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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:04 UTC

HMDB ID

HMDB0000628

Secondary Accession Numbers

HMDB00628

Metabolite 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>
HMDB0000628

> <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-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 View Stereo Labels

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 Molecular Weight

288.4244

Monoisotopic Molecular Weight

288.20893014

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

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 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10468933)

Organ

Gland

Adrenal Gland (HMDB: HMDB0000628)

Cellular substructure

Membrane (HMDB: HMDB0000628)
Extracellular (HMDB: HMDB0000628)

Source

Exogenous

Exogenous (HMDB: HMDB0000628)

Food

Animal origin

Poultry

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000628)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

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	33.93 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.355	31661259
DarkChem	[M-H]-	168.194	31661259
AllCCS	[M+H]+	174.277	32859911
AllCCS	[M-H]-	178.51	32859911
DeepCCS	[M-2H]-	205.288	30932474
DeepCCS	[M+Na]+	179.343	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.1	32859911
AllCCS	[M+Na]+	178.0	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	178.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.97 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1298 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2544.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	427.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	204.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	457.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	634.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	694.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	95.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1305.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	452.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1471.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	424.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	431.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	302.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	469.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	15.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epitestosterone	[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
Epitestosterone	[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
Epitestosterone	[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
Epitestosterone,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
Epitestosterone,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
Epitestosterone,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
Epitestosterone,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
Epitestosterone,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
Epitestosterone,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@@]21C	3021.3	Semi standard non polar	33892256
Epitestosterone,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
Epitestosterone,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
Epitestosterone,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
Epitestosterone,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 - Epitestosterone EI-B (Non-derivatized)	splash10-006t-1940000000-716f44b32e61cf34c7b4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)	splash10-006t-1940000000-716f44b32e61cf34c7b4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (1 TMS)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (2 TMS)	splash10-053u-1920200000-db3504f562c54e6e1bbb	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (1 MEOX; 1 TMS)	splash10-004l-3910000000-356ddfa8ddf8e551278d	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)	splash10-0597-7920000000-dde7fba02fcbcec2d665	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)	splash10-05fs-4920000000-ccd839134de79f179f9e	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)	splash10-00ds-0950000000-c65fc8043083ad93d169	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)	splash10-004i-3910000000-d6ace9b7f8aff4dd46d0	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)	splash10-053u-1920200000-db3504f562c54e6e1bbb	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)	splash10-004l-3910000000-b43cd1ee268a855c8aa0	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)	splash10-004l-3910000000-356ddfa8ddf8e551278d	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-074i-0390000000-09e2a725ebd92c93dc88	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epitestosterone GC-MS (1 TMS) - 70eV, Positive	splash10-000t-1119000000-bf66038b9de80f6b8aab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epitestosterone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epitestosterone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epitestosterone 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	2018-05-25	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0090000000-e1af5f6bcaf571731a2b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-052b-7900000000-581eb9c19ccb29ebac52	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-052b-9300000000-37c235bd069ce0c93813	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone Linear Ion Trap , negative-QTOF	splash10-0690-0190000000-d4814fdc14f2b2818eb2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone Linear Ion Trap , positive-QTOF	splash10-0fk9-1690000000-b39908a52b06c7853085	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone 20V, Positive-QTOF	splash10-0a4r-0950000000-5ee2f8e5795ea913ebad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone 10V, Positive-QTOF	splash10-000i-0190000000-f4e3ff2bfc8e41de9c54	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epitestosterone 40V, Positive-QTOF	splash10-0a4i-0900000000-3b8123363e31bc461acf	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 10V, Positive-QTOF	splash10-00dr-0190000000-4b469479ef097f60ed90	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 20V, Positive-QTOF	splash10-00dr-0390000000-8bebba5f70c72e80b630	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 40V, Positive-QTOF	splash10-0udi-5890000000-46ba5a59d051001f2a63	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 10V, Negative-QTOF	splash10-000i-0090000000-3c963477109db1f6b39e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 20V, Negative-QTOF	splash10-000i-0090000000-87d4a2534cd39e8c54a8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 40V, Negative-QTOF	splash10-0abc-1190000000-abbd0808a06f67c1f6fc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 10V, Negative-QTOF	splash10-000i-0090000000-383f8ad782110ec64fbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 20V, Negative-QTOF	splash10-000i-0090000000-383f8ad782110ec64fbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 40V, Negative-QTOF	splash10-0uy0-0090000000-9f1b0a9f20aee057d1dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 10V, Positive-QTOF	splash10-000i-0090000000-7add27947ecc7b5b14bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 20V, Positive-QTOF	splash10-03ki-0960000000-98c9b1c540f6d162d225	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epitestosterone 40V, Positive-QTOF	splash10-0bt9-2900000000-f5717697f5b4e8b7505f	2021-09-23	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

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Adrenal Gland
Ovary
Prostate
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00132 +/- 0.00008 uM	Adult (>18 years old)	Male	Eugonadism	10468933	details
Blood	Detected and Quantified	0.00068 +/- 0.00004 uM	Adult (>18 years old)	Male	Hypogonadism	10468933	details

Associated Disorders and Diseases

Disease References

Hypogonadism
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 ]

Associated OMIM IDs

146110 (Hypogonadism)

External Links

DrugBank ID

DB07768

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Alvarez, Francisco. Steroids. CCXLIX. A new synthesis of epitestosterone from pregnenolone acetate via nitrosation. Steroids (1963), 2(4), 393-8.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 metabocard for Epitestosterone (HMDB0000628)

MOL for HMDB0000628 (Epitestosterone)

3D MOL for HMDB0000628 (Epitestosterone)

3D SDF for HMDB0000628 (Epitestosterone)

3D-SDF for HMDB0000628 (Epitestosterone)

PDB for HMDB0000628 (Epitestosterone)

3D PDB for HMDB0000628 (Epitestosterone)

SMILES for HMDB0000628 (Epitestosterone)

INCHI for HMDB0000628 (Epitestosterone)

Structure for HMDB0000628 (Epitestosterone)

3D Structure for HMDB0000628 (Epitestosterone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra