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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:37:17 UTC

Update Date

2021-09-26 23:17:31 UTC

HMDB ID

HMDB0259764

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vanoxerine

Description

Vanoxerine, also known as GBR 12909, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. Based on a literature review a significant number of articles have been published on Vanoxerine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vanoxerine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vanoxerine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1533004261514462D          

 33 36  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  END

HMDB0259764
     RDKit          3D
Vanoxerine
 65 68  0  0  0  0  0  0  0  0999 V2000
   -5.6191   -4.6646   -2.7209 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422   -3.5957   -1.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1840   -3.7936   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8133   -2.7395    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030   -1.4946   -0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1111   -0.3780    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    0.3061   -0.0226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835    0.2384    0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881    1.0240    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879    0.6211   -0.7527 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7797    1.6326   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    1.7659   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.5408    0.0966 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9663    0.7114   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7267    1.6504    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1239    1.8107    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7795    0.4971   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906    0.0435    1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1091   -1.1936    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0121   -1.9750   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2891   -1.4946   -1.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6758   -0.2712   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9889   -0.5804   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -0.6199   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724    0.5271    0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9301    0.4524    1.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0125    1.2350    2.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4699    2.1461    1.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5470    2.9454    1.6287 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8323    2.2458    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    1.4380   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5712   -1.3289   -1.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9436   -2.3840   -2.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4084   -4.7193   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7430   -2.8156    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8135   -0.7685    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.8242    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3386    0.6805    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164    0.8431    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    2.1041    0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252    1.4927   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    2.6050   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720    2.1017    0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612    2.5444   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310    1.0348   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -0.3185   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214    1.1249    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084    2.5869    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146    2.5367    0.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0710    2.2664   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5771    0.6541    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6714   -1.5186    1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5058   -2.9563   -0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2337   -2.1448   -2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1221    0.0470   -2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097   -0.6167   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -1.4977   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321   -1.2141    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352   -1.2467   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020   -0.2579    2.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5269    1.1683    3.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2131    2.9578   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437    1.5164   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3362   -0.3805   -2.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0134   -2.3037   -3.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13 23  1  0
 23 24  1  0
  6 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
  5 32  1  0
 32 33  2  0
 33  2  1  0
 24 10  1  0
 31 25  1  0
 22 17  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  0
 33 65  1  0
M  END


  Mrv1533004261514462D          

 33 36  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259764

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC=C(C=C1)C(OCCN1CCN(CCCC2=CC=CC=C2)CC1)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32F2N2O/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23/h1-3,5-6,8-15,28H,4,7,16-22H2

> <INCHI_KEY>
NAUWTFJOPJWYOT-UHFFFAOYSA-N

> <FORMULA>
C28H32F2N2O

> <MOLECULAR_WEIGHT>
450.574

> <EXACT_MASS>
450.248269984

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.92944485795749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine

> <ALOGPS_LOGP>
4.90

> <JCHEM_LOGP>
6.242133701

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.577007711216265

> <JCHEM_POLAR_SURFACE_AREA>
15.71

> <JCHEM_REFRACTIVITY>
130.3785

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vanoxerine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0259764
     RDKit          3D
Vanoxerine
 65 68  0  0  0  0  0  0  0  0999 V2000
   -5.6191   -4.6646   -2.7209 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422   -3.5957   -1.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1840   -3.7936   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8133   -2.7395    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030   -1.4946   -0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1111   -0.3780    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    0.3061   -0.0226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835    0.2384    0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881    1.0240    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879    0.6211   -0.7527 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7797    1.6326   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    1.7659   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.5408    0.0966 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9663    0.7114   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7267    1.6504    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1239    1.8107    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7795    0.4971   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906    0.0435    1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1091   -1.1936    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0121   -1.9750   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2891   -1.4946   -1.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6758   -0.2712   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9889   -0.5804   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -0.6199   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724    0.5271    0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9301    0.4524    1.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0125    1.2350    2.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4699    2.1461    1.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5470    2.9454    1.6287 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8323    2.2458    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    1.4380   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5712   -1.3289   -1.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9436   -2.3840   -2.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4084   -4.7193   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7430   -2.8156    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8135   -0.7685    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.8242    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3386    0.6805    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164    0.8431    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    2.1041    0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252    1.4927   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    2.6050   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720    2.1017    0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612    2.5444   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310    1.0348   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -0.3185   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214    1.1249    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084    2.5869    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146    2.5367    0.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0710    2.2664   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5771    0.6541    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6714   -1.5186    1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5058   -2.9563   -0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2337   -2.1448   -2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1221    0.0470   -2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097   -0.6167   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -1.4977   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321   -1.2141    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352   -1.2467   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020   -0.2579    2.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5269    1.1683    3.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2131    2.9578   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437    1.5164   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3362   -0.3805   -2.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0134   -2.3037   -3.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13 23  1  0
 23 24  1  0
  6 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
  5 32  1  0
 32 33  2  0
 33  2  1  0
 24 10  1  0
 31 25  1  0
 22 17  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  0
 33 65  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -5.335  -0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   26  F   UNK     0      -2.667 -13.860   0.000  0.00  0.00           F+0
HETATM   27  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   33  F   UNK     0       2.667  -4.620   0.000  0.00  0.00           F+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    3   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   23                                                            
CONECT   27   19   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    HMDB0259764
HETATM    1  F1  UNL     1      -5.619  -4.665  -2.721  1.00  0.00           F  
HETATM    2  C1  UNL     1      -5.242  -3.596  -1.951  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.184  -3.794  -0.601  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.813  -2.740   0.199  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.503  -1.495  -0.363  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.111  -0.378   0.513  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.024   0.306  -0.023  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.983   0.238   0.899  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.788   1.024   0.474  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.188   0.621  -0.753  1.00  0.00           N  
HETATM   11  C8  UNL     1       0.780   1.633  -1.129  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.848   1.766  -0.103  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.585   0.541   0.097  1.00  0.00           N  
HETATM   14  C10 UNL     1       3.966   0.711  -0.342  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.727   1.650   0.554  1.00  0.00           C  
HETATM   16  C12 UNL     1       6.124   1.811   0.012  1.00  0.00           C  
HETATM   17  C13 UNL     1       6.780   0.497  -0.039  1.00  0.00           C  
HETATM   18  C14 UNL     1       7.491   0.043   1.033  1.00  0.00           C  
HETATM   19  C15 UNL     1       8.109  -1.194   0.982  1.00  0.00           C  
HETATM   20  C16 UNL     1       8.012  -1.975  -0.149  1.00  0.00           C  
HETATM   21  C17 UNL     1       7.289  -1.495  -1.216  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.676  -0.271  -1.169  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.989  -0.580  -0.565  1.00  0.00           C  
HETATM   24  C20 UNL     1       0.519  -0.620  -0.635  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.272   0.527   0.730  1.00  0.00           C  
HETATM   26  C22 UNL     1      -5.930   0.452   1.935  1.00  0.00           C  
HETATM   27  C23 UNL     1      -7.012   1.235   2.259  1.00  0.00           C  
HETATM   28  C24 UNL     1      -7.470   2.146   1.334  1.00  0.00           C  
HETATM   29  F2  UNL     1      -8.547   2.945   1.629  1.00  0.00           F  
HETATM   30  C25 UNL     1      -6.832   2.246   0.115  1.00  0.00           C  
HETATM   31  C26 UNL     1      -5.738   1.438  -0.182  1.00  0.00           C  
HETATM   32  C27 UNL     1      -4.571  -1.329  -1.725  1.00  0.00           C  
HETATM   33  C28 UNL     1      -4.944  -2.384  -2.533  1.00  0.00           C  
HETATM   34  H1  UNL     1      -5.408  -4.719  -0.095  1.00  0.00           H  
HETATM   35  H2  UNL     1      -4.743  -2.816   1.266  1.00  0.00           H  
HETATM   36  H3  UNL     1      -3.814  -0.769   1.503  1.00  0.00           H  
HETATM   37  H4  UNL     1      -1.723  -0.824   1.142  1.00  0.00           H  
HETATM   38  H5  UNL     1      -2.339   0.680   1.867  1.00  0.00           H  
HETATM   39  H6  UNL     1      -0.016   0.843   1.275  1.00  0.00           H  
HETATM   40  H7  UNL     1      -1.012   2.104   0.540  1.00  0.00           H  
HETATM   41  H8  UNL     1       1.225   1.493  -2.120  1.00  0.00           H  
HETATM   42  H9  UNL     1       0.214   2.605  -1.157  1.00  0.00           H  
HETATM   43  H10 UNL     1       1.472   2.102   0.872  1.00  0.00           H  
HETATM   44  H11 UNL     1       2.561   2.544  -0.444  1.00  0.00           H  
HETATM   45  H12 UNL     1       3.931   1.035  -1.393  1.00  0.00           H  
HETATM   46  H13 UNL     1       4.401  -0.318  -0.326  1.00  0.00           H  
HETATM   47  H14 UNL     1       4.821   1.125   1.552  1.00  0.00           H  
HETATM   48  H15 UNL     1       4.208   2.587   0.751  1.00  0.00           H  
HETATM   49  H16 UNL     1       6.715   2.537   0.623  1.00  0.00           H  
HETATM   50  H17 UNL     1       6.071   2.266  -1.023  1.00  0.00           H  
HETATM   51  H18 UNL     1       7.577   0.654   1.934  1.00  0.00           H  
HETATM   52  H19 UNL     1       8.671  -1.519   1.865  1.00  0.00           H  
HETATM   53  H20 UNL     1       8.506  -2.956  -0.181  1.00  0.00           H  
HETATM   54  H21 UNL     1       7.234  -2.145  -2.098  1.00  0.00           H  
HETATM   55  H22 UNL     1       6.122   0.047  -2.047  1.00  0.00           H  
HETATM   56  H23 UNL     1       2.410  -0.617  -1.603  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.363  -1.498  -0.071  1.00  0.00           H  
HETATM   58  H25 UNL     1       0.132  -1.214   0.247  1.00  0.00           H  
HETATM   59  H26 UNL     1       0.235  -1.247  -1.535  1.00  0.00           H  
HETATM   60  H27 UNL     1      -5.602  -0.258   2.708  1.00  0.00           H  
HETATM   61  H28 UNL     1      -7.527   1.168   3.225  1.00  0.00           H  
HETATM   62  H29 UNL     1      -7.213   2.958  -0.576  1.00  0.00           H  
HETATM   63  H30 UNL     1      -5.244   1.516  -1.128  1.00  0.00           H  
HETATM   64  H31 UNL     1      -4.336  -0.381  -2.217  1.00  0.00           H  
HETATM   65  H32 UNL     1      -5.013  -2.304  -3.612  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   33
CONECT    3    4   34
CONECT    4    5    5   35
CONECT    5    6   32
CONECT    6    7   25   36
CONECT    7    8
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   11   24
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   23
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   18   22
CONECT   18   19   51
CONECT   19   20   20   52
CONECT   20   21   53
CONECT   21   22   22   54
CONECT   22   55
CONECT   23   24   56   57
CONECT   24   58   59
CONECT   25   26   26   31
CONECT   26   27   60
CONECT   27   28   28   61
CONECT   28   29   30
CONECT   30   31   31   62
CONECT   31   63
CONECT   32   33   33   64
CONECT   33   65
END

HMDB0259764
     RDKit          3D
Vanoxerine
 65 68  0  0  0  0  0  0  0  0999 V2000
   -5.6191   -4.6646   -2.7209 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422   -3.5957   -1.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1840   -3.7936   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8133   -2.7395    0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030   -1.4946   -0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1111   -0.3780    0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    0.3061   -0.0226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835    0.2384    0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881    1.0240    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879    0.6211   -0.7527 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7797    1.6326   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8481    1.7659   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5854    0.5408    0.0966 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9663    0.7114   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7267    1.6504    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1239    1.8107    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7795    0.4971   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4906    0.0435    1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1091   -1.1936    0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0121   -1.9750   -0.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2891   -1.4946   -1.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6758   -0.2712   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9889   -0.5804   -0.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5192   -0.6199   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2724    0.5271    0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9301    0.4524    1.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0125    1.2350    2.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4699    2.1461    1.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5470    2.9454    1.6287 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8323    2.2458    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7382    1.4380   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5712   -1.3289   -1.7253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9436   -2.3840   -2.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4084   -4.7193   -0.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7430   -2.8156    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8135   -0.7685    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.8242    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3386    0.6805    1.8674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164    0.8431    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0119    2.1041    0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252    1.4927   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2136    2.6050   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720    2.1017    0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5612    2.5444   -0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310    1.0348   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -0.3185   -0.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8214    1.1249    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084    2.5869    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146    2.5367    0.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0710    2.2664   -1.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5771    0.6541    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6714   -1.5186    1.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5058   -2.9563   -0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2337   -2.1448   -2.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1221    0.0470   -2.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097   -0.6167   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3628   -1.4977   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1321   -1.2141    0.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352   -1.2467   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020   -0.2579    2.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5269    1.1683    3.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2131    2.9578   -0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437    1.5164   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3362   -0.3805   -2.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0134   -2.3037   -3.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 13 23  1  0
 23 24  1  0
  6 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
  5 32  1  0
 32 33  2  0
 33  2  1  0
 24 10  1  0
 31 25  1  0
 22 17  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 18 51  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 30 62  1  0
 31 63  1  0
 32 64  1  0
 33 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
GBR 12909	ChEBI
GBR12909	ChEBI
Vanoxerina	ChEBI
Vanoxerinum	ChEBI
Vanoxeamine	MeSH
1-(2 (Bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine	MeSH
1-(2 (Bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride	MeSH

Chemical Formula

C₂₈H₃₂F₂N₂O

Average Molecular Weight

450.574

Monoisotopic Molecular Weight

450.248269984

IUPAC Name

1-{2-[bis(4-fluorophenyl)methoxy]ethyl}-4-(3-phenylpropyl)piperazine

Traditional Name

vanoxerine

CAS Registry Number

Not Available

SMILES

FC1=CC=C(C=C1)C(OCCN1CCN(CCCC2=CC=CC=C2)CC1)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C28H32F2N2O/c29-26-12-8-24(9-13-26)28(25-10-14-27(30)15-11-25)33-22-21-32-19-17-31(18-20-32)16-4-7-23-5-2-1-3-6-23/h1-3,5-6,8-15,28H,4,7,16-22H2

InChI Key

NAUWTFJOPJWYOT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Phenylpropylamine
Benzylether
Fluorobenzene
Halobenzene
Aralkylamine
N-alkylpiperazine
Aryl fluoride
Aryl halide
1,4-diazinane
Piperazine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:64089 )
tertiary amino compound (CHEBI:64089 )
ether (CHEBI:64089 )
N-alkylpiperazine (CHEBI:64089 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

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	4.9	ALOGPS
logP	6.24	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	8.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	15.71 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.38 m³·mol⁻¹	ChemAxon
Polarizability	49.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	212.587	32859911
AllCCS	[M+H-H2O]+	210.462	32859911
AllCCS	[M+Na]+	215.09	32859911
AllCCS	[M+NH4]+	214.535	32859911
AllCCS	[M-H]-	206.326	32859911
AllCCS	[M+Na-2H]-	206.617	32859911
AllCCS	[M+HCOO]-	207.099	32859911
DeepCCS	[M+H]+	205.999	30932474
DeepCCS	[M-H]-	203.642	30932474
DeepCCS	[M-2H]-	237.538	30932474
DeepCCS	[M+Na]+	212.75	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vanoxerine	FC1=CC=C(C=C1)C(OCCN1CCN(CCCC2=CC=CC=C2)CC1)C1=CC=C(F)C=C1	4308.7	Standard polar	33892256
Vanoxerine	FC1=CC=C(C=C1)C(OCCN1CCN(CCCC2=CC=CC=C2)CC1)C1=CC=C(F)C=C1	3204.5	Standard non polar	33892256
Vanoxerine	FC1=CC=C(C=C1)C(OCCN1CCN(CCCC2=CC=CC=C2)CC1)C1=CC=C(F)C=C1	3225.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vanoxerine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4194000000-344fe5131f2be1362489	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanoxerine 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 - Vanoxerine 10V, Positive-QTOF	splash10-0udi-0020900000-00bd29950987973f7c3b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanoxerine 20V, Positive-QTOF	splash10-0uyi-2595500000-3ee1c7bf802c3e64f6ae	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanoxerine 40V, Positive-QTOF	splash10-00kf-9740000000-96acadf78c51cd341f40	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanoxerine 10V, Negative-QTOF	splash10-0002-0030900000-af4306f4d98d60ace933	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanoxerine 20V, Negative-QTOF	splash10-00kb-0090600000-9374dc3a2108b8d82672	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanoxerine 40V, Negative-QTOF	splash10-014j-6390000000-6837a4e35ab5c6f28f54	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03701

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vanoxerine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

64089

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Vanoxerine (HMDB0259764)

MOL for HMDB0259764 (Vanoxerine)

3D MOL for HMDB0259764 (Vanoxerine)

3D SDF for HMDB0259764 (Vanoxerine)

3D-SDF for HMDB0259764 (Vanoxerine)

PDB for HMDB0259764 (Vanoxerine)

3D PDB for HMDB0259764 (Vanoxerine)

SMILES for HMDB0259764 (Vanoxerine)

INCHI for HMDB0259764 (Vanoxerine)

Structure for HMDB0259764 (Vanoxerine)

3D Structure for HMDB0259764 (Vanoxerine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra