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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015119

Secondary Accession Numbers

HMDB15119

Metabolite Identification

Common Name

Nandrolone phenpropionate

Description

Nandrolone phenpropionate is only found in individuals that have used or taken this drug. It is a C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedule III drug in the U.S. Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.

Structure

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


  Mrv1652305171817152D          

 34 38  0  0  0  0            999 V2000
   -1.6235    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0525   -1.4441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.2066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9090    0.6183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344   -0.6191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    0.2059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1946   -0.6191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.2066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5199    0.6183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344    0.2059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2344    1.0309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0190   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191    2.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    1.2858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7336    2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    3.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480    2.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625    2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8770    2.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8770    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3058    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3058    2.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 10  1  1  0  0  0  0
  2  8  1  0  0  0  0
  8  3  1  0  0  0  0
  3 12  2  0  0  0  0
 10 15  1  0  0  0  0
 12 10  1  0  0  0  0
 12  4  1  0  0  0  0
  4  5  1  0  0  0  0
 17  5  1  0  0  0  0
 17 19  1  0  0  0  0
 15 17  1  0  0  0  0
 15  7  1  0  0  0  0
  6  7  1  0  0  0  0
 20  6  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  1  0  0  0
 19 14  1  6  0  0  0
 20 13  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 24 23  1  1  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 24 20  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 30 34  1  0  0  0  0
M  END

HMDB0015119
     RDKit          3D
Nandrolone phenpropionate
 64 68  0  0  0  0  0  0  0  0999 V2000
   -0.1715    0.7429    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169   -0.0775    0.0958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8053    0.7413   -1.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    1.3283   -0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1386    0.1942   -0.4315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4855    0.7146   -0.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9621    1.8271   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3765    2.2191   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1486    1.1693    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1901    1.4211    0.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7024   -0.2072   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4206   -0.4629   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -1.8088   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854   -1.9766    0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842   -0.7626    0.6559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3152   -1.2130    0.3259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6149   -1.9522    1.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -1.8807    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9057   -0.9005   -0.1660 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1221   -0.2056   -0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -0.4086   -1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -1.1704   -2.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147    0.2944   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1395   -0.3840   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    0.1124   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5321   -0.4815   -0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8355   -0.0077   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168    1.0507    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889    1.6344    0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7808    1.1612    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1008    1.8196    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    0.6115    2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7547    0.4411    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179    1.5809   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134    0.1156   -1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054    1.9556   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    1.9025    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658   -0.3851   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4953    1.0744    0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3256    2.7201   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7642    1.6226   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4801    3.1530   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9238    2.4477   -1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3773   -1.0532   -0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5472   -2.6069    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6304   -2.0196   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -2.2962    1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -2.8848    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661   -0.3325    1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017   -1.8381   -0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716   -1.3902    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -2.9908    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -2.8739    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -1.4771    1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418   -1.5057   -1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.1086   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    1.3682   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889   -0.1934    0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280   -1.4703   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3006   -1.3033   -1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6344   -0.4791   -1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1525    1.3802    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2915    2.4690    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    1.6182    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 16  2  1  0
 30 25  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  1
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  6
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  6
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  0
M  END


  Mrv1652305171817152D          

 34 38  0  0  0  0            999 V2000
   -1.6235    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -1.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199    1.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0525   -1.4441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.2066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9090    0.6183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344    1.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344   -0.6191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946    0.2059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1946   -0.6191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5199   -0.2066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5199    0.6183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344    0.2059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2344    1.0309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0190   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191    2.1107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    1.2858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7336    2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7336    3.3483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4480    2.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625    2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8770    2.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    2.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8770    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3058    1.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3058    2.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 10  1  1  0  0  0  0
  2  8  1  0  0  0  0
  8  3  1  0  0  0  0
  3 12  2  0  0  0  0
 10 15  1  0  0  0  0
 12 10  1  0  0  0  0
 12  4  1  0  0  0  0
  4  5  1  0  0  0  0
 17  5  1  0  0  0  0
 17 19  1  0  0  0  0
 15 17  1  0  0  0  0
 15  7  1  0  0  0  0
  6  7  1  0  0  0  0
 20  6  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  1  0  0  0
 19 14  1  6  0  0  0
 20 13  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 24 23  1  1  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 24 20  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 30 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015119

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,17,21-25H,7-16H2,1H3/t21-,22+,23+,24-,25-,27-/m0/s1

> <INCHI_KEY>
UBWXUGDQUBIEIZ-QNTYDACNSA-N

> <FORMULA>
C27H34O3

> <MOLECULAR_WEIGHT>
406.5571

> <EXACT_MASS>
406.250794954

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.83030331681349

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
5.785410072666667

> <ALOGPS_LOGS>
-5.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.278885236855498

> <JCHEM_PKA_STRONGEST_BASIC>
-4.726056718914043

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
118.42909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.58e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015119
     RDKit          3D
Nandrolone phenpropionate
 64 68  0  0  0  0  0  0  0  0999 V2000
   -0.1715    0.7429    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169   -0.0775    0.0958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8053    0.7413   -1.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    1.3283   -0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1386    0.1942   -0.4315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4855    0.7146   -0.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9621    1.8271   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3765    2.2191   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1486    1.1693    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1901    1.4211    0.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7024   -0.2072   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4206   -0.4629   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -1.8088   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854   -1.9766    0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842   -0.7626    0.6559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3152   -1.2130    0.3259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6149   -1.9522    1.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -1.8807    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9057   -0.9005   -0.1660 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1221   -0.2056   -0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -0.4086   -1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -1.1704   -2.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147    0.2944   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1395   -0.3840   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    0.1124   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5321   -0.4815   -0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8355   -0.0077   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168    1.0507    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889    1.6344    0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7808    1.1612    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1008    1.8196    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    0.6115    2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7547    0.4411    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179    1.5809   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134    0.1156   -1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054    1.9556   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    1.9025    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658   -0.3851   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4953    1.0744    0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3256    2.7201   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7642    1.6226   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4801    3.1530   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9238    2.4477   -1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3773   -1.0532   -0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5472   -2.6069    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6304   -2.0196   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -2.2962    1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -2.8848    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661   -0.3325    1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017   -1.8381   -0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716   -1.3902    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -2.9908    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -2.8739    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -1.4771    1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418   -1.5057   -1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.1086   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    1.3682   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889   -0.1934    0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280   -1.4703   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3006   -1.3033   -1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6344   -0.4791   -1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1525    1.3802    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2915    2.4690    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    1.6182    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 16  2  1  0
 30 25  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  1
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  6
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  6
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  0
M  END

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0      -3.031   0.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.364  -0.386   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.031  -2.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.363  -2.696   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.970  -1.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.970   2.694   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.363   1.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.364  -1.926   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.698  -2.696   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.697  -0.386   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      -1.697   1.154   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      -1.697  -1.926   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.304   3.464   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.304  -1.156   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.363   0.384   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -0.363  -1.156   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       0.970  -0.386   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       0.970   1.154   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       2.304   0.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.304   1.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.769  -0.092   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.674   1.154   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.769   3.940   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.769   2.400   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.103   4.710   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.103   6.250   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.436   3.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.770   4.710   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.104   3.940   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.437   4.710   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.104   2.400   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.437   1.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.771   2.400   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.771   3.940   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    8                                                       
CONECT    3    8   12                                                       
CONECT    4   12    5                                                       
CONECT    5    4   17                                                       
CONECT    6    7   20                                                       
CONECT    7   15    6                                                       
CONECT    8    2    3    9                                                  
CONECT    9    8                                                            
CONECT   10    1   15   12   11                                             
CONECT   11   10                                                            
CONECT   12    3   10    4                                                  
CONECT   13   20                                                            
CONECT   14   19                                                            
CONECT   15   10   17    7   16                                             
CONECT   16   15                                                            
CONECT   17    5   19   15   18                                             
CONECT   18   17                                                            
CONECT   19   17   14   21   20                                             
CONECT   20    6   13   19   24                                             
CONECT   21   19   22                                                       
CONECT   22   21   24                                                       
CONECT   23   24   25                                                       
CONECT   24   23   22   20                                                  
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   34                                                       
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    HMDB0015119
HETATM    1  C1  UNL     1      -0.172   0.743   1.367  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.317  -0.077   0.096  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.805   0.741  -1.045  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.158   1.328  -0.616  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.139   0.194  -0.432  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.485   0.715  -0.059  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.962   1.827  -0.931  1.00  0.00           C  
HETATM    8  C8  UNL     1      -6.376   2.219  -0.670  1.00  0.00           C  
HETATM    9  C9  UNL     1      -7.149   1.169   0.046  1.00  0.00           C  
HETATM   10  O1  UNL     1      -8.190   1.421   0.721  1.00  0.00           O  
HETATM   11  C10 UNL     1      -6.702  -0.207  -0.024  1.00  0.00           C  
HETATM   12  C11 UNL     1      -5.421  -0.463  -0.076  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.832  -1.809  -0.154  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.585  -1.977   0.644  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.684  -0.763   0.656  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.315  -1.213   0.326  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.615  -1.952   1.432  1.00  0.00           C  
HETATM   18  C17 UNL     1       0.839  -1.881   1.035  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.906  -0.900  -0.166  1.00  0.00           C  
HETATM   20  O2  UNL     1       2.122  -0.206  -0.142  1.00  0.00           O  
HETATM   21  C19 UNL     1       2.983  -0.409  -1.211  1.00  0.00           C  
HETATM   22  O3  UNL     1       2.709  -1.170  -2.174  1.00  0.00           O  
HETATM   23  C20 UNL     1       4.315   0.294  -1.254  1.00  0.00           C  
HETATM   24  C21 UNL     1       5.139  -0.384  -0.179  1.00  0.00           C  
HETATM   25  C22 UNL     1       6.500   0.112  -0.039  1.00  0.00           C  
HETATM   26  C23 UNL     1       7.532  -0.482  -0.748  1.00  0.00           C  
HETATM   27  C24 UNL     1       8.835  -0.008  -0.597  1.00  0.00           C  
HETATM   28  C25 UNL     1       9.117   1.051   0.250  1.00  0.00           C  
HETATM   29  C26 UNL     1       8.089   1.634   0.948  1.00  0.00           C  
HETATM   30  C27 UNL     1       6.781   1.161   0.800  1.00  0.00           C  
HETATM   31  H1  UNL     1      -0.101   1.820   1.144  1.00  0.00           H  
HETATM   32  H2  UNL     1      -1.012   0.612   2.064  1.00  0.00           H  
HETATM   33  H3  UNL     1       0.755   0.441   1.938  1.00  0.00           H  
HETATM   34  H4  UNL     1      -0.118   1.581  -1.292  1.00  0.00           H  
HETATM   35  H5  UNL     1      -1.013   0.116  -1.912  1.00  0.00           H  
HETATM   36  H6  UNL     1      -2.505   1.956  -1.435  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.043   1.903   0.340  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.166  -0.385  -1.366  1.00  0.00           H  
HETATM   39  H9  UNL     1      -4.495   1.074   0.992  1.00  0.00           H  
HETATM   40  H10 UNL     1      -4.326   2.720  -0.701  1.00  0.00           H  
HETATM   41  H11 UNL     1      -4.764   1.623  -2.017  1.00  0.00           H  
HETATM   42  H12 UNL     1      -6.480   3.153  -0.073  1.00  0.00           H  
HETATM   43  H13 UNL     1      -6.924   2.448  -1.631  1.00  0.00           H  
HETATM   44  H14 UNL     1      -7.377  -1.053  -0.034  1.00  0.00           H  
HETATM   45  H15 UNL     1      -5.547  -2.607   0.164  1.00  0.00           H  
HETATM   46  H16 UNL     1      -4.630  -2.020  -1.244  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.868  -2.296   1.689  1.00  0.00           H  
HETATM   48  H18 UNL     1      -3.054  -2.885   0.235  1.00  0.00           H  
HETATM   49  H19 UNL     1      -2.766  -0.333   1.670  1.00  0.00           H  
HETATM   50  H20 UNL     1      -1.302  -1.838  -0.581  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.772  -1.390   2.374  1.00  0.00           H  
HETATM   52  H22 UNL     1      -0.981  -2.991   1.553  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.221  -2.874   0.700  1.00  0.00           H  
HETATM   54  H24 UNL     1       1.483  -1.477   1.820  1.00  0.00           H  
HETATM   55  H25 UNL     1       0.742  -1.506  -1.085  1.00  0.00           H  
HETATM   56  H26 UNL     1       4.813   0.109  -2.203  1.00  0.00           H  
HETATM   57  H27 UNL     1       4.202   1.368  -1.113  1.00  0.00           H  
HETATM   58  H28 UNL     1       4.589  -0.193   0.783  1.00  0.00           H  
HETATM   59  H29 UNL     1       5.128  -1.470  -0.381  1.00  0.00           H  
HETATM   60  H30 UNL     1       7.301  -1.303  -1.405  1.00  0.00           H  
HETATM   61  H31 UNL     1       9.634  -0.479  -1.156  1.00  0.00           H  
HETATM   62  H32 UNL     1      10.152   1.380   0.331  1.00  0.00           H  
HETATM   63  H33 UNL     1       8.291   2.469   1.622  1.00  0.00           H  
HETATM   64  H34 UNL     1       5.974   1.618   1.347  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   16   19
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   15   38
CONECT    6    7   12   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   10   11
CONECT   11   12   12   44
CONECT   12   13
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   49
CONECT   16   17   50
CONECT   17   18   51   52
CONECT   18   19   53   54
CONECT   19   20   55
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   56   57
CONECT   24   25   58   59
CONECT   25   26   26   30
CONECT   26   27   60
CONECT   27   28   28   61
CONECT   28   29   62
CONECT   29   30   30   63
CONECT   30   64
END

HMDB0015119
     RDKit          3D
Nandrolone phenpropionate
 64 68  0  0  0  0  0  0  0  0999 V2000
   -0.1715    0.7429    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169   -0.0775    0.0958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8053    0.7413   -1.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    1.3283   -0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1386    0.1942   -0.4315 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4855    0.7146   -0.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9621    1.8271   -0.9314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3765    2.2191   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1486    1.1693    0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1901    1.4211    0.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7024   -0.2072   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4206   -0.4629   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8319   -1.8088   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854   -1.9766    0.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842   -0.7626    0.6559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3152   -1.2130    0.3259 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6149   -1.9522    1.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -1.8807    1.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9057   -0.9005   -0.1660 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1221   -0.2056   -0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -0.4086   -1.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7094   -1.1704   -2.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147    0.2944   -1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1395   -0.3840   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5004    0.1124   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5321   -0.4815   -0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8355   -0.0077   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168    1.0507    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889    1.6344    0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7808    1.1612    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1008    1.8196    1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120    0.6115    2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7547    0.4411    1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179    1.5809   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0134    0.1156   -1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054    1.9556   -1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0434    1.9025    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1658   -0.3851   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4953    1.0744    0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3256    2.7201   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7642    1.6226   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4801    3.1530   -0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9238    2.4477   -1.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3773   -1.0532   -0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5472   -2.6069    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6304   -2.0196   -1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -2.2962    1.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -2.8848    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7661   -0.3325    1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3017   -1.8381   -0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7716   -1.3902    2.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -2.9908    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -2.8739    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -1.4771    1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418   -1.5057   -1.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8131    0.1086   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019    1.3682   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889   -0.1934    0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1280   -1.4703   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3006   -1.3033   -1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6344   -0.4791   -1.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1525    1.3802    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2915    2.4690    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9735    1.6182    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 16  2  1  0
 30 25  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  1
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  6
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  6
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 28 62  1  0
 29 63  1  0
 30 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
19NTPP	ChEBI
Durabolin	ChEBI
Nadrolone phenylpropionate	ChEBI
Nandrolon phenylpropionate	ChEBI
Nandrolone phenylpionate	ChEBI
Nandrolone phenylpropionate	ChEBI
Norandrolone phenyl propionate	ChEBI
Norandrostenolone phenylpropionate	ChEBI
Nortestosterone phenylpropionate	ChEBI
NPP	ChEBI
NTPP	ChEBI
Nadrolone phenylpropionic acid	Generator
Nandrolon phenylpropionic acid	Generator
Nandrolone phenylpionic acid	Generator
Nandrolone phenylpropionic acid	Generator
Norandrolone phenyl propionic acid	Generator
Norandrostenolone phenylpropionic acid	Generator
Nortestosterone phenylpropionic acid	Generator
Nandrolone phenpropionic acid	Generator
Nandrolin	HMDB
Testosterone phenylpropionate	HMDB
17 beta-Hydroxyestr-4-en-3-one hydrocinnamate	HMDB
Nandrolone phenpropionate, (17alpha)-isomer	HMDB
Fenobolin	HMDB
Nerobolyl	HMDB
Nerobolil	HMDB
Norandrolone phenylpropionate	HMDB

Chemical Formula

C₂₇H₃₄O₃

Average Molecular Weight

406.5571

Monoisotopic Molecular Weight

406.250794954

IUPAC Name

(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate

Traditional Name

(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate

CAS Registry Number

62-90-8

SMILES

[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C27H34O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,17,21-25H,7-16H2,1H3/t21-,22+,23+,24-,25-,27-/m0/s1

InChI Key

UBWXUGDQUBIEIZ-QNTYDACNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
Estrogen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Estrane-skeleton
Delta-4-steroid
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

3-phenylpropionate ester (CHEBI:7468 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00046 g/L	Not Available
LogP	2.62	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00046 g/L	ALOGPS
logP	4.22	ALOGPS
logP	5.79	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	19.28	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.43 m³·mol⁻¹	ChemAxon
Polarizability	47.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	197.583	31661259
DarkChem	[M-H]-	189.823	31661259
DeepCCS	[M-2H]-	233.893	30932474
DeepCCS	[M+Na]+	209.594	30932474
AllCCS	[M+H]+	205.7	32859911
AllCCS	[M+H-H2O]+	203.6	32859911
AllCCS	[M+NH4]+	207.6	32859911
AllCCS	[M+Na]+	208.1	32859911
AllCCS	[M-H]-	197.0	32859911
AllCCS	[M+Na-2H]-	197.8	32859911
AllCCS	[M+HCOO]-	198.7	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.	9.45 minutes	32390414
Predicted by Siyang on May 30, 2022	23.3439 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.34 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3528.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	657.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	291.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	289.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	624.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1024.9 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	973.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2022.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	680.1 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	2004.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	605.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	538.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	354.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	541.0 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nandrolone phenpropionate	[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	4424.8	Standard polar	33892256
Nandrolone phenpropionate	[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	3436.9	Standard non polar	33892256
Nandrolone phenpropionate	[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	3589.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nandrolone phenpropionate,1TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2OC(=O)CCC1=CC=CC=C1	3520.5	Semi standard non polar	33892256
Nandrolone phenpropionate,1TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2OC(=O)CCC1=CC=CC=C1	3392.6	Standard non polar	33892256
Nandrolone phenpropionate,1TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2OC(=O)CCC1=CC=CC=C1	4113.0	Standard polar	33892256
Nandrolone phenpropionate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC(=O)CCC3=CC=CC=C3)CC[C@@H]12	3798.8	Semi standard non polar	33892256
Nandrolone phenpropionate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC(=O)CCC3=CC=CC=C3)CC[C@@H]12	3630.9	Standard non polar	33892256
Nandrolone phenpropionate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC(=O)CCC3=CC=CC=C3)CC[C@@H]12	4237.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nandrolone phenpropionate GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-2794000000-8a406f2131925f7d78d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nandrolone phenpropionate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nandrolone phenpropionate 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 - Nandrolone phenpropionate 10V, Positive-QTOF	splash10-0a4i-2693800000-014d5a8f5785d5fa2138	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Positive-QTOF	splash10-0a59-2891000000-0d191fd67047632bac0b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Positive-QTOF	splash10-002f-2290000000-d1eb49bea81bc4fe8fec	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 10V, Negative-QTOF	splash10-0a4i-0250900000-73ea898c756aee0d065d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Negative-QTOF	splash10-05fr-0491200000-c48f4cd0cb4d262db924	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Negative-QTOF	splash10-006x-2290000000-2d0ca51aad14a4610e02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 10V, Positive-QTOF	splash10-0a4i-2290300000-bac5d57e78f5058c299b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Positive-QTOF	splash10-0a4l-5931100000-59cd27d9e64a7d2840f5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Positive-QTOF	splash10-0a4u-3920000000-ff8ab93696f1c30ae190	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 10V, Negative-QTOF	splash10-0a4i-0000900000-c12aa2fec47362dfe817	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 20V, Negative-QTOF	splash10-0a4i-2311900000-d39466b8e277a338d135	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nandrolone phenpropionate 40V, Negative-QTOF	splash10-004i-9707100000-32c75e3ec9135a8c9585	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00984	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00984	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00984

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

199761

KEGG Compound ID

C08155

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nandrolone phenylpropionate

METLIN ID

Not Available

PubChem Compound

229455

PDB ID

Not Available

ChEBI ID

7468

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)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
InChem Data Sheet [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

References

Cen Y, Li K, Liu XX: [Effect of nandrolone phenylpropionate on expression of hepatic albumin-mRNA and androgen receptor in burned rats]. Zhongguo Xiu Fu Chong Jian Wai Ke Za Zhi. 2003 Nov;17(6):439-41. [PubMed:14663936 ]
Li K, Cen Y, Liu X, Luo X: [The effects of nandrolone phenylpropionate on androgen receptor of liver and sexual glands in burned rats]. Sichuan Da Xue Xue Bao Yi Xue Ban. 2003 Oct;34(4):708-10. [PubMed:14619588 ]
Burger LL, Haisenleder DJ, Wotton GM, Aylor KW, Dalkin AC, Marshall JC: The regulation of FSHbeta transcription by gonadal steroids: testosterone and estradiol modulation of the activin intracellular signaling pathway. Am J Physiol Endocrinol Metab. 2007 Jul;293(1):E277-85. Epub 2007 Apr 3. [PubMed:17405825 ]
Fujii Y, Kawakami S, Okada Y, Kageyama Y, Kihara K: Regulation of prostate-specific antigen by activin A in prostate cancer LNCaP cells. Am J Physiol Endocrinol Metab. 2004 Jun;286(6):E927-31. Epub 2004 Feb 3. [PubMed:14761877 ]
Yan W, Burns KH, Matzuk MM: Genetic engineering to study testicular tumorigenesis. APMIS. 2003 Jan;111(1):174-81; discussion 182-3. [PubMed:12760377 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Nandrolone phenpropionate (HMDB0015119)

MOL for HMDB0015119 (Nandrolone phenpropionate)

3D MOL for HMDB0015119 (Nandrolone phenpropionate)

3D SDF for HMDB0015119 (Nandrolone phenpropionate)

3D-SDF for HMDB0015119 (Nandrolone phenpropionate)

PDB for HMDB0015119 (Nandrolone phenpropionate)

3D PDB for HMDB0015119 (Nandrolone phenpropionate)

SMILES for HMDB0015119 (Nandrolone phenpropionate)

INCHI for HMDB0015119 (Nandrolone phenpropionate)

Structure for HMDB0015119 (Nandrolone phenpropionate)

3D Structure for HMDB0015119 (Nandrolone phenpropionate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References