5'-diphosphate	details

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. Eur J Pharm Sci. 2001 Feb;12(4):505-13. [PubMed:11231118 ]
Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. [PubMed:12668685 ]

Enzyme Details

3. Solute carrier family 22 member 4

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:: SLC22A4
Uniprot ID:: Q9H015
Molecular weight:: 62154.5

References

Tzvetkov MV, Vormfelde SV, Balen D, Meineke I, Schmidt T, Sehrt D, Sabolic I, Koepsell H, Brockmoller J: The effects of genetic polymorphisms in the organic cation transporters OCT1, OCT2, and OCT3 on the renal clearance of metformin. Clin Pharmacol Ther. 2009 Sep;86(3):299-306. doi: 10.1038/clpt.2009.92. Epub 2009 Jun 17. [PubMed:19536068 ]

Enzyme Details

4. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

References

Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [PubMed:9486191 ]

Enzyme Details

5. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]

Enzyme Details

6. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Lu R, Kanai N, Bao Y, Wolkoff AW, Schuster VL: Regulation of renal oatp mRNA expression by testosterone. Am J Physiol. 1996 Feb;270(2 Pt 2):F332-7. [PubMed:8779895 ]
Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894 ]
Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566 ]

Enzyme Details

7. Solute carrier family 22 member 3

General function:: Involved in transmembrane transport
Specific function:: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:: SLC22A3
Uniprot ID:: O75751
Molecular weight:: 61279.5

References

Tzvetkov MV, Vormfelde SV, Balen D, Meineke I, Schmidt T, Sehrt D, Sabolic I, Koepsell H, Brockmoller J: The effects of genetic polymorphisms in the organic cation transporters OCT1, OCT2, and OCT3 on the renal clearance of metformin. Clin Pharmacol Ther. 2009 Sep;86(3):299-306. doi: 10.1038/clpt.2009.92. Epub 2009 Jun 17. [PubMed:19536068 ]

Enzyme Details

8. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Kobayashi Y, Hirokawa N, Ohshiro N, Sekine T, Sasaki T, Tokuyama S, Endou H, Yamamoto T: Differential gene expression of organic anion transporters in male and female rats. Biochem Biophys Res Commun. 2002 Jan 11;290(1):482-7. [PubMed:11779196 ]

Only showing the first 10 proteins. There are 74 proteins in total.

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Showing metabocard for Testosterone (HMDB0000234)

MOL for HMDB0000234 (Testosterone)

3D MOL for HMDB0000234 (Testosterone)

3D SDF for HMDB0000234 (Testosterone)

3D-SDF for HMDB0000234 (Testosterone)

PDB for HMDB0000234 (Testosterone)

3D PDB for HMDB0000234 (Testosterone)

SMILES for HMDB0000234 (Testosterone)

INCHI for HMDB0000234 (Testosterone)

Structure for HMDB0000234 (Testosterone)

3D Structure for HMDB0000234 (Testosterone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

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GC-MS Spectra

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