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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (1) Show 12 proteins XML

enzymes (11)transporters (1) Show 12 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015232

Secondary Accession Numbers

HMDB15232

Metabolite Identification

Common Name

Pimozide

Description

Pimozide, also known as orap or halomonth, 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. Similarly to other typical antipsychotics pimozide has a high affinity for the Dopamine D2 receptor and this likely results in its sexual (due to prolactin hypersecretion) and extrapyramidal side effects as well as its therapeutic efficacy against the positive symptoms of schizophrenia. Pimozide is a drug which is used for the suppression of motor and phonic tics in patients with tourette's disorder who have failed to respond satisfactorily to standard treatment. It also has special neurologic indications for Tourette syndrome and resistant tics. Its use is advised against in individuals with people with either a personal or a family history of arrhythmias or torsades de pointes. Pimozide is a very strong basic compound (based on its pKa). Pimozide is a potentially toxic compound. However, patients who experience negative side-effects with the first line medications are typically given pimozide. Pimozide is used in its oral preparation in schizophrenia and chronic psychosis (on-label indications in Europe only), Tourette syndrome, and resistant tics (Europe, USA and Canada).

Structure

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

1100
  Mrv0541 02231215142D          

 34 38  0  0  0  0            999 V2000
    7.7808    4.6060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9596   -0.9870    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -3.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285   -0.4394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -2.7920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -4.1198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -2.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213   -0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    0.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6921    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484    1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7557    1.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0120    2.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3066    0.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4610    2.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1139    1.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8193    2.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7173    3.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6649    0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0755    3.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6013   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5246    3.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4086   -0.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 16  2  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  5 16  1  0  0  0  0
  6 16  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 17  1  0  0  0  0
 17 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 25  2  0  0  0  0
 20 27  1  0  0  0  0
 21 26  2  0  0  0  0
 21 28  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
 25 29  1  0  0  0  0
 26 30  1  0  0  0  0
 27 31  2  0  0  0  0
 28 32  2  0  0  0  0
 29 33  2  0  0  0  0
 30 34  2  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END

HMDB0015232
     RDKit          3D
Pimozide
 63 67  0  0  0  0  0  0  0  0999 V2000
    3.5549   -0.1025    2.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -0.3229    1.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073   -0.2096    1.9767 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6329   -0.5105    0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0055   -0.5579    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5599   -0.9076   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -1.2102   -1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3897   -1.1525   -1.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8012   -0.8049   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5026   -0.6915    0.2602 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.9193   -0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    0.3786   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368    1.1035   -0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    0.3396    0.3381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039    0.9210    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566    0.0284    1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259    0.6439    1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4029    0.9803    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6328   -0.1943   -0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8344   -1.4742   -0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0459   -2.5401   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -2.3312   -2.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -3.3863   -3.3425 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8548   -1.0479   -2.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435    0.0195   -2.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    1.5813    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1528    2.7188   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3909    3.2408    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2315    2.7026    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4639    3.2382    1.2659 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8136    1.5882    1.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727    1.0460    1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550   -1.0565    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659   -1.6942    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1831    0.0568    2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6041   -0.3207    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6501   -0.9450   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2025   -1.4882   -2.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756   -1.3937   -2.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6670   -1.5317   -1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.2419   -2.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7362    1.0293   -1.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    1.7628    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082    1.8338   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497    1.3126   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    1.8463    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461   -0.1683    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -0.9498    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -0.0625    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676    1.5622    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303    1.7697   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225   -1.6198    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1954   -3.5075   -0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8645   -0.8835   -4.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    1.0324   -2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4773    3.1196   -0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359    4.1236   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506    1.1459    2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2784    0.1630    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767   -1.4232    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523   -1.4560   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -2.7185   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6822   -1.9482    1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 14 33  1  0
 33 34  1  0
 10  2  1  0
 34 11  1  0
  9  4  1  0
 25 19  1  0
 32 26  1  0
  3 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 31 58  1  0
 32 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 34 63  1  0
M  END

1100
  Mrv0541 02231215142D          

 34 38  0  0  0  0            999 V2000
    7.7808    4.6060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9596   -0.9870    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -3.4559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285   -0.4394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -2.7920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -4.1198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -2.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213   -0.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    0.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6921    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484    1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7557    1.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0120    2.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3066    0.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4610    2.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1139    1.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8193    2.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0504    0.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7173    3.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6649    0.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0755    3.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6013   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5246    3.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4086   -0.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 16  2  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  7  1  0  0  0  0
  5 14  1  0  0  0  0
  5 16  1  0  0  0  0
  6 16  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 17  1  0  0  0  0
 17 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 25  2  0  0  0  0
 20 27  1  0  0  0  0
 21 26  2  0  0  0  0
 21 28  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
 25 29  1  0  0  0  0
 26 30  1  0  0  0  0
 27 31  2  0  0  0  0
 28 32  2  0  0  0  0
 29 33  2  0  0  0  0
 30 34  2  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015232

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1C(=O)NC2=CC=CC=C12)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)

> <INCHI_KEY>
YVUQSNJEYSNKRX-UHFFFAOYSA-N

> <FORMULA>
C28H29F2N3O

> <MOLECULAR_WEIGHT>
461.5462

> <EXACT_MASS>
461.227868975

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.0377572413355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one

> <ALOGPS_LOGP>
6.36

> <JCHEM_LOGP>
5.825713468

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.898585737602914

> <JCHEM_PKA_STRONGEST_BASIC>
8.383619699909323

> <JCHEM_POLAR_SURFACE_AREA>
35.580000000000005

> <JCHEM_REFRACTIVITY>
132.20780000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pimozide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015232
     RDKit          3D
Pimozide
 63 67  0  0  0  0  0  0  0  0999 V2000
    3.5549   -0.1025    2.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -0.3229    1.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073   -0.2096    1.9767 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6329   -0.5105    0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0055   -0.5579    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5599   -0.9076   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -1.2102   -1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3897   -1.1525   -1.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8012   -0.8049   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5026   -0.6915    0.2602 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.9193   -0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    0.3786   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368    1.1035   -0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    0.3396    0.3381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039    0.9210    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566    0.0284    1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259    0.6439    1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4029    0.9803    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6328   -0.1943   -0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8344   -1.4742   -0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0459   -2.5401   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -2.3312   -2.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -3.3863   -3.3425 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8548   -1.0479   -2.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435    0.0195   -2.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    1.5813    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1528    2.7188   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3909    3.2408    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2315    2.7026    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4639    3.2382    1.2659 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8136    1.5882    1.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727    1.0460    1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550   -1.0565    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659   -1.6942    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1831    0.0568    2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6041   -0.3207    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6501   -0.9450   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2025   -1.4882   -2.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756   -1.3937   -2.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6670   -1.5317   -1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.2419   -2.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7362    1.0293   -1.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    1.7628    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082    1.8338   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497    1.3126   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    1.8463    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461   -0.1683    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -0.9498    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -0.0625    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676    1.5622    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303    1.7697   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225   -1.6198    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1954   -3.5075   -0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8645   -0.8835   -4.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    1.0324   -2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4773    3.1196   -0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359    4.1236   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506    1.1459    2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2784    0.1630    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767   -1.4232    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523   -1.4560   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -2.7185   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6822   -1.9482    1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 14 33  1  0
 33 34  1  0
 10  2  1  0
 34 11  1  0
  9  4  1  0
 25 19  1  0
 32 26  1  0
  3 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 31 58  1  0
 32 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 34 63  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1100                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0      14.524   8.598   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0      16.725  -1.842   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       9.643  -6.451   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.640  -0.820   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.205  -5.212   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.205  -7.690   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.683  -3.748   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.190  -3.430   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.654  -2.602   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.668  -1.967   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.133  -1.138   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.118   0.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.625   0.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747  -5.681   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.104   2.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.103  -6.451   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.611   2.743   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -7.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -4.911   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.089   4.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.639   1.596   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -7.991   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -5.681   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080  -7.221   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.061   5.353   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.146   1.914   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.596   4.524   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.161   0.133   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.539   6.817   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.174   0.768   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.074   5.988   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.189  -1.014   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.046   7.134   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.696  -0.696   0.000  0.00  0.00           C+0
CONECT    1   33                                                            
CONECT    2   34                                                            
CONECT    3   16                                                            
CONECT    4   10   11   12                                                  
CONECT    5    7   14   16                                                  
CONECT    6   16   18                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    4    8                                                       
CONECT   11    4    9                                                       
CONECT   12    4   13                                                       
CONECT   13   12   15                                                       
CONECT   14    5   18   19                                                  
CONECT   15   13   17                                                       
CONECT   16    3    5    6                                                  
CONECT   17   15   20   21                                                  
CONECT   18    6   14   22                                                  
CONECT   19   14   23                                                       
CONECT   20   17   25   27                                                  
CONECT   21   17   26   28                                                  
CONECT   22   18   24                                                       
CONECT   23   19   24                                                       
CONECT   24   22   23                                                       
CONECT   25   20   29                                                       
CONECT   26   21   30                                                       
CONECT   27   20   31                                                       
CONECT   28   21   32                                                       
CONECT   29   25   33                                                       
CONECT   30   26   34                                                       
CONECT   31   27   33                                                       
CONECT   32   28   34                                                       
CONECT   33    1   29   31                                                  
CONECT   34    2   30   32                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    HMDB0015232
HETATM    1  O1  UNL     1       3.555  -0.102   2.306  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.538  -0.323   1.554  1.00  0.00           C  
HETATM    3  N1  UNL     1       5.807  -0.210   1.977  1.00  0.00           N  
HETATM    4  C2  UNL     1       6.633  -0.511   0.938  1.00  0.00           C  
HETATM    5  C3  UNL     1       8.006  -0.558   0.799  1.00  0.00           C  
HETATM    6  C4  UNL     1       8.560  -0.908  -0.416  1.00  0.00           C  
HETATM    7  C5  UNL     1       7.756  -1.210  -1.494  1.00  0.00           C  
HETATM    8  C6  UNL     1       6.390  -1.152  -1.319  1.00  0.00           C  
HETATM    9  C7  UNL     1       5.801  -0.805  -0.111  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.503  -0.692   0.260  1.00  0.00           N  
HETATM   11  C8  UNL     1       3.307  -0.919  -0.561  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.838   0.379  -1.155  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.837   1.104  -0.336  1.00  0.00           C  
HETATM   14  N3  UNL     1       0.875   0.340   0.338  1.00  0.00           N  
HETATM   15  C11 UNL     1      -0.404   0.921   0.515  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.357   0.028   1.243  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.726   0.644   1.440  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.403   0.980   0.156  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.633  -0.194  -0.736  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.834  -1.474  -0.262  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.046  -2.540  -1.130  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.058  -2.331  -2.496  1.00  0.00           C  
HETATM   23  F1  UNL     1      -4.267  -3.386  -3.343  1.00  0.00           F  
HETATM   24  C19 UNL     1      -3.855  -1.048  -2.950  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.644   0.019  -2.098  1.00  0.00           C  
HETATM   26  C21 UNL     1      -4.727   1.581   0.447  1.00  0.00           C  
HETATM   27  C22 UNL     1      -5.153   2.719  -0.254  1.00  0.00           C  
HETATM   28  C23 UNL     1      -6.391   3.241   0.040  1.00  0.00           C  
HETATM   29  C24 UNL     1      -7.232   2.703   0.987  1.00  0.00           C  
HETATM   30  F2  UNL     1      -8.464   3.238   1.266  1.00  0.00           F  
HETATM   31  C25 UNL     1      -6.814   1.588   1.673  1.00  0.00           C  
HETATM   32  C26 UNL     1      -5.573   1.046   1.394  1.00  0.00           C  
HETATM   33  C27 UNL     1       0.955  -1.057   0.350  1.00  0.00           C  
HETATM   34  C28 UNL     1       2.266  -1.694   0.151  1.00  0.00           C  
HETATM   35  H1  UNL     1       6.183   0.057   2.919  1.00  0.00           H  
HETATM   36  H2  UNL     1       8.604  -0.321   1.644  1.00  0.00           H  
HETATM   37  H3  UNL     1       9.650  -0.945  -0.526  1.00  0.00           H  
HETATM   38  H4  UNL     1       8.203  -1.488  -2.461  1.00  0.00           H  
HETATM   39  H5  UNL     1       5.776  -1.394  -2.177  1.00  0.00           H  
HETATM   40  H6  UNL     1       3.667  -1.532  -1.418  1.00  0.00           H  
HETATM   41  H7  UNL     1       2.443   0.242  -2.189  1.00  0.00           H  
HETATM   42  H8  UNL     1       3.736   1.029  -1.263  1.00  0.00           H  
HETATM   43  H9  UNL     1       2.374   1.763   0.396  1.00  0.00           H  
HETATM   44  H10 UNL     1       1.308   1.834  -1.018  1.00  0.00           H  
HETATM   45  H11 UNL     1      -0.850   1.313  -0.441  1.00  0.00           H  
HETATM   46  H12 UNL     1      -0.286   1.846   1.153  1.00  0.00           H  
HETATM   47  H13 UNL     1      -0.946  -0.168   2.255  1.00  0.00           H  
HETATM   48  H14 UNL     1      -1.415  -0.950   0.725  1.00  0.00           H  
HETATM   49  H15 UNL     1      -3.315  -0.063   2.022  1.00  0.00           H  
HETATM   50  H16 UNL     1      -2.568   1.562   2.036  1.00  0.00           H  
HETATM   51  H17 UNL     1      -2.830   1.770  -0.415  1.00  0.00           H  
HETATM   52  H18 UNL     1      -3.822  -1.620   0.818  1.00  0.00           H  
HETATM   53  H19 UNL     1      -4.195  -3.508  -0.677  1.00  0.00           H  
HETATM   54  H20 UNL     1      -3.864  -0.884  -4.022  1.00  0.00           H  
HETATM   55  H21 UNL     1      -3.484   1.032  -2.467  1.00  0.00           H  
HETATM   56  H22 UNL     1      -4.477   3.120  -0.989  1.00  0.00           H  
HETATM   57  H23 UNL     1      -6.736   4.124  -0.495  1.00  0.00           H  
HETATM   58  H24 UNL     1      -7.451   1.146   2.419  1.00  0.00           H  
HETATM   59  H25 UNL     1      -5.278   0.163   1.952  1.00  0.00           H  
HETATM   60  H26 UNL     1       0.477  -1.423   1.309  1.00  0.00           H  
HETATM   61  H27 UNL     1       0.252  -1.456  -0.444  1.00  0.00           H  
HETATM   62  H28 UNL     1       2.114  -2.718  -0.307  1.00  0.00           H  
HETATM   63  H29 UNL     1       2.682  -1.948   1.174  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4   35
CONECT    4    5    5    9
CONECT    5    6   36
CONECT    6    7    7   37
CONECT    7    8   38
CONECT    8    9    9   39
CONECT    9   10
CONECT   10   11
CONECT   11   12   34   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   33
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   26   51
CONECT   19   20   20   25
CONECT   20   21   52
CONECT   21   22   22   53
CONECT   22   23   24
CONECT   24   25   25   54
CONECT   25   55
CONECT   26   27   27   32
CONECT   27   28   56
CONECT   28   29   29   57
CONECT   29   30   31
CONECT   31   32   32   58
CONECT   32   59
CONECT   33   34   60   61
CONECT   34   62   63
END

HMDB0015232
     RDKit          3D
Pimozide
 63 67  0  0  0  0  0  0  0  0999 V2000
    3.5549   -0.1025    2.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5380   -0.3229    1.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073   -0.2096    1.9767 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6329   -0.5105    0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0055   -0.5579    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5599   -0.9076   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7560   -1.2102   -1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3897   -1.1525   -1.3190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8012   -0.8049   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5026   -0.6915    0.2602 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.9193   -0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    0.3786   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8368    1.1035   -0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751    0.3396    0.3381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4039    0.9210    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566    0.0284    1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7259    0.6439    1.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4029    0.9803    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6328   -0.1943   -0.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8344   -1.4742   -0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0459   -2.5401   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -2.3312   -2.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667   -3.3863   -3.3425 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8548   -1.0479   -2.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6435    0.0195   -2.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274    1.5813    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1528    2.7188   -0.2544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3909    3.2408    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2315    2.7026    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4639    3.2382    1.2659 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8136    1.5882    1.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727    1.0460    1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550   -1.0565    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659   -1.6942    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1831    0.0568    2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6041   -0.3207    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6501   -0.9450   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2025   -1.4882   -2.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7756   -1.3937   -2.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6670   -1.5317   -1.4180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4430    0.2419   -2.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7362    1.0293   -1.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3738    1.7628    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3082    1.8338   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497    1.3126   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    1.8463    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461   -0.1683    2.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -0.9498    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -0.0625    2.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676    1.5622    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303    1.7697   -0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225   -1.6198    0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1954   -3.5075   -0.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8645   -0.8835   -4.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839    1.0324   -2.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4773    3.1196   -0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359    4.1236   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4506    1.1459    2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2784    0.1630    1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767   -1.4232    1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523   -1.4560   -0.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -2.7185   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6822   -1.9482    1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  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  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 18 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  2  0
 14 33  1  0
 33 34  1  0
 10  2  1  0
 34 11  1  0
  9  4  1  0
 25 19  1  0
 32 26  1  0
  3 35  1  0
  5 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 31 58  1  0
 32 59  1  0
 33 60  1  0
 33 61  1  0
 34 62  1  0
 34 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Halomonth	ChEBI
Neoperidole	ChEBI
Opiran	ChEBI
Orap	ChEBI
Pimozida	ChEBI
Pimozidum	ChEBI
Janssen brand OF pimozide	HMDB
Pharmascience brand OF pimozide	HMDB
Orap forte	HMDB
ASTA medica brand OF pimozide	HMDB
Antalon	HMDB

Chemical Formula

C₂₈H₂₉F₂N₃O

Average Molecular Weight

461.5462

Monoisotopic Molecular Weight

461.227868975

IUPAC Name

1-{1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl}-2,3-dihydro-1H-1,3-benzodiazol-2-one

Traditional Name

pimozide

CAS Registry Number

2062-78-4

SMILES

FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1C(=O)NC2=CC=CC=C12)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C28H29F2N3O/c29-22-11-7-20(8-12-22)25(21-9-13-23(30)14-10-21)4-3-17-32-18-15-24(16-19-32)33-27-6-2-1-5-26(27)31-28(33)34/h1-2,5-14,24-25H,3-4,15-19H2,(H,31,34)

InChI Key

YVUQSNJEYSNKRX-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
Phenylbutylamine
Benzimidazole
Aralkylamine
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Piperidine
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organooxygen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organofluoride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:8212 )
benzimidazoles (CHEBI:8212 )
heteroarylpiperidine (CHEBI:8212 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015232)

Source

Exogenous

Exogenous (HMDB: HMDB0015232)

Process

Not Available

Role

Industrial application

H1-receptor antagonist (HMDB: HMDB0015232)
Serotonergic antagonist (HMDB: HMDB0015232)
First generation antipsychotic (HMDB: HMDB0015232)
Antidyskinesia agent (HMDB: HMDB0015232)

Dopamine uptake inhibitor (HMDB: HMDB0015232)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	214 - 218 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0017 g/L	Not Available
LogP	5.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	214.4	30932474
[M+H]+	Not Available	212.625	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000779

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	6.36	ALOGPS
logP	5.83	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	12.9	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.58 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.21 m³·mol⁻¹	ChemAxon
Polarizability	50.04 Å³	ChemAxon
Number of Rings	5	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
DeepCCS	[M-2H]-	239.064	30932474
DeepCCS	[M+Na]+	215.356	30932474
AllCCS	[M+H]+	212.9	32859911
AllCCS	[M+H-H2O]+	210.9	32859911
AllCCS	[M+NH4]+	214.8	32859911
AllCCS	[M+Na]+	215.3	32859911
AllCCS	[M-H]-	206.6	32859911
AllCCS	[M+Na-2H]-	206.9	32859911
AllCCS	[M+HCOO]-	207.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.43 minutes	32390414
Predicted by Siyang on May 30, 2022	13.9259 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.57 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1993.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	257.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	234.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	619.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	561.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	151.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1365.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	557.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1533.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	297.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	211.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pimozide	FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1C(=O)NC2=CC=CC=C12)C1=CC=C(F)C=C1	4641.3	Standard polar	33892256
Pimozide	FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1C(=O)NC2=CC=CC=C12)C1=CC=C(F)C=C1	3440.5	Standard non polar	33892256
Pimozide	FC1=CC=C(C=C1)C(CCCN1CCC(CC1)N1C(=O)NC2=CC=CC=C12)C1=CC=C(F)C=C1	3970.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pimozide,1TMS,isomer #1	C[Si](C)(C)N1C(=O)N(C2CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C2=CC=CC=C21	3774.5	Semi standard non polar	33892256
Pimozide,1TMS,isomer #1	C[Si](C)(C)N1C(=O)N(C2CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C2=CC=CC=C21	3251.4	Standard non polar	33892256
Pimozide,1TMS,isomer #1	C[Si](C)(C)N1C(=O)N(C2CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C2=CC=CC=C21	4348.5	Standard polar	33892256
Pimozide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N(C2CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C2=CC=CC=C21	3931.9	Semi standard non polar	33892256
Pimozide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N(C2CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C2=CC=CC=C21	3401.1	Standard non polar	33892256
Pimozide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)N(C2CCN(CCCC(C3=CC=C(F)C=C3)C3=CC=C(F)C=C3)CC2)C2=CC=CC=C21	4364.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pimozide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ugi-1391000000-81a5491e04c0772aa266	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pimozide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-4890100000-ff909df45204eac82c46	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide , positive-QTOF	splash10-03fr-3945500000-63d831a19fe77286e9e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 90V, Positive-QTOF	splash10-0a4i-2900000000-c5c24c6004ad63c44b7b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 75V, Positive-QTOF	splash10-0a4i-2900000000-4ec6383bd789926aace8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 45V, Negative-QTOF	splash10-001i-0900000000-f7e5bc8b3118f019d29a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 60V, Negative-QTOF	splash10-001i-0900000000-15ed37cc4150d726424f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 60V, Positive-QTOF	splash10-0a4j-2900000000-4cb696b16013c21eaecc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 45V, Positive-QTOF	splash10-054k-3922000000-3dece675311cfc7dcecb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 15V, Positive-QTOF	splash10-03di-0000900000-a6c11637d319ae7e0d4b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 30V, Positive-QTOF	splash10-03di-0001900000-e11e7746c656531d49c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pimozide 90V, Negative-QTOF	splash10-001i-0900000000-a10c36c7b309fd6a144a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 10V, Positive-QTOF	splash10-03di-0010900000-930a125974bd00e0c2eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 20V, Positive-QTOF	splash10-03dj-0292700000-2985b790e5501b39bbd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 40V, Positive-QTOF	splash10-00ks-2981100000-75644e2a4fa99f98d3bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 10V, Negative-QTOF	splash10-03di-0000900000-d214f454d376b4403edd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 20V, Negative-QTOF	splash10-03e9-0410900000-0d1a6255c713f6209ad8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 40V, Negative-QTOF	splash10-001i-2920000000-0b02fc753cd5d50662e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 10V, Positive-QTOF	splash10-03di-0000900000-1007eb55b47c59016fd5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 20V, Positive-QTOF	splash10-03di-0001900000-6016ca53ea77d615c57c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 40V, Positive-QTOF	splash10-03yj-2790700000-5ee4d094cbf2edb564c4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 10V, Negative-QTOF	splash10-03di-0000900000-d24101b35641ce78a840	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 20V, Negative-QTOF	splash10-03xr-1000900000-a8261095a6ae4bd8e429	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pimozide 40V, Negative-QTOF	splash10-001i-3911100000-2bfbcbf4417742b7624d	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01100	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01100	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01100

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

15520

KEGG Compound ID

C07566

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pimozide

METLIN ID

Not Available

PubChem Compound

16362

PDB ID

Not Available

ChEBI ID

8212

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

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

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

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

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

Enzyme Details

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

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

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

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

Enzyme Details

5. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

6. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

7. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

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

Enzyme Details

8. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
Silva MR, Bernardi MM, Cruz-Casallas PE, Felicio LF: Pimozide injections into the Nucleus accumbens disrupt maternal behaviour in lactating rats. Pharmacol Toxicol. 2003 Jul;93(1):42-7. [PubMed:12828573 ]
Muscat R, Sampson D, Willner P: Dopaminergic mechanism of imipramine action in an animal model of depression. Biol Psychiatry. 1990 Aug 1;28(3):223-30. [PubMed:2378927 ]
Zarrindast MR, Heidari MR: On the mechanisms by which theophylline changes core body temperature in mice. Eur J Pharmacol. 1994 May 12;257(1-2):13-20. [PubMed:8082693 ]
Freedman SB, Patel S, Marwood R, Emms F, Seabrook GR, Knowles MR, McAllister G: Expression and pharmacological characterization of the human D3 dopamine receptor. J Pharmacol Exp Ther. 1994 Jan;268(1):417-26. [PubMed:8301582 ]
Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. [PubMed:7855217 ]
Murphy LL, Adrian BA, Kohli M: Inhibition of luteinizing hormone secretion by delta9-tetrahydrocannabinol in the ovariectomized rat: effect of pretreatment with neurotransmitter or neuropeptide receptor antagonists. Steroids. 1999 Sep;64(9):664-71. [PubMed:10503726 ]

Enzyme Details

9. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Papadopoulos V, Brown AS, Hall PF: Calcium-calmodulin-dependent phosphorylation of cytoskeletal proteins from adrenal cells. Mol Cell Endocrinol. 1990 Dec 3;74(2):109-23. [PubMed:1965307 ]
Wang XB, Sato N, Greer MA, Greer SE, McAdams S: Role of extracellular calcium and calmodulin in prolactin secretion induced by hyposmolarity, thyrotropin-releasing hormone, and high K+ in GH4C1 cells. Acta Endocrinol (Copenh). 1990 Aug;123(2):218-24. [PubMed:2120879 ]
Strobl JS, Kirkwood KL, Lantz TK, Lewine MA, Peterson VA, Worley JF 3rd: Inhibition of human breast cancer cell proliferation in tissue culture by the neuroleptic agents pimozide and thioridazine. Cancer Res. 1990 Sep 1;50(17):5399-405. [PubMed:2386945 ]
Cimino M, Weiss B: Characteristics of the binding of phenoxybenzamine to calmodulin. Biochem Pharmacol. 1988 Jul 15;37(14):2739-45. [PubMed:3134891 ]
Mody I, Baimbridge KG, Miller JJ: Blockade of tetanic- and calcium-induced long-term potentiation in the hippocampal slice preparation by neuroleptics. Neuropharmacology. 1984 Jun;23(6):625-31. [PubMed:6146939 ]

Enzyme Details

10. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Kang J, Wang L, Cai F, Rampe D: High affinity blockade of the HERG cardiac K(+) channel by the neuroleptic pimozide. Eur J Pharmacol. 2000 Mar 31;392(3):137-40. [PubMed:10762666 ]
Osypenko VM, Degtiar VIe, Naid'onov VG, Shuba IaM: [Blockade of HERG K+ channels expressed in Xenopus oocytes by antipsychotic agents]. Fiziol Zh. 2001;47(1):17-25. [PubMed:11296551 ]
Shuba YM, Degtiar VE, Osipenko VN, Naidenov VG, Woosley RL: Testosterone-mediated modulation of HERG blockade by proarrhythmic agents. Biochem Pharmacol. 2001 Jul 1;62(1):41-9. [PubMed:11377395 ]
Kang J, Chen XL, Rampe D: The antipsychotic drugs sertindole and pimozide block erg3, a human brain K(+) channel. Biochem Biophys Res Commun. 2001 Aug 24;286(3):499-504. [PubMed:11511086 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389 ]
Ibrahim S, Peggins J, Knapton A, Licht T, Aszalos A: Influence of antipsychotic, antiemetic, and Ca(2+) channel blocker drugs on the cellular accumulation of the anticancer drug daunorubicin: P-glycoprotein modulation. J Pharmacol Exp Ther. 2000 Dec;295(3):1276-83. [PubMed:11082465 ]

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Showing metabocard for Pimozide (HMDB0015232)

MOL for HMDB0015232 (Pimozide)

3D MOL for HMDB0015232 (Pimozide)

3D SDF for HMDB0015232 (Pimozide)

3D-SDF for HMDB0015232 (Pimozide)

PDB for HMDB0015232 (Pimozide)

3D PDB for HMDB0015232 (Pimozide)

SMILES for HMDB0015232 (Pimozide)

INCHI for HMDB0015232 (Pimozide)

Structure for HMDB0015232 (Pimozide)

3D Structure for HMDB0015232 (Pimozide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References