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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-04-12 20:35:48 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0006027

Secondary Accession Numbers

HMDB06027

Metabolite Identification

Common Name

Oxymesterone

Description

Oxymesterone is an anabolic steroid abused by some athletes and is tested for in regular preventive doping control analysis. Androgenic anabolic steroids (AAS) are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. Oxymesterone and other steroids can be detected in human urine using liquid chromatography/electrospray ionization orthogonal acceleration time-of-flight mass spectrometry (LCoaTOFMS) and gas chromatography/electron ionization orthogonal acceleration time-of-flight mass spectrometry (GCoaTOFMS), using methods that have been developed in order to acquire accurate full scan MS data to be used to detect designer steroids. (PMID: 17610244 , 17667636 , 17723876 , 17723877 , 2079979 , 3308301 , 8456050 , 8674183 , 8725393 , 9216475 ).

Structure

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


  Mrv0541 02231220322D          

 26 29  0  0  1  0            999 V2000
   15.8750   -7.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -6.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8295   -4.4597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8295   -5.2846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -5.6971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4007   -5.2846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6100   -4.2084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -4.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6501   -5.7028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6100   -5.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4007   -4.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0915   -4.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1284   -6.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6435   -6.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3876   -6.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8856   -5.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6564   -4.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1035   -5.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8719   -7.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0967   -6.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8993   -6.1471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.1255   -4.7440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4224   -6.1232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.8663   -3.4243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4300   -4.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9168   -3.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 21  1  6  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 22  1  1  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 23  1  6  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  1  0  0  0
 10 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
  7 24  1  1  0  0  0
  7 25  1  6  0  0  0
  3 26  1  1  0  0  0
M  END

HMDB0006027
     RDKit          3D
Oxymesterone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.6834    0.6864    1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5600    0.4373    0.3623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5238    1.1472   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8131   -1.0574    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.7036    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195   -0.6152    0.5083 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0975   -0.7763    0.1071 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5358   -1.7194    1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -2.1065    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -0.9851   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921   -1.1977   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4905   -2.4277    0.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6517   -0.1210   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428   -0.4037   -1.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    1.2676   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753    1.4151    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300    0.3125   -0.3456 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8826    0.4819   -1.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554    0.5188    0.2285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0446    1.6808   -0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392    1.7960    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.5852   -0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2118    0.4180   -1.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    1.0140    2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    1.4741    2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -0.2384    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8467    1.9409    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611   -1.2516   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3972   -1.4810    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -2.5347    0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317   -2.0950   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -0.4688    1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658   -1.2375   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883   -1.0761    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -2.5442    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.8685   -0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447   -2.5852    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4414   -3.2168   -0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    1.5806    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    1.9094   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0644    1.4794    1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    2.3963   -0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9552   -0.0154   -2.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734    1.5686   -2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162    0.0415   -2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847    0.7709    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261    1.4852   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353    2.5883   -0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708    1.8945    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9496    2.7183   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.0351   -1.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679    1.4237   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258   -0.2708   -2.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  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  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  2  1  0
 22  6  1  0
 19  7  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  1
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  END


  Mrv0541 02231220322D          

 26 29  0  0  1  0            999 V2000
   15.8750   -7.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3807   -6.9776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8295   -4.4597    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.8295   -5.2846    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -5.6971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.4007   -5.2846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6100   -4.2084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1152   -4.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6501   -5.7028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6100   -5.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4007   -4.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0915   -4.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1284   -6.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6435   -6.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3876   -6.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8856   -5.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6564   -4.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1035   -5.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8719   -7.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0967   -6.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8993   -6.1471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.1255   -4.7440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4224   -6.1232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.8663   -3.4243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4300   -4.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9168   -3.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 21  1  6  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 22  1  1  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 23  1  6  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 14  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  1  0  0  0
 10 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
  7 24  1  1  0  0  0
  7 25  1  6  0  0  0
  3 26  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0006027

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h12-14,22-23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

> <INCHI_KEY>
RXXBBHGCAXVBES-XMUHMHRVSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.71217252944716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-6,14-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.127342284666667

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.313190913539229

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5280912870485565

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
91.0354

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxymesterone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006027
     RDKit          3D
Oxymesterone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.6834    0.6864    1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5600    0.4373    0.3623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5238    1.1472   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8131   -1.0574    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.7036    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195   -0.6152    0.5083 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0975   -0.7763    0.1071 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5358   -1.7194    1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -2.1065    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -0.9851   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921   -1.1977   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4905   -2.4277    0.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6517   -0.1210   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428   -0.4037   -1.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    1.2676   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753    1.4151    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300    0.3125   -0.3456 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8826    0.4819   -1.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554    0.5188    0.2285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0446    1.6808   -0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392    1.7960    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.5852   -0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2118    0.4180   -1.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    1.0140    2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    1.4741    2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -0.2384    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8467    1.9409    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611   -1.2516   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3972   -1.4810    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -2.5347    0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317   -2.0950   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -0.4688    1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658   -1.2375   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883   -1.0761    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -2.5442    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.8685   -0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447   -2.5852    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4414   -3.2168   -0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    1.5806    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    1.9094   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0644    1.4794    1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    2.3963   -0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9552   -0.0154   -2.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734    1.5686   -2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162    0.0415   -2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847    0.7709    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261    1.4852   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353    2.5883   -0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708    1.8945    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9496    2.7183   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.0351   -1.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679    1.4237   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258   -0.2708   -2.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  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  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  2  1  0
 22  6  1  0
 19  7  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  1
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      29.633 -14.635   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.844 -13.025   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      35.148  -8.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      35.148  -9.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.815 -10.635   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.481  -9.865   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.605  -7.856   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.815  -7.555   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.080 -10.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.605 -10.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.481  -8.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.504  -9.095   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.840 -12.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.068 -12.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.457 -13.051   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.653  -9.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.092  -9.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.193 -10.590   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.628 -13.095   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.181 -12.260   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      35.279 -11.475   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      33.834  -8.855   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      32.522 -11.430   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0      37.084  -6.392   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      38.136  -7.571   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      35.311  -6.794   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    7    8   26                                             
CONECT    4    3    5   10   21                                             
CONECT    5    4    6   13   22                                             
CONECT    6    5    9   11   23                                             
CONECT    7    3   12   24   25                                             
CONECT    8    3   11                                                       
CONECT    9    6   14   16   17                                             
CONECT   10    4   12                                                       
CONECT   11    6    8                                                       
CONECT   12    7   10                                                       
CONECT   13    5   15                                                       
CONECT   14    9   15   19                                                  
CONECT   15   13   14                                                       
CONECT   16    9   18                                                       
CONECT   17    9                                                            
CONECT   18   16   20                                                       
CONECT   19    1   14   20                                                  
CONECT   20    2   18   19                                                  
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    7                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0006027
HETATM    1  C1  UNL     1      -3.683   0.686   1.835  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.560   0.437   0.362  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.524   1.147  -0.348  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.813  -1.057   0.156  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.439  -1.704   0.095  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.520  -0.615   0.508  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.097  -0.776   0.107  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.536  -1.719   1.142  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.871  -2.106   0.622  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.615  -0.985  -0.009  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.892  -1.198  -0.280  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.490  -2.428   0.022  1.00  0.00           O  
HETATM   13  C11 UNL     1       4.652  -0.121  -0.898  1.00  0.00           C  
HETATM   14  O3  UNL     1       5.543  -0.404  -1.752  1.00  0.00           O  
HETATM   15  C12 UNL     1       4.337   1.268  -0.489  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.975   1.415   0.093  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.030   0.313  -0.346  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.883   0.482  -1.865  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.655   0.519   0.229  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.045   1.681  -0.412  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.439   1.796   0.223  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.184   0.585  -0.171  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.212   0.418  -1.665  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.741   1.014   2.037  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.039   1.474   2.222  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.544  -0.238   2.448  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.847   1.941   0.162  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.361  -1.252  -0.786  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.397  -1.481   0.990  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.355  -2.535   0.824  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.232  -2.095  -0.935  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.584  -0.469   1.593  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.066  -1.237  -0.864  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.688  -1.076   2.052  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.145  -2.544   1.339  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.724  -2.869  -0.187  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.445  -2.585   1.443  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.441  -3.217  -0.608  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.131   1.581   0.252  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.513   1.909  -1.390  1.00  0.00           H  
HETATM   41  H18 UNL     1       3.064   1.479   1.198  1.00  0.00           H  
HETATM   42  H19 UNL     1       2.565   2.396  -0.260  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.955  -0.015  -2.232  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.873   1.569  -2.054  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.716   0.041  -2.414  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.785   0.771   1.310  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.226   1.485  -1.486  1.00  0.00           H  
HETATM   48  H25 UNL     1       0.535   2.588  -0.217  1.00  0.00           H  
HETATM   49  H26 UNL     1      -1.271   1.895   1.295  1.00  0.00           H  
HETATM   50  H27 UNL     1      -1.950   2.718  -0.128  1.00  0.00           H  
HETATM   51  H28 UNL     1      -3.182  -0.035  -1.997  1.00  0.00           H  
HETATM   52  H29 UNL     1      -2.168   1.424  -2.126  1.00  0.00           H  
HETATM   53  H30 UNL     1      -1.426  -0.271  -2.039  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   22
CONECT    3   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   22   32
CONECT    7    8   19   33
CONECT    8    9   34   35
CONECT    9   10   36   37
CONECT   10   11   11   17
CONECT   11   12   13
CONECT   12   38
CONECT   13   14   14   15
CONECT   15   16   39   40
CONECT   16   17   41   42
CONECT   17   18   19
CONECT   18   43   44   45
CONECT   19   20   46
CONECT   20   21   47   48
CONECT   21   22   49   50
CONECT   22   23
CONECT   23   51   52   53
END

HMDB0006027
     RDKit          3D
Oxymesterone
 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.6834    0.6864    1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5600    0.4373    0.3623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5238    1.1472   -0.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8131   -1.0574    0.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.7036    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5195   -0.6152    0.5083 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0975   -0.7763    0.1071 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5358   -1.7194    1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -2.1065    0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -0.9851   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921   -1.1977   -0.2803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4905   -2.4277    0.0216 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6517   -0.1210   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428   -0.4037   -1.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    1.2676   -0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753    1.4151    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300    0.3125   -0.3456 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8826    0.4819   -1.8654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554    0.5188    0.2285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0446    1.6808   -0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392    1.7960    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.5852   -0.1708 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2118    0.4180   -1.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    1.0140    2.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    1.4741    2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -0.2384    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8467    1.9409    0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3611   -1.2516   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3972   -1.4810    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -2.5347    0.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317   -2.0950   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -0.4688    1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0658   -1.2375   -0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883   -1.0761    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -2.5442    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.8685   -0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4447   -2.5852    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4414   -3.2168   -0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1308    1.5806    0.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5127    1.9094   -1.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0644    1.4794    1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    2.3963   -0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9552   -0.0154   -2.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734    1.5686   -2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7162    0.0415   -2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7847    0.7709    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2261    1.4852   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353    2.5883   -0.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708    1.8945    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9496    2.7183   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.0351   -1.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679    1.4237   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258   -0.2708   -2.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  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  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  2  1  0
 22  6  1  0
 19  7  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  1
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  1
 20 47  1  0
 20 48  1  0
 21 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,17beta-Dihydroxy-17alpha-methylandrost-4-en-3-one	Kegg
4-Hydroxy-17alpha-methyltestosterone	Kegg
4,17b-Dihydroxy-17a-methylandrost-4-en-3-one	Generator
4,17Β-dihydroxy-17α-methylandrost-4-en-3-one	Generator
4-Hydroxy-17a-methyltestosterone	Generator
4-Hydroxy-17α-methyltestosterone	Generator
17Alpah-methyl-4, 17beta-dihydroxy-androst-4-ene-3-one	MeSH
(17b)- 4,17b-Dihydroxy-17-methyl-androst-4-en-3-one	HMDB
4,17b-Dihydroxy-17-methyl-androst-4-en-3-one	HMDB
4,17b-Dihydroxy-17-methylandrost-4-en-3-one	HMDB
4-Hydroxy-17-methyltestosterone	HMDB
Anamidol	HMDB
Aranabol	HMDB
Oranabol	HMDB
Oxymestrone	HMDB
Theranabol	HMDB
Oxymesterone	KEGG

