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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 20:26:51 UTC

Update Date

2021-09-24 20:26:52 UTC

HMDB ID

HMDB0304871

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lonafarnib

Description

Lonafarnib, also known as zokinvy or SCH 66336, belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle. Based on a literature review a significant number of articles have been published on Lonafarnib.

Structure

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


  Mrv0541 02231218162D          

 36 40  0  0  1  0            999 V2000
    3.6447    2.0263    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.9819    4.1595    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.1595    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1015   -0.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -4.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    0.5896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -3.1229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801    2.8285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449   -4.3605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    3.0647    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5304    1.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1015    1.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304    1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1015    1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -1.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0727    3.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5593    3.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428    4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2285    4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518    2.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719    4.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    4.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287    3.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374    3.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -3.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0032    3.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1945    3.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 36  1  0  0  0  0
  3 33  1  0  0  0  0
  4 20  2  0  0  0  0
  5 34  2  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 20  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 34  1  0  0  0  0
  8 18  1  0  0  0  0
  8 35  2  0  0  0  0
  9 34  1  0  0  0  0
 11 10  1  6  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 19  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  2  0  0  0  0
 17 29  1  0  0  0  0
 18 24  2  0  0  0  0
 19 20  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 23 30  1  0  0  0  0
 24 28  1  0  0  0  0
 24 31  1  0  0  0  0
 27 28  1  0  0  0  0
 29 32  2  0  0  0  0
 30 33  2  0  0  0  0
 31 36  2  0  0  0  0
 32 33  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

HMDB0304871
     RDKit          3D
Lonafarnib
 67 71  0  0  0  0  0  0  0  0999 V2000
    8.6975   -1.3597    0.7597 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0393   -0.7026   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5877   -0.6396   -1.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7644   -0.1132   -0.1320 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -0.1581    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031   -0.7465    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759   -0.3075   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    1.0039   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105    0.9939    0.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059    1.1793    2.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428    0.7957    0.7502 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    0.5786   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578    1.2421   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    0.5636    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4754   -0.3994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8355   -1.1269    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804   -2.4306    0.7310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3315   -3.2189    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4063   -2.7032    2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4717   -3.8422    3.3436 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6976   -1.3685    2.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -0.5629    1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    0.8365    1.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5344    1.3982   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    0.9105   -1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4229    1.3876   -2.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9674    1.0885   -3.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7809    1.6921   -5.0947 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.3037   -3.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -0.1901   -2.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -1.3174   -3.0029 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786    0.1338   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273   -0.0093    1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993    0.8026    1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8046   -0.2425   -1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    0.5547   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0783   -2.3307    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8152   -0.9324    1.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0827    0.8376    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6505   -0.8383    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1034   -0.5805    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8559   -1.8580    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -1.0811   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273    1.2662   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810    1.8328    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760    1.0340   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -0.5150   -0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3659    1.3539   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    2.2807   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7498    1.3886    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876   -1.2637   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048   -4.2693    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.9227    2.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3476    0.8935    1.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786    1.4148    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6364    1.4212   -0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2869    2.5143   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3034    2.0100   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717    0.0479   -4.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -1.0680    1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0209    0.0452    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104    1.8554    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099    0.3854    2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    0.2773   -2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -1.2614   -1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6436    0.5219   -2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8379    1.5904   -0.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 14 33  1  0
 33 34  1  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34 11  1  0
 32 15  1  0
 22 16  1  0
 32 25  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  6
 18 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 26 58  1  0
 29 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 34 63  1  0
 35 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  1  0
M  END


  Mrv0541 02231218162D          

 36 40  0  0  1  0            999 V2000
    3.6447    2.0263    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.9819    4.1595    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    4.1595    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1015   -0.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -4.3605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    0.5896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -3.1229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801    2.8285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449   -4.3605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    2.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159    3.0647    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5304    1.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1015    1.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304    1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1015    1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -1.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0727    3.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5593    3.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449   -1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428    4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2449   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2285    4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4518    2.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719    4.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    4.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6287    3.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374    3.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -3.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0032    3.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1945    3.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0  0  0  0
  2 36  1  0  0  0  0
  3 33  1  0  0  0  0
  4 20  2  0  0  0  0
  5 34  2  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 20  1  0  0  0  0
  7 25  1  0  0  0  0
  7 26  1  0  0  0  0
  7 34  1  0  0  0  0
  8 18  1  0  0  0  0
  8 35  2  0  0  0  0
  9 34  1  0  0  0  0
 11 10  1  6  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 19  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  2  0  0  0  0
 17 29  1  0  0  0  0
 18 24  2  0  0  0  0
 19 20  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 23 30  1  0  0  0  0
 24 28  1  0  0  0  0
 24 31  1  0  0  0  0
 27 28  1  0  0  0  0
 29 32  2  0  0  0  0
 30 33  2  0  0  0  0
 31 36  2  0  0  0  0
 32 33  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304871

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)N1CCC(CC(=O)N2CCC(CC2)[C@H]2C3=C(CCC4=C2C(Br)=CC(Cl)=C4)C=C(Br)C=N3)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1

> <INCHI_KEY>
DHMTURDWPRKSOA-RUZDIDTESA-N

> <FORMULA>
C27H31Br2ClN4O2

> <MOLECULAR_WEIGHT>
638.822

> <EXACT_MASS>
636.050229257

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
60.094736593824436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-{4-[(2R)-6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide

> <ALOGPS_LOGP>
5.34

> <JCHEM_LOGP>
4.739098369666667

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.745956271178471

> <JCHEM_PKA_STRONGEST_BASIC>
3.2822339239325258

> <JCHEM_POLAR_SURFACE_AREA>
79.53

> <JCHEM_REFRACTIVITY>
149.31459999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lonafarnib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304871
     RDKit          3D
Lonafarnib
 67 71  0  0  0  0  0  0  0  0999 V2000
    8.6975   -1.3597    0.7597 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0393   -0.7026   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5877   -0.6396   -1.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7644   -0.1132   -0.1320 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -0.1581    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031   -0.7465    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759   -0.3075   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    1.0039   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105    0.9939    0.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059    1.1793    2.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428    0.7957    0.7502 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    0.5786   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578    1.2421   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    0.5636    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4754   -0.3994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8355   -1.1269    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804   -2.4306    0.7310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3315   -3.2189    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4063   -2.7032    2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4717   -3.8422    3.3436 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6976   -1.3685    2.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -0.5629    1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    0.8365    1.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5344    1.3982   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    0.9105   -1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4229    1.3876   -2.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9674    1.0885   -3.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7809    1.6921   -5.0947 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.3037   -3.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -0.1901   -2.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -1.3174   -3.0029 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786    0.1338   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273   -0.0093    1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993    0.8026    1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8046   -0.2425   -1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    0.5547   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0783   -2.3307    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8152   -0.9324    1.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0827    0.8376    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6505   -0.8383    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1034   -0.5805    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8559   -1.8580    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -1.0811   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273    1.2662   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810    1.8328    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760    1.0340   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -0.5150   -0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3659    1.3539   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    2.2807   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7498    1.3886    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876   -1.2637   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048   -4.2693    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.9227    2.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3476    0.8935    1.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786    1.4148    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6364    1.4212   -0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2869    2.5143   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3034    2.0100   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717    0.0479   -4.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -1.0680    1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0209    0.0452    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104    1.8554    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099    0.3854    2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    0.2773   -2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -1.2614   -1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6436    0.5219   -2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8379    1.5904   -0.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 14 33  1  0
 33 34  1  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34 11  1  0
 32 15  1  0
 22 16  1  0
 32 25  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  6
 18 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 26 58  1  0
 29 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 34 63  1  0
 35 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  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 Br   UNK     0       6.803   3.782   0.000  0.00  0.00          Br+0
HETATM    2 Br   UNK     0      14.900   7.764   0.000  0.00  0.00          Br+0
HETATM    3 Cl   UNK     0       3.080   7.764   0.000  0.00  0.00          Cl+0
HETATM    4  O   UNK     0       7.656  -1.209   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.990  -8.140   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.990   1.101   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.323  -5.829   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      11.536   5.280   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      11.657  -8.140   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.990   4.181   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.990   5.721   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.323   3.411   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.656   3.411   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.323   1.871   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.656   1.871   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.323  -2.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.602   6.389   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.377   6.389   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.323  -1.209   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.990  -0.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.990  -3.519   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.657  -3.519   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.259   7.890   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.720   7.890   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.990  -5.059   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.657  -5.059   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.220   9.094   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.760   9.094   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.443   5.280   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.734   8.387   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.245   8.387   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.907   5.741   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.550   7.305   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.323  -7.369   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.073   5.741   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.430   7.305   0.000  0.00  0.00           C+0
CONECT    1   29                                                            
CONECT    2   36                                                            
CONECT    3   33                                                            
CONECT    4   20                                                            
CONECT    5   34                                                            
CONECT    6   14   15   20                                                  
CONECT    7   25   26   34                                                  
CONECT    8   18   35                                                       
CONECT    9   34                                                            
CONECT   10   11   12   13                                                  
CONECT   11   10   17   18                                                  
CONECT   12   10   14                                                       
CONECT   13   10   15                                                       
CONECT   14    6   12                                                       
CONECT   15    6   13                                                       
CONECT   16   19   21   22                                                  
CONECT   17   11   23   29                                                  
CONECT   18    8   11   24                                                  
CONECT   19   16   20                                                       
CONECT   20    4    6   19                                                  
CONECT   21   16   25                                                       
CONECT   22   16   26                                                       
CONECT   23   17   27   30                                                  
CONECT   24   18   28   31                                                  
CONECT   25    7   21                                                       
CONECT   26    7   22                                                       
CONECT   27   23   28                                                       
CONECT   28   24   27                                                       
CONECT   29    1   17   32                                                  
CONECT   30   23   33                                                       
CONECT   31   24   36                                                       
CONECT   32   29   33                                                       
CONECT   33    3   30   32                                                  
CONECT   34    5    7    9                                                  
CONECT   35    8   36                                                       
CONECT   36    2   31   35                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0304871
HETATM    1  N1  UNL     1       8.697  -1.360   0.760  1.00  0.00           N  
HETATM    2  C1  UNL     1       8.039  -0.703  -0.311  1.00  0.00           C  
HETATM    3  O1  UNL     1       8.588  -0.640  -1.433  1.00  0.00           O  
HETATM    4  N2  UNL     1       6.764  -0.113  -0.132  1.00  0.00           N  
HETATM    5  C2  UNL     1       6.092  -0.158   1.140  1.00  0.00           C  
HETATM    6  C3  UNL     1       4.703  -0.747   1.004  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.976  -0.308  -0.219  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.237   1.004  -0.069  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.211   0.994   0.977  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.606   1.179   2.167  1.00  0.00           O  
HETATM   11  N3  UNL     1       0.843   0.796   0.750  1.00  0.00           N  
HETATM   12  C7  UNL     1       0.312   0.579  -0.562  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.058   1.242  -0.592  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.046   0.564   0.318  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.858  -0.475  -0.399  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.835  -1.127   0.567  1.00  0.00           C  
HETATM   17  N4  UNL     1      -3.580  -2.431   0.731  1.00  0.00           N  
HETATM   18  C12 UNL     1      -4.332  -3.219   1.527  1.00  0.00           C  
HETATM   19  C13 UNL     1      -5.406  -2.703   2.212  1.00  0.00           C  
HETATM   20 BR1  UNL     1      -6.472  -3.842   3.344  1.00  0.00          BR  
HETATM   21  C14 UNL     1      -5.698  -1.369   2.068  1.00  0.00           C  
HETATM   22  C15 UNL     1      -4.897  -0.563   1.229  1.00  0.00           C  
HETATM   23  C16 UNL     1      -5.351   0.836   1.225  1.00  0.00           C  
HETATM   24  C17 UNL     1      -5.534   1.398  -0.106  1.00  0.00           C  
HETATM   25  C18 UNL     1      -4.781   0.911  -1.248  1.00  0.00           C  
HETATM   26  C19 UNL     1      -5.423   1.388  -2.406  1.00  0.00           C  
HETATM   27  C20 UNL     1      -4.967   1.088  -3.659  1.00  0.00           C  
HETATM   28 CL1  UNL     1      -5.781   1.692  -5.095  1.00  0.00          CL  
HETATM   29  C21 UNL     1      -3.857   0.304  -3.844  1.00  0.00           C  
HETATM   30  C22 UNL     1      -3.191  -0.190  -2.719  1.00  0.00           C  
HETATM   31 BR2  UNL     1      -1.677  -1.317  -3.003  1.00  0.00          BR  
HETATM   32  C23 UNL     1      -3.679   0.134  -1.487  1.00  0.00           C  
HETATM   33  C24 UNL     1      -1.327  -0.009   1.521  1.00  0.00           C  
HETATM   34  C25 UNL     1      -0.099   0.803   1.852  1.00  0.00           C  
HETATM   35  C26 UNL     1       4.805  -0.242  -1.456  1.00  0.00           C  
HETATM   36  C27 UNL     1       6.091   0.555  -1.229  1.00  0.00           C  
HETATM   37  H1  UNL     1       9.078  -2.331   0.551  1.00  0.00           H  
HETATM   38  H2  UNL     1       8.815  -0.932   1.715  1.00  0.00           H  
HETATM   39  H3  UNL     1       6.083   0.838   1.599  1.00  0.00           H  
HETATM   40  H4  UNL     1       6.651  -0.838   1.823  1.00  0.00           H  
HETATM   41  H5  UNL     1       4.103  -0.580   1.897  1.00  0.00           H  
HETATM   42  H6  UNL     1       4.856  -1.858   0.915  1.00  0.00           H  
HETATM   43  H7  UNL     1       3.174  -1.081  -0.411  1.00  0.00           H  
HETATM   44  H8  UNL     1       2.827   1.266  -1.063  1.00  0.00           H  
HETATM   45  H9  UNL     1       3.981   1.833   0.142  1.00  0.00           H  
HETATM   46  H10 UNL     1       0.876   1.034  -1.387  1.00  0.00           H  
HETATM   47  H11 UNL     1       0.256  -0.515  -0.760  1.00  0.00           H  
HETATM   48  H12 UNL     1      -1.366   1.354  -1.625  1.00  0.00           H  
HETATM   49  H13 UNL     1      -0.874   2.281  -0.205  1.00  0.00           H  
HETATM   50  H14 UNL     1      -2.750   1.389   0.636  1.00  0.00           H  
HETATM   51  H15 UNL     1      -2.188  -1.264  -0.763  1.00  0.00           H  
HETATM   52  H16 UNL     1      -4.105  -4.269   1.644  1.00  0.00           H  
HETATM   53  H17 UNL     1      -6.533  -0.923   2.588  1.00  0.00           H  
HETATM   54  H18 UNL     1      -6.348   0.894   1.764  1.00  0.00           H  
HETATM   55  H19 UNL     1      -4.679   1.415   1.907  1.00  0.00           H  
HETATM   56  H20 UNL     1      -6.636   1.421  -0.342  1.00  0.00           H  
HETATM   57  H21 UNL     1      -5.287   2.514  -0.033  1.00  0.00           H  
HETATM   58  H22 UNL     1      -6.303   2.010  -2.335  1.00  0.00           H  
HETATM   59  H23 UNL     1      -3.472   0.048  -4.831  1.00  0.00           H  
HETATM   60  H24 UNL     1      -1.060  -1.068   1.384  1.00  0.00           H  
HETATM   61  H25 UNL     1      -2.021   0.045   2.385  1.00  0.00           H  
HETATM   62  H26 UNL     1      -0.410   1.855   2.063  1.00  0.00           H  
HETATM   63  H27 UNL     1       0.410   0.385   2.729  1.00  0.00           H  
HETATM   64  H28 UNL     1       4.233   0.277  -2.233  1.00  0.00           H  
HETATM   65  H29 UNL     1       5.092  -1.261  -1.764  1.00  0.00           H  
HETATM   66  H30 UNL     1       6.644   0.522  -2.167  1.00  0.00           H  
HETATM   67  H31 UNL     1       5.838   1.590  -0.895  1.00  0.00           H  
CONECT    1    2   37   38
CONECT    2    3    3    4
CONECT    4    5   36
CONECT    5    6   39   40
CONECT    6    7   41   42
CONECT    7    8   35   43
CONECT    8    9   44   45
CONECT    9   10   10   11
CONECT   11   12   34
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   33   50
CONECT   15   16   32   51
CONECT   16   17   17   22
CONECT   17   18
CONECT   18   19   19   52
CONECT   19   20   21
CONECT   21   22   22   53
CONECT   22   23
CONECT   23   24   54   55
CONECT   24   25   56   57
CONECT   25   26   26   32
CONECT   26   27   58
CONECT   27   28   29   29
CONECT   29   30   59
CONECT   30   31   32   32
CONECT   33   34   60   61
CONECT   34   62   63
CONECT   35   36   64   65
CONECT   36   66   67
END

HMDB0304871
     RDKit          3D
Lonafarnib
 67 71  0  0  0  0  0  0  0  0999 V2000
    8.6975   -1.3597    0.7597 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0393   -0.7026   -0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5877   -0.6396   -1.4327 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7644   -0.1132   -0.1320 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0923   -0.1581    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031   -0.7465    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759   -0.3075   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    1.0039   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2105    0.9939    0.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059    1.1793    2.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428    0.7957    0.7502 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    0.5786   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578    1.2421   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    0.5636    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578   -0.4754   -0.3994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8355   -1.1269    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5804   -2.4306    0.7310 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3315   -3.2189    1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4063   -2.7032    2.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4717   -3.8422    3.3436 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.6976   -1.3685    2.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8966   -0.5629    1.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3514    0.8365    1.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5344    1.3982   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7813    0.9105   -1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4229    1.3876   -2.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9674    1.0885   -3.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7809    1.6921   -5.0947 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    0.3037   -3.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914   -0.1901   -2.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771   -1.3174   -3.0029 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6786    0.1338   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273   -0.0093    1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0993    0.8026    1.8517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8046   -0.2425   -1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0911    0.5547   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0783   -2.3307    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8152   -0.9324    1.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0827    0.8376    1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6505   -0.8383    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1034   -0.5805    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8559   -1.8580    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738   -1.0811   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273    1.2662   -1.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810    1.8328    0.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760    1.0340   -1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -0.5150   -0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3659    1.3539   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    2.2807   -0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7498    1.3886    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876   -1.2637   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048   -4.2693    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.9227    2.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3476    0.8935    1.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6786    1.4148    1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6364    1.4212   -0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2869    2.5143   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3034    2.0100   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717    0.0479   -4.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596   -1.0680    1.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0209    0.0452    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4104    1.8554    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099    0.3854    2.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330    0.2773   -2.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -1.2614   -1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6436    0.5219   -2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8379    1.5904   -0.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 14 33  1  0
 33 34  1  0
  7 35  1  0
 35 36  1  0
 36  4  1  0
 34 11  1  0
 32 15  1  0
 22 16  1  0
 32 25  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  6
 18 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 26 58  1  0
 29 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 34 63  1  0
 35 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lonafarnibum	ChEBI
SCH 66336	ChEBI
Zokinvy	Kegg
(+)4-(2-(4-(8-Chloro-3,10-dibromo-6,11-dihydro-5H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-yl)-1-piperidinyl)-2-oxoethyl)-1-piperidinecarboxamide	MeSH
4-(2-(4-(8-Chloro-3,10-dibromo-6,11-dihydro-5H-benzo-(5,6)-cyclohepta(1,2-b)-pyridin-11(R)-yl)-1-piperidinyl)-2-oxo-ethyl)-1-piperidinecarboxamide	MeSH

Chemical Formula

C₂₇H₃₁Br₂ClN₄O₂

Average Molecular Weight

638.822

Monoisotopic Molecular Weight

636.050229257

IUPAC Name

4-(2-{4-[(2R)-6,15-dibromo-13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide

Traditional Name

lonafarnib

CAS Registry Number

Not Available

SMILES

NC(=O)N1CCC(CC(=O)N2CCC(CC2)[C@H]2C3=C(CCC4=C2C(Br)=CC(Cl)=C4)C=C(Br)C=N3)CC1

InChI Identifier

InChI=1S/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1

InChI Key

DHMTURDWPRKSOA-RUZDIDTESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzocycloheptapyridines

Sub Class

Not Available

Direct Parent

Benzocycloheptapyridines

Alternative Parents

Substituents

Benzocycloheptapyridine
N-acyl-piperidine
Piperidinecarboxamide
1-piperidinecarboxamide
Aryl bromide
Aryl chloride
Aryl halide
Benzenoid
Pyridine
Piperidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Carboxamide group
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organobromide
Organohalogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.34	ALOGPS
logP	4.74	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	15.75	ChemAxon
pKa (Strongest Basic)	3.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	79.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	149.31 m³·mol⁻¹	ChemAxon
Polarizability	60.09 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
AllCCS	[M+H]+	222.29	32859911
AllCCS	[M+H-H2O]+	221.392	32859911
AllCCS	[M+Na]+	223.303	32859911
AllCCS	[M+NH4]+	223.082	32859911
AllCCS	[M-H]-	223.643	32859911
AllCCS	[M+Na-2H]-	226.007	32859911
AllCCS	[M+HCOO]-	228.729	32859911
DeepCCS	[M+H]+	217.338	30932474
DeepCCS	[M-H]-	214.942	30932474
DeepCCS	[M-2H]-	247.826	30932474
DeepCCS	[M+Na]+	223.25	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lonafarnib,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1	4884.0	Semi standard non polar	33892256
Lonafarnib,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1	4332.9	Standard non polar	33892256
Lonafarnib,1TMS,isomer #1	C[Si](C)(C)NC(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1	6147.2	Standard polar	33892256
Lonafarnib,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1)[Si](C)(C)C	4805.1	Semi standard non polar	33892256
Lonafarnib,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1)[Si](C)(C)C	4438.8	Standard non polar	33892256
Lonafarnib,2TMS,isomer #1	C[Si](C)(C)N(C(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1)[Si](C)(C)C	5792.6	Standard polar	33892256
Lonafarnib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1	5089.2	Semi standard non polar	33892256
Lonafarnib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1	4571.0	Standard non polar	33892256
Lonafarnib,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1	6115.6	Standard polar	33892256
Lonafarnib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1)[Si](C)(C)C(C)(C)C	5143.0	Semi standard non polar	33892256
Lonafarnib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1)[Si](C)(C)C(C)(C)C	4858.1	Standard non polar	33892256
Lonafarnib,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)N1CCC(CC(=O)N2CCC([C@H]3C4=NC=C(Br)C=C4CCC4=CC(Cl)=CC(Br)=C43)CC2)CC1)[Si](C)(C)C(C)(C)C	5711.7	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 10V, Positive-QTOF	splash10-000i-0100329000-643455dda7deee94681b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 20V, Positive-QTOF	splash10-00kg-7801964000-b8988312dd2234aec574	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 40V, Positive-QTOF	splash10-000t-9301500000-605e3ba5bcb521beed99	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 10V, Negative-QTOF	splash10-0006-9000085000-354132d85002e9f3cd05	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 20V, Negative-QTOF	splash10-0006-5200491000-5648f0764c872fad33e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 40V, Negative-QTOF	splash10-0006-9001310000-569fe2ff576a7513c195	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 10V, Positive-QTOF	splash10-000i-0000009000-f09c9acab9bc87a6e2b7	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 20V, Positive-QTOF	splash10-0079-0000269000-c61f946ade777d02ea71	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 40V, Positive-QTOF	splash10-0uyl-2011691000-053b9a4e13a332e03e7f	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 10V, Negative-QTOF	splash10-000i-0000009000-cfc491868e19992aa76a	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 20V, Negative-QTOF	splash10-000l-6100097000-3c5156f70c69dd47cc05	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lonafarnib 40V, Negative-QTOF	splash10-002f-9210241000-0637f41214476473c72e	2021-10-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06448

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

130645

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lonafarnib

METLIN ID

Not Available

PubChem Compound

148195

PDB ID

Not Available

ChEBI ID

47097

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

Not Available

Showing metabocard for Lonafarnib (HMDB0304871)

MOL for HMDB0304871 (Lonafarnib)

3D MOL for HMDB0304871 (Lonafarnib)

3D SDF for HMDB0304871 (Lonafarnib)

3D-SDF for HMDB0304871 (Lonafarnib)

PDB for HMDB0304871 (Lonafarnib)

3D PDB for HMDB0304871 (Lonafarnib)

SMILES for HMDB0304871 (Lonafarnib)

INCHI for HMDB0304871 (Lonafarnib)

Structure for HMDB0304871 (Lonafarnib)

3D Structure for HMDB0304871 (Lonafarnib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra