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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-04-12 20:54:27 UTC

Update Date

2022-09-22 18:34:18 UTC

HMDB ID

HMDB0006036

Secondary Accession Numbers

HMDB06036

Metabolite Identification

Common Name

Mesterolone

Description

Mesterolone is a synthetic anabolic androgenic steroid (AAS) with reported abuses in human sports. As for other AAS, mesterolone is also a potential doping agent in equine sports. In humans, mesterolone exhibits no inhibitory effects on hypophysial gonadotropin secretion or on spermatogenesis, unlike most androgens. Mesterolone has been used in the treatment of primary nocturnal enuresis in boys six to ten years of age. Mesterolone probably modulates the autonomic innervation of the vesical musculature with correction of the defective neural mechanism which is believed to be implicated in the pathogenesis of nocturnal enuresis. Mesterolone has been utilized in hypogonadism patients to increase total ejaculation volume and the concentration of fructose in the spermatic plasma to normal levels. Mesterolone treatment decreases cholesterol, beta-lipoproteins, fatty acid esters, free fatty acids, triglycerides and glycerol in human serum. (PMID: 4880965 , 17616252 , 10796496 , 17636603 , 2087834 , 6111418 , 6142498 , 6386424 , 7558381 , 792898 ).

Structure

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


  Mrv0541 02231220322D          

 26 29  0  0  1  0            999 V2000
   19.9901   -3.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5045   -6.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5244   -5.0808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2389   -5.4932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7738   -5.4988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9532   -5.0808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9532   -4.2559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7672   -6.3580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5244   -4.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2389   -3.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2521   -6.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7338   -5.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7338   -4.0044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0093   -5.0334    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5113   -6.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2152   -4.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7801   -4.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9956   -6.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9532   -3.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2273   -5.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2204   -6.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0252   -4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5599   -5.9469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2629   -4.6776    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0231   -5.9844    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7697   -7.0179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  1  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 23  1  6  0  0  0
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  4 24  1  1  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 17  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 25  1  6  0  0  0
  7 10  1  0  0  0  0
  7 13  1  0  0  0  0
  7 19  1  1  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  8 26  1  6  0  0  0
  9 10  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 16  1  0  0  0  0
 14 20  1  0  0  0  0
 14 22  1  6  0  0  0
 18 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END

HMDB0006036
     RDKit          3D
Mesterolone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.3548    1.5858    1.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    0.2244    1.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8162   -0.1708    1.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748    0.2246   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5037    0.6726   -0.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5549    0.0823   -1.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157    0.7495   -1.1386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3972    0.7158   -2.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0589    0.9716   -2.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    0.2160   -1.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0084    0.3816   -0.7293 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0210    0.0786   -1.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894   -0.1281   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322   -0.2185    0.5358 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5358   -1.2051    1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3830   -0.6493    0.3428 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4162   -2.0432   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332   -0.5408    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046    0.5567    1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051    0.7003    0.1796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5446    0.0770    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5082   -1.4083   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316    2.1225    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064    1.4700    3.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5595    2.2459    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.5299    2.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -1.2718    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4162    0.3236    1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4336   -0.9735   -1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762    0.6276   -2.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    1.7958   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5603   -0.2440   -2.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8006    1.5044   -3.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240    2.0560   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5720    0.5805   -3.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811   -0.8565   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684    1.3693   -0.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829    0.8944   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.8241   -2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519   -1.0104   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9065    0.7810   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8927    0.7701    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685   -0.8667    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6829   -2.7001    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -2.2125   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -2.4339   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048   -0.3046    2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -1.4879    1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1944    0.4113    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    1.5064    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    1.8106    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -1.9418    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -1.5787   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4589   -1.9060    0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21  2  1  0
 21  7  1  0
 20 10  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 22 52  1  0
 22 53  1  0
 22 54  1  0
M  END


  Mrv0541 02231220322D          

 26 29  0  0  1  0            999 V2000
   19.9901   -3.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5045   -6.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5244   -5.0808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2389   -5.4932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7738   -5.4988    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9532   -5.0808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9532   -4.2559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7672   -6.3580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5244   -4.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2389   -3.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2521   -6.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7338   -5.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7338   -4.0044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0093   -5.0334    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5113   -6.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2152   -4.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7801   -4.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9956   -6.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9532   -3.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2273   -5.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2204   -6.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0252   -4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5599   -5.9469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2629   -4.6776    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0231   -5.9844    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7697   -7.0179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  1  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 23  1  6  0  0  0
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  4 24  1  1  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 17  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 25  1  6  0  0  0
  7 10  1  0  0  0  0
  7 13  1  0  0  0  0
  7 19  1  1  0  0  0
  8 15  1  0  0  0  0
  8 18  1  0  0  0  0
  8 26  1  6  0  0  0
  9 10  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 16  1  0  0  0  0
 14 20  1  0  0  0  0
 14 22  1  6  0  0  0
 18 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006036

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1

> <INCHI_KEY>
UXYRZJKIQKRJCF-TZPFWLJSSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.4669

> <EXACT_MASS>
304.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.457309177771386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.6982767290000007

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.37770535623561

> <JCHEM_PKA_STRONGEST_BASIC>
-0.883991531283366

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
88.15169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
proviron

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006036
     RDKit          3D
Mesterolone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.3548    1.5858    1.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    0.2244    1.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8162   -0.1708    1.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748    0.2246   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5037    0.6726   -0.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5549    0.0823   -1.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157    0.7495   -1.1386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3972    0.7158   -2.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0589    0.9716   -2.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    0.2160   -1.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0084    0.3816   -0.7293 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0210    0.0786   -1.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894   -0.1281   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322   -0.2185    0.5358 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5358   -1.2051    1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3830   -0.6493    0.3428 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4162   -2.0432   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332   -0.5408    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046    0.5567    1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051    0.7003    0.1796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5446    0.0770    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5082   -1.4083   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316    2.1225    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064    1.4700    3.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5595    2.2459    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.5299    2.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -1.2718    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4162    0.3236    1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4336   -0.9735   -1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762    0.6276   -2.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    1.7958   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5603   -0.2440   -2.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8006    1.5044   -3.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240    2.0560   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5720    0.5805   -3.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811   -0.8565   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684    1.3693   -0.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829    0.8944   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.8241   -2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519   -1.0104   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9065    0.7810   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8927    0.7701    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685   -0.8667    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6829   -2.7001    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -2.2125   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -2.4339   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048   -0.3046    2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -1.4879    1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1944    0.4113    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    1.5064    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    1.8106    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -1.9418    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -1.5787   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4589   -1.9060    0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21  2  1  0
 21  7  1  0
 20 10  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 22 52  1  0
 22 53  1  0
 22 54  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      37.315  -6.011   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.075 -12.644   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      32.712  -9.484   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.046 -10.254   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.311 -10.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.379  -9.484   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.379  -7.944   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.299 -11.868   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.712  -7.944   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.046  -7.174   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.071 -11.858   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.836  -9.953   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.836  -7.475   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.884  -9.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.688 -12.670   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.735  -8.714   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.323  -8.725   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.858 -12.715   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.379  -6.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.424 -10.209   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.411 -11.879   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.914  -7.856   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      32.778 -11.101   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      34.091  -8.732   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      35.510 -11.171   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      31.303 -13.100   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   21                                                            
CONECT    3    4    5    9   23                                             
CONECT    4    3    6   11   24                                             
CONECT    5    3    8   14   17                                             
CONECT    6    4    7   12   25                                             
CONECT    7    6   10   13   19                                             
CONECT    8    5   15   18   26                                             
CONECT    9    3   10                                                       
CONECT   10    7    9                                                       
CONECT   11    4   15                                                       
CONECT   12    6   16                                                       
CONECT   13    1    7   16                                                  
CONECT   14    5   20   22                                                  
CONECT   15    8   11                                                       
CONECT   16   12   13                                                       
CONECT   17    5                                                            
CONECT   18    8   21                                                       
CONECT   19    7                                                            
CONECT   20   14   21                                                       
CONECT   21    2   18   20                                                  
CONECT   22   14                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    6                                                            
CONECT   26    8                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0006036
HETATM    1  C1  UNL     1      -2.355   1.586   1.909  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.383   0.224   1.299  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.816  -0.171   1.084  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.375   0.225  -0.212  1.00  0.00           C  
HETATM    5  O1  UNL     1      -5.504   0.673  -0.323  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.555   0.082  -1.440  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.216   0.750  -1.139  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.397   0.716  -2.360  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.059   0.972  -2.214  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.588   0.216  -1.035  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.008   0.382  -0.729  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.021   0.079  -1.756  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.289  -0.128  -0.917  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.832  -0.219   0.536  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.536  -1.205   1.220  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.383  -0.649   0.343  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.416  -2.043  -0.187  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.533  -0.541   1.541  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.505   0.557   1.458  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.205   0.700   0.180  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.545   0.077   0.064  1.00  0.00           C  
HETATM   22  C20 UNL     1      -1.508  -1.408  -0.272  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.332   2.122   1.736  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.306   1.470   3.026  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.559   2.246   1.584  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.977  -0.530   2.038  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.990  -1.272   1.271  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.416   0.324   1.905  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.434  -0.974  -1.744  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.976   0.628  -2.304  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.455   1.796  -0.854  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.560  -0.244  -2.920  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.801   1.504  -3.062  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.324   2.056  -2.181  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.572   0.581  -3.136  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.381  -0.857  -1.243  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.268   1.369  -0.266  1.00  0.00           H  
HETATM   38  H16 UNL     1       3.183   0.894  -2.505  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.779  -0.824  -2.351  1.00  0.00           H  
HETATM   40  H18 UNL     1       4.852  -1.010  -1.225  1.00  0.00           H  
HETATM   41  H19 UNL     1       4.906   0.781  -1.055  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.893   0.770   1.030  1.00  0.00           H  
HETATM   43  H21 UNL     1       4.868  -0.867   2.084  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.683  -2.700   0.683  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.231  -2.213  -0.927  1.00  0.00           H  
HETATM   46  H24 UNL     1       1.490  -2.434  -0.595  1.00  0.00           H  
HETATM   47  H25 UNL     1       2.205  -0.305   2.419  1.00  0.00           H  
HETATM   48  H26 UNL     1       1.021  -1.488   1.848  1.00  0.00           H  
HETATM   49  H27 UNL     1      -0.194   0.411   2.310  1.00  0.00           H  
HETATM   50  H28 UNL     1       1.062   1.506   1.723  1.00  0.00           H  
HETATM   51  H29 UNL     1      -0.352   1.811   0.003  1.00  0.00           H  
HETATM   52  H30 UNL     1      -0.700  -1.942   0.243  1.00  0.00           H  
HETATM   53  H31 UNL     1      -1.520  -1.579  -1.379  1.00  0.00           H  
HETATM   54  H32 UNL     1      -2.459  -1.906   0.084  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   21   26
CONECT    3    4   27   28
CONECT    4    5    5    6
CONECT    6    7   29   30
CONECT    7    8   21   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   20   36
CONECT   11   12   16   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   16   42
CONECT   15   43
CONECT   16   17   18
CONECT   17   44   45   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51
CONECT   21   22
CONECT   22   52   53   54
END