Chemical Formula

C₂₀H₃₀O₃

Average Molecular Weight

318.4504

Monoisotopic Molecular Weight

318.219494826

IUPAC Name

(1S,2R,10R,11S,14S,15S)-6,14-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

oxymesterone

CAS Registry Number

145-12-0

SMILES

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

InChI Identifier

InChI=1S/C20H30O3/c1-18-9-8-16(21)17(22)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h12-14,22-23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1

InChI Key

RXXBBHGCAXVBES-XMUHMHRVSA-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
4-hydroxysteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Ketone
Cyclic ketone
Enol
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:34903 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0006027)
Cell membrane (HMDB: HMDB0006027)

Biofluid or Excreta

Urine (HMDB: HMDB0006027)

Tissue substructure

Hepatic tissue (HMDB: HMDB0006027)

Cellular substructure

Extracellular (HMDB: HMDB0006027)
Membrane (HMDB: HMDB0006027)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006027)

Source

Exogenous

Food

Food (HMDB: HMDB0006027)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0006027)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0006027)

Cellular process

Cell signaling (HMDB: HMDB0006027)

System process

Reproduction (HMDB: HMDB0006027)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0006027)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006027)

Molecular messenger

Hormone (HMDB: HMDB0006027)

Industrial application

Emulsifier (HMDB: HMDB0006027)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006027)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 °C	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	0.057 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.13	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.04 m³·mol⁻¹	ChemAxon
Polarizability	36.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	207.834	30932474
DeepCCS	[M+Na]+	182.072	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	177.1	32859911
AllCCS	[M+NH4]+	182.7	32859911
AllCCS	[M+Na]+	183.5	32859911
AllCCS	[M-H]-	185.4	32859911
AllCCS	[M+Na-2H]-	185.7	32859911
AllCCS	[M+HCOO]-	186.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxymesterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C	3483.1	Standard polar	33892256
Oxymesterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C	2556.4	Standard non polar	33892256
Oxymesterone	[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C	2802.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxymesterone,1TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	2821.9	Semi standard non polar	33892256
Oxymesterone,1TMS,isomer #2	C[C@]1(O)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	2837.2	Semi standard non polar	33892256
Oxymesterone,1TMS,isomer #3	C[C@]1(O)CC[C@H]2[C@@H]3CCC4=C(O)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2773.5	Semi standard non polar	33892256
Oxymesterone,2TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	2835.0	Semi standard non polar	33892256
Oxymesterone,2TMS,isomer #2	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2816.1	Semi standard non polar	33892256
Oxymesterone,2TMS,isomer #3	C[C@]1(O)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2779.2	Semi standard non polar	33892256
Oxymesterone,3TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2756.9	Semi standard non polar	33892256
Oxymesterone,3TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2866.7	Standard non polar	33892256
Oxymesterone,3TMS,isomer #1	C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3006.7	Standard polar	33892256
Oxymesterone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@]1(C)CC[C@H]2[C@@H]3CCC4=C(O)C(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3067.6	Semi standard non polar	33892256
Oxymesterone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C2CC[C@H]3[C@@H]4CC[C@](C)(O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CCC1=O	3077.9	Semi standard non polar	33892256
Oxymesterone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O)CC[C@H]1[C@@H]3CC[C@](C)(O)[C@@]3(C)CC[C@@H]12	3041.0	Semi standard non polar	33892256
Oxymesterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2CC[C@H]3[C@@H]4CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CCC1=O	3305.0	Semi standard non polar	33892256
Oxymesterone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3320.7	Semi standard non polar	33892256
Oxymesterone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O)[C@@]3(C)CC[C@@H]12	3240.9	Semi standard non polar	33892256
Oxymesterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3448.7	Semi standard non polar	33892256
Oxymesterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3321.3	Standard non polar	33892256
Oxymesterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1O[Si](C)(C)C(C)(C)C)CC[C@H]1[C@@H]3CC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3305.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxymesterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w2l-0192000000-c77a5a7f23ff006d9beb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxymesterone GC-MS (2 TMS) - 70eV, Positive	splash10-0002-1015900000-9a5c2150ebe81a2b37e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxymesterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 10V, Positive-QTOF	splash10-0uxr-0019000000-037f1c6e9e4af67115cc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 20V, Positive-QTOF	splash10-0uxr-0395000000-ac27272e013004d3c409	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 40V, Positive-QTOF	splash10-0fri-6590000000-3f66aaa1c358f70406b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 10V, Negative-QTOF	splash10-014i-0029000000-9dfed808b489b6475143	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 20V, Negative-QTOF	splash10-014i-0059000000-87583a19ad53286aa103	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 40V, Negative-QTOF	splash10-0ukd-2092000000-00f7e9d4636c3a765f9f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 10V, Negative-QTOF	splash10-014i-0009000000-062ad2a35e11d303cf23	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 20V, Negative-QTOF	splash10-014i-0019000000-c475af61b990b381eca5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 40V, Negative-QTOF	splash10-015i-0093000000-05b135598734362e0fa1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 10V, Positive-QTOF	splash10-0gb9-0019000000-62110441f5c1bc055100	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 20V, Positive-QTOF	splash10-01rl-1971000000-767ae77519d3526768de	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymesterone 40V, Positive-QTOF	splash10-0006-1920000000-e669bfd6083f9462e7a3	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023806

KNApSAcK ID

Not Available

Chemspider ID

65047

KEGG Compound ID

C14665

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxymesterone

METLIN ID

Not Available

PubChem Compound

72061

PDB ID

Not Available

ChEBI ID

34903

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Georgakopoulos CG, Vonaparti A, Stamou M, Kiousi P, Lyris E, Angelis YS, Tsoupras G, Wuest B, Nielen MW, Panderi I, Koupparis M: Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids. Rapid Commun Mass Spectrom. 2007;21(15):2439-46. [PubMed:17610244 ]
Furlanello F, Serdoz LV, Cappato R, De Ambroggi L: Illicit drugs and cardiac arrhythmias in athletes. Eur J Cardiovasc Prev Rehabil. 2007 Aug;14(4):487-94. [PubMed:17667636 ]
Kerr JM, Congeni JA: Anabolic-androgenic steroids: use and abuse in pediatric patients. Pediatr Clin North Am. 2007 Aug;54(4):771-85, xii. [PubMed:17723876 ]
Smurawa TM, Congeni JA: Testosterone precursors: use and abuse in pediatric athletes. Pediatr Clin North Am. 2007 Aug;54(4):787-96, xii. [PubMed:17723877 ]
Yesalis CE, Anderson WA, Buckley WE, Wright JE: Incidence of the nonmedical use of anabolic-androgenic steroids. NIDA Res Monogr. 1990;102:97-112. [PubMed:2079979 ]
Hatton CK, Catlin DH: Detection of androgenic anabolic steroids in urine. Clin Lab Med. 1987 Sep;7(3):655-68. [PubMed:3308301 ]
Brower KJ: Anabolic steroids. Psychiatr Clin North Am. 1993 Mar;16(1):97-103. [PubMed:8456050 ]
Schanzer W: Metabolism of anabolic androgenic steroids. Clin Chem. 1996 Jul;42(7):1001-20. [PubMed:8674183 ]
Lukas SE: CNS effects and abuse liability of anabolic-androgenic steroids. Annu Rev Pharmacol Toxicol. 1996;36:333-57. [PubMed:8725393 ]
Catlin DH, Hatton CK, Starcevic SH: Issues in detecting abuse of xenobiotic anabolic steroids and testosterone by analysis of athletes' urine. Clin Chem. 1997 Jul;43(7):1280-8. [PubMed:9216475 ]

Showing metabocard for Oxymesterone (HMDB0006027)

MOL for HMDB0006027 (Oxymesterone)

3D MOL for HMDB0006027 (Oxymesterone)

3D SDF for HMDB0006027 (Oxymesterone)

3D-SDF for HMDB0006027 (Oxymesterone)

PDB for HMDB0006027 (Oxymesterone)

3D PDB for HMDB0006027 (Oxymesterone)

SMILES for HMDB0006027 (Oxymesterone)

INCHI for HMDB0006027 (Oxymesterone)

Structure for HMDB0006027 (Oxymesterone)

3D Structure for HMDB0006027 (Oxymesterone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra