NP-MRD: Showing NP-Card for Testosterone (NP0000552)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:22 UTC

NP-MRD ID

NP0000552

Secondary Accession Numbers

None

Natural Product 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
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   -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
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    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>
NP0000552

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

288.4244 Da

Monoisotopic Mass

288.20893 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Botrytis cinerea	-	KNApSAcK
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Curvularia lunata	LOTUS Database	35616633
Daphnia magna	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Ilybius fenestratus	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Locusta migratoria	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Moschus moschiferus	-	KNApSAcK
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pinus sylvestris	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Vitex agnus-castus	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted 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

External Links

HMDB ID

HMDB0000234

DrugBank ID

DB00624

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Testosterone (NP0000552)

MOL for NP0000552 (Testosterone)

3D MOL for NP0000552 (Testosterone)

3D SDF for NP0000552 (Testosterone)

3D-SDF for NP0000552 (Testosterone)

PDB for NP0000552 (Testosterone)

3D PDB for NP0000552 (Testosterone)

SMILES for NP0000552 (Testosterone)

INCHI for NP0000552 (Testosterone)

Structure for NP0000552 (Testosterone)

3D Structure for NP0000552 (Testosterone)