HMDB0006036
     RDKit          3D
Mesterolone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.3548    1.5858    1.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    0.2244    1.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8162   -0.1708    1.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3748    0.2246   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5037    0.6726   -0.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5549    0.0823   -1.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157    0.7495   -1.1386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3972    0.7158   -2.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0589    0.9716   -2.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    0.2160   -1.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0084    0.3816   -0.7293 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0210    0.0786   -1.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894   -0.1281   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322   -0.2185    0.5358 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5358   -1.2051    1.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3830   -0.6493    0.3428 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4162   -2.0432   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332   -0.5408    1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5046    0.5567    1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051    0.7003    0.1796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5446    0.0770    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5082   -1.4083   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316    2.1225    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064    1.4700    3.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5595    2.2459    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -0.5299    2.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9899   -1.2718    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4162    0.3236    1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4336   -0.9735   -1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9762    0.6276   -2.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    1.7958   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5603   -0.2440   -2.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8006    1.5044   -3.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3240    2.0560   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5720    0.5805   -3.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3811   -0.8565   -1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684    1.3693   -0.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829    0.8944   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794   -0.8241   -2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8519   -1.0104   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9065    0.7810   -1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8927    0.7701    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8685   -0.8667    2.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6829   -2.7001    0.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -2.2125   -0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -2.4339   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048   -0.3046    2.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -1.4879    1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1944    0.4113    2.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0615    1.5064    1.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    1.8106    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997   -1.9418    0.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -1.5787   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4589   -1.9060    0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21  2  1  0
 21  7  1  0
 20 10  1  0
 16 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  3 27  1  0
  3 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  1
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 22 52  1  0
 22 53  1  0
 22 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Proviron	MeSH
Vistimon	MeSH
SH-723Mesterolone	ChEMBL, HMDB
(1a,5a,17b)-17-Hydroxy-1-methyl-androstan-3-one	HMDB
17b-Hydroxy-1a-methyl-5a-androstan-3-one	HMDB
1a-Methyl-17b-hydroxy-5a-androstan-3-one	HMDB
1a-Methyl-5a-androstan-17b-ol-3-one	HMDB
1a-Methyl-5a-dihydrotestosterone	HMDB
Androviron	HMDB
Mesteranum	HMDB
Mestoranum	HMDB
Provirone 25	HMDB
SH 723	HMDB
Testiwop	HMDB
Jenapharm brand OF mesterolone	MeSH, HMDB
Schering brand OF mesterolone	MeSH, HMDB
Mesterolone jenapharm brand	MeSH, HMDB
Mesterolone schering brand	MeSH, HMDB

Chemical Formula

C₂₀H₃₂O₂

Average Molecular Weight

304.4669

Monoisotopic Molecular Weight

304.240230268

IUPAC Name

(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

proviron

CAS Registry Number

1424-00-6

SMILES

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

InChI Identifier

InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1

InChI Key

UXYRZJKIQKRJCF-TZPFWLJSSA-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-oxosteroid
3-oxo-5-alpha-steroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C19 steroids (androgens) and derivatives (LMST02020107 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006036)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0006036)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006036)

Source

Exogenous

Exogenous (HMDB: HMDB0006036)

Food

Food (HMDB: HMDB0006036)

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)

Endogenous

Endogenous (HMDB: HMDB0006036)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006036)

Molecular messenger

Hormone (HMDB: HMDB0006036)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006036)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0006036)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	204 °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	0.0064 g/L	ALOGPS
logP	3.75	ALOGPS
logP	3.7	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.38	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	88.15 m³·mol⁻¹	ChemAxon
Polarizability	36.46 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]+	173.414	31661259
DarkChem	[M-H]-	171.846	31661259
DeepCCS	[M-2H]-	206.532	30932474
DeepCCS	[M+Na]+	181.028	30932474
AllCCS	[M+H]+	178.4	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	181.1	32859911
AllCCS	[M+Na]+	181.8	32859911
AllCCS	[M-H]-	182.1	32859911
AllCCS	[M+Na-2H]-	182.5	32859911
AllCCS	[M+HCOO]-	183.0	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.	6.79 minutes	32390414
Predicted by Siyang on May 30, 2022	17.0226 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2716.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	448.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	218.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	509.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	709.6 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	748.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1317.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	491.9 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	1567.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	243.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	425.0 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	11.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mesterolone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C[C@H](C)[C@]12C	2847.7	Standard polar	33892256
Mesterolone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C[C@H](C)[C@]12C	2532.9	Standard non polar	33892256
Mesterolone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C[C@H](C)[C@]12C	2731.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mesterolone,1TMS,isomer #1	C[C@H]1CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2678.0	Semi standard non polar	33892256
Mesterolone,1TMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C	2610.2	Semi standard non polar	33892256
Mesterolone,1TMS,isomer #3	C[C@H]1CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C	2627.9	Semi standard non polar	33892256
Mesterolone,2TMS,isomer #1	C[C@H]1CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2652.8	Semi standard non polar	33892256
Mesterolone,2TMS,isomer #1	C[C@H]1CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2684.4	Standard non polar	33892256
Mesterolone,2TMS,isomer #1	C[C@H]1CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2943.8	Standard polar	33892256
Mesterolone,2TMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2632.5	Semi standard non polar	33892256
Mesterolone,2TMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2662.4	Standard non polar	33892256
Mesterolone,2TMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2947.5	Standard polar	33892256
Mesterolone,1TBDMS,isomer #1	C[C@H]1CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	2925.2	Semi standard non polar	33892256
Mesterolone,1TBDMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C	2846.7	Semi standard non polar	33892256
Mesterolone,1TBDMS,isomer #3	C[C@H]1CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C	2862.5	Semi standard non polar	33892256
Mesterolone,2TBDMS,isomer #1	C[C@H]1CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	3183.8	Semi standard non polar	33892256
Mesterolone,2TBDMS,isomer #1	C[C@H]1CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	3136.0	Standard non polar	33892256
Mesterolone,2TBDMS,isomer #1	C[C@H]1CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	3190.7	Standard polar	33892256
Mesterolone,2TBDMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	3157.8	Semi standard non polar	33892256
Mesterolone,2TBDMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	3129.9	Standard non polar	33892256
Mesterolone,2TBDMS,isomer #2	C[C@H]1C=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C	3193.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mesterolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g1-0290000000-6711f2fd4cedd8b8ebe9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesterolone GC-MS (1 TMS) - 70eV, Positive	splash10-03dj-2029000000-d49394c5377c1d882480	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesterolone 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 - Mesterolone 10V, Positive-QTOF	splash10-052r-0195000000-44dcd42d89336ba3b750	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 20V, Positive-QTOF	splash10-052r-0291000000-412b4cbbe59f184a654f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 40V, Positive-QTOF	splash10-052o-1790000000-09c00b6e9a55d7df2300	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 10V, Negative-QTOF	splash10-0udi-0029000000-e48e22f298cdef547931	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 20V, Negative-QTOF	splash10-0udi-0059000000-231f9da9a32e84b9b604	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 40V, Negative-QTOF	splash10-007c-3090000000-69a7d162e0bb3918d70b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 10V, Negative-QTOF	splash10-0udi-0009000000-f9d10b76ade80bd401ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 20V, Negative-QTOF	splash10-0udi-0009000000-f9d10b76ade80bd401ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 40V, Negative-QTOF	splash10-0udj-0094000000-7cb92f7f18ba37686418	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 10V, Positive-QTOF	splash10-0a4i-0079000000-2860312a6cf9370e1957	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 20V, Positive-QTOF	splash10-0a4r-0960000000-9c3e64e51c3a7c290a00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesterolone 40V, Positive-QTOF	splash10-0a4i-3910000000-a9991caf02a89a982090	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13587

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023812

KNApSAcK ID

Not Available

Chemspider ID

14296

KEGG Compound ID

D04947

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mesterolone

METLIN ID

Not Available

PubChem Compound

15020

PDB ID

Not Available

ChEBI ID

529213

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

Petry R, Rausch-Stroomann JG, Hienz HA, Senge T, Mauss J: Androgen treatment without inhibiting effect on hypophysis and male gonads. Biochemical and morphological studies after treatment with Mesterolone. Acta Endocrinol (Copenh). 1968 Nov;59(3):497-507. [PubMed:4880965 ]
Ho EN, Leung DK, Leung GN, Wan TS, Wong HN, Xu X, Yeung JH: Metabolic studies of mesterolone in horses. Anal Chim Acta. 2007 Jul 16;596(1):149-55. Epub 2007 Jun 3. [PubMed:17616252 ]
Vandekerckhove P, Lilford R, Vail A, Hughes E: Androgens versus placebo or no treatment for idiopathic oligo/asthenospermia. Cochrane Database Syst Rev. 2000;(2):CD000150. [PubMed:10796496 ]
Vandekerckhove P, Lilford R, Vail A, Hughes E: WITHDRAWN: Androgens versus placebo or no treatment for idiopathic oligo/asthenospermia. Cochrane Database Syst Rev. 2007 Jul 18;(4):CD000150. [PubMed:17636603 ]
Schell H: [Objective assessment of therapeutic hair growth--methods, possibilities and problems]. Z Hautkr. 1990 Dec;65(12):1080-4. [PubMed:2087834 ]
Cooper AJ: Short-term treatment in sexual dysfunction: a review. Compr Psychiatry. 1981 Mar-Apr;22(2):206-17. [PubMed:6111418 ]
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Showing metabocard for Mesterolone (HMDB0006036)

MOL for HMDB0006036 (Mesterolone)

3D MOL for HMDB0006036 (Mesterolone)

3D SDF for HMDB0006036 (Mesterolone)

3D-SDF for HMDB0006036 (Mesterolone)

PDB for HMDB0006036 (Mesterolone)

3D PDB for HMDB0006036 (Mesterolone)

SMILES for HMDB0006036 (Mesterolone)

INCHI for HMDB0006036 (Mesterolone)

Structure for HMDB0006036 (Mesterolone)

3D Structure for HMDB0006036 (Mesterolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra