NP-MRD: Showing NP-Card for Epitestosterone (NP0000757)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-09 22:33:17 UTC

NP-MRD ID

NP0000757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epitestosterone

Description

Epitestosterone, or isotestosterone, also known as 17alpha-testosterone or as androst-4-en-17alpha-ol-3-one belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. Epitestosterone is an endogenous steroid and a C-17 epimer of the androgen sex hormone testosterone. It is a weak competitive antagonist of the androgen receptor (AR) and a potent 5alpha-reductase inhibitor. Structurally, epitestosterone differs from testosterone only in the configuration at the hydroxy-bearing carbon, C17. Epitestosterone is believed to form in a similar way to testosterone with 50% of epitestosterone production in human males taking place in the testis. Epitestosterone levels are typically highest in young males; however, by adulthood, most healthy males exhibit a testosterone to epitestosterone ratio (T/E ratio) of about 1:1 (PMID: 11901061 ). A study of Australian athletes found that the mean T/E ratio in the study was 1.15:1. Another study found that the max T/E ratio for the 95th percentile of athletes was 3.71:1, And the max T/E ratio for the 99th percentile was 5.25:1. Epitestosterone has not been shown to enhance athletic performance, although administration of epistestosterone can be used to mask a high level of testosterone if the standard T/E ratio test is used. As such, epitestosterone is banned by many sporting authorities as a masking agent for testosterone. Interestingly, small amounts of ethanol can elevate T/E values, with women being more susceptible (PMID: 28671321 ).

Structure

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

HMDB0000628
     RDKit          3D
Epitestosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.4251   -1.1078    0.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3105   -0.5988   -0.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4100   -1.4867   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -1.5244   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -0.1458   -0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    0.7044    0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1931    2.0311    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226    1.7373    1.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    0.8291    1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884    1.0203    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434    0.1812    0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5938    0.0145    1.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223   -0.4553   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217   -0.2449   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961   -0.2370    0.1785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0261   -1.5644    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    0.7916   -0.5067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7375    1.6639   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    1.1449   -0.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6334   -0.3301   -1.0715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6509   -0.6045   -2.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720   -0.3262    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604   -1.7387    0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -1.7532    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -1.1285   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270   -2.5000   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -2.1937    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -1.9567   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.3497   -1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    0.1977    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    2.4476   -0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5828    2.7300    0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625    2.6589    2.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6754    1.1393    2.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686    1.8149    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0115    0.0361   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900   -1.5304   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977   -1.0106   -1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.7476   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -1.5989    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363   -2.4263    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -1.5957    1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.9765   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9578    1.5584    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5709    2.7444   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760    1.2758   -0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9329    1.7288   -1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4290   -0.9125   -0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352   -1.5529   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1
  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  6
  6 30  1  1
  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  6
 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


  Mrv1652305271900112D          

 24 27  0  0  1  0            999 V2000
   23.3972  -11.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3972  -12.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1117  -12.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8261  -12.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8261  -11.4754    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.1117  -11.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5406  -12.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2550  -12.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2550  -11.4754    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.5406  -11.0629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.9695  -11.0629    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.9695  -10.2379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.2550   -9.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5406  -10.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7542  -11.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2391  -10.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7542   -9.9829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6827  -12.7129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0558   -9.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0091   -9.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5406  -11.8879    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.8261  -10.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2550  -10.6504    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.0558  -11.8834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
 12 19  1  1  0  0  0
 17 20  1  6  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000757

> <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-KZYORJDKSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.4244

> <EXACT_MASS>
288.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.92537613065009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14R,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>
19.086860121685625

> <JCHEM_PKA_STRONGEST_BASIC>
-0.883941123357545

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.4298

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000628
     RDKit          3D
Epitestosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.4251   -1.1078    0.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3105   -0.5988   -0.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4100   -1.4867   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -1.5244   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -0.1458   -0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    0.7044    0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1931    2.0311    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226    1.7373    1.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    0.8291    1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884    1.0203    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434    0.1812    0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5938    0.0145    1.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223   -0.4553   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217   -0.2449   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961   -0.2370    0.1785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0261   -1.5644    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    0.7916   -0.5067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7375    1.6639   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    1.1449   -0.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6334   -0.3301   -1.0715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6509   -0.6045   -2.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720   -0.3262    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604   -1.7387    0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -1.7532    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -1.1285   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270   -2.5000   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -2.1937    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -1.9567   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.3497   -1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    0.1977    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    2.4476   -0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5828    2.7300    0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625    2.6589    2.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6754    1.1393    2.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686    1.8149    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0115    0.0361   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900   -1.5304   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977   -1.0106   -1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.7476   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -1.5989    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363   -2.4263    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -1.5957    1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.9765   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9578    1.5584    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5709    2.7444   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760    1.2758   -0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9329    1.7288   -1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4290   -0.9125   -0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352   -1.5529   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1
  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  6
  6 30  1  1
  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  6
 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                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      43.675 -21.421   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      43.675 -22.961   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      45.009 -23.731   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      46.342 -22.961   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.342 -21.421   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      45.009 -20.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.676 -23.731   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.009 -22.961   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.009 -21.421   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.676 -20.651   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.343 -20.651   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      50.343 -19.111   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.009 -18.341   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      47.676 -19.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.808 -21.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      52.713 -19.881   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      51.808 -18.635   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      42.341 -23.731   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      50.504 -17.579   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      52.284 -17.170   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      47.676 -22.191   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      46.342 -19.881   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      49.009 -19.881   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      50.504 -22.182   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20                                                  
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000628
HETATM    1  C1  UNL     1      -2.425  -1.108   0.950  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.311  -0.599  -0.442  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.410  -1.487  -1.270  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.027  -1.524  -0.727  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.545  -0.146  -0.447  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.434   0.704   0.339  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.193   2.031   0.641  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.223   1.737   1.744  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.220   0.829   1.118  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.488   1.020   1.453  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.543   0.181   0.893  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.594   0.015   1.520  1.00  0.00           O  
HETATM   13  C12 UNL     1       4.322  -0.455  -0.429  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.922  -0.245  -0.935  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.896  -0.237   0.178  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.026  -1.564   0.934  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.660   0.792  -0.507  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.737   1.664  -0.017  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.942   1.145  -0.809  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.633  -0.330  -1.071  1.00  0.00           C  
HETATM   21  O2  UNL     1      -3.651  -0.604  -2.438  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.572  -0.326   1.720  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.360  -1.739   0.997  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.613  -1.753   1.291  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.425  -1.129  -2.320  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.827  -2.500  -1.259  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.014  -2.194   0.143  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.635  -1.957  -1.535  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.613   0.350  -1.461  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.648   0.198   1.291  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.708   2.448  -0.248  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.583   2.730   0.999  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.662   2.659   2.121  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.675   1.139   2.501  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.769   1.815   2.159  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.012   0.036  -1.147  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.590  -1.530  -0.406  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.698  -1.011  -1.706  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.826   0.748  -1.454  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.196  -1.599   1.694  1.00  0.00           H  
HETATM   41  H20 UNL     1       2.036  -2.426   0.265  1.00  0.00           H  
HETATM   42  H21 UNL     1       2.959  -1.596   1.528  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.405   0.976  -1.549  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.958   1.558   1.041  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.571   2.744  -0.234  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.876   1.276  -0.255  1.00  0.00           H  
HETATM   47  H26 UNL     1      -3.933   1.729  -1.766  1.00  0.00           H  
HETATM   48  H27 UNL     1      -4.429  -0.912  -0.563  1.00  0.00           H  
HETATM   49  H28 UNL     1      -3.935  -1.553  -2.526  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

HMDB0000628
     RDKit          3D
Epitestosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.4251   -1.1078    0.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3105   -0.5988   -0.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4100   -1.4867   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275   -1.5244   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5445   -0.1458   -0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    0.7044    0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1931    2.0311    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226    1.7373    1.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2203    0.8291    1.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4884    1.0203    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434    0.1812    0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5938    0.0145    1.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223   -0.4553   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217   -0.2449   -0.9350 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961   -0.2370    0.1785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0261   -1.5644    0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    0.7916   -0.5067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7375    1.6639   -0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    1.1449   -0.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6334   -0.3301   -1.0715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6509   -0.6045   -2.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5720   -0.3262    1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3604   -1.7387    0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6130   -1.7532    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4250   -1.1285   -2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8270   -2.5000   -1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0141   -2.1937    0.1429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -1.9567   -1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.3497   -1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    0.1977    1.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082    2.4476   -0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5828    2.7300    0.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625    2.6589    2.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6754    1.1393    2.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686    1.8149    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0115    0.0361   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5900   -1.5304   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977   -1.0106   -1.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.7476   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -1.5989    1.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0363   -2.4263    0.2649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -1.5957    1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.9765   -1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9578    1.5584    1.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5709    2.7444   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8760    1.2758   -0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9329    1.7288   -1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4290   -0.9125   -0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352   -1.5529   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  1
  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  6
  6 30  1  1
  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  6
 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
Epi-testosterone	ChEBI
17-Epitestosterone	HMDB
17a-cis-Testosterone	HMDB
cis-Testosterone	HMDB
Isotestosterone	HMDB
17-alpha-Testosterone	HMDB
17 alpha Testosterone	HMDB
Epitestosterone	MeSH, HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Mass

288.4244 Da

Monoisotopic Mass

288.20893 Da

IUPAC Name

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

CAS Registry Number

481-30-1

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-KZYORJDKSA-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
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
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:42534 )
17alpha-hydroxy steroid (CHEBI:42534 )
androstanoid (CHEBI:42534 )
C19 steroids (androgens) and derivatives (LMST02020051 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

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	33.93 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

HMDB0000628

DrugBank ID

DB07768

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011544

KNApSAcK ID

Not Available

Chemspider ID

9789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epitestosterone

METLIN ID

5601

PubChem Compound

10204

PDB ID

Not Available

ChEBI ID

42534

Good Scents ID

Not Available

References

General References

Falk O, Palonek E, Bjorkhem I: Effect of ethanol on the ratio between testosterone and epitestosterone in urine. Clin Chem. 1988 Jul;34(7):1462-4. [PubMed:3390919 ]
Kicman AT, Oftebro H, Walker C, Norman N, Cowan DA: Potential use of ketoconazole in a dynamic endocrine test to differentiate between biological outliers and testosterone use by athletes. Clin Chem. 1993 Sep;39(9):1798-803. [PubMed:8375050 ]
Riondino G, Strollo F: [Age-dependent changes in epitestosterone urinary excretion in man]. Boll Soc Ital Biol Sper. 1981 Nov 30;57(22):2215-21. [PubMed:7326107 ]
Starka L: Epitestosterone. J Steroid Biochem Mol Biol. 2003 Oct;87(1):27-34. [PubMed:14630088 ]
Marenich LP: [Effect of chorionic gonadotropin on the urinary excretion of testosterone and other androgens in healthy men and those with coronary arteriosclerosis]. Kardiologiia. 1979 Jun;19(6):76-9. [PubMed:156806 ]
Aguilera R, Hatton CK, Catlin DH: Detection of epitestosterone doping by isotope ratio mass spectrometry. Clin Chem. 2002;48(4):629-36. [PubMed:11901061 ]
Bicikova M, Hampl R, Hill M, Starka L: Inhibition of steroid 17 alpha-hydroxylase and C17,20-lyase in the human testis by epitestosterone. J Steroid Biochem Mol Biol. 1993 Oct;46(4):515-8. [PubMed:8217882 ]
Havlikova H, Hill M, Hampl R, Starka L: Sex- and age-related changes in epitestosterone in relation to pregnenolone sulfate and testosterone in normal subjects. J Clin Endocrinol Metab. 2002 May;87(5):2225-31. [PubMed:11994368 ]
Yamamoto Y, Peric-Golia P, Osawa Y, Kirdani RY, Sanberg AA: Androgen metabolism in sheep. Steroids. 1978 Oct;32(3):373-88. [PubMed:715826 ]
Kicman AT, Coutts SB, Cowan DA, Handelsman DJ, Howe CJ, Burring S, Wu FC: Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men--effect of adrenal stimulation and implications for detection of testosterone abuse. Clin Endocrinol (Oxf). 1999 May;50(5):661-8. [PubMed:10468933 ]
Albeiroti S, Ahrens BD, Sobolevskii T, Butch AW: The influence of small doses of ethanol on the urinary testosterone to epitestosterone ratio in men and women. Drug Test Anal. 2018 Mar;10(3):575-583. doi: 10.1002/dta.2241. Epub 2017 Aug 1. [PubMed:28671321 ]

Showing NP-Card for Epitestosterone (NP0000757)

MOL for NP0000757 (Epitestosterone)

3D MOL for NP0000757 (Epitestosterone)

3D SDF for NP0000757 (Epitestosterone)

3D-SDF for NP0000757 (Epitestosterone)

PDB for NP0000757 (Epitestosterone)

3D PDB for NP0000757 (Epitestosterone)

SMILES for NP0000757 (Epitestosterone)

INCHI for NP0000757 (Epitestosterone)

Structure for NP0000757 (Epitestosterone)

3D Structure for NP0000757 (Epitestosterone)