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Showing metabocard for Cisapride (HMDB0014742)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (14) Show 14 proteinsXML
enzymes (14) Show 14 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:43 UTC
HMDB IDHMDB0014742
Secondary Accession Numbers
  • HMDB14742
Metabolite Identification
Common NameCisapride
DescriptionCisapride, also known as (+-)-cisapride or cisapridum, belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring. Cisapride is a drug which is used for the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease. Cisapride is a very strong basic compound (based on its pKa). Cisapride is a potentially toxic compound.
Structure
Data?1582753216
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014742 (Cisapride)


  Mrv0541 04191212132D          

 32 34  0  0  1  0            999 V2000
    7.7581   -7.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4726   -6.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0436   -6.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1789   -7.2858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7581   -8.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -7.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1781   -8.1108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0436   -8.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8922   -8.5240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3292   -8.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1766   -9.7608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8914   -9.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4633   -8.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4726   -6.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4625   -9.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6147   -8.5282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0436   -9.3532    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0436   -6.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4634   -9.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6071   -8.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0337  -10.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1783   -9.3532    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7493   -9.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4626  -10.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0345   -9.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7477  -11.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1758  -10.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8899  -10.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3188  -11.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6047  -10.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -5.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3211   -8.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  5  1  2  0  0  0  0
  4  2  1  0  0  0  0
 14  2  2  0  0  0  0
  6  3  2  0  0  0  0
 18  3  1  0  0  0  0
  7  4  1  1  0  0  0
  8  5  1  0  0  0  0
 10  6  1  0  0  0  0
  9  7  1  0  0  0  0
 13  7  1  0  0  0  0
 10  8  2  0  0  0  0
 17  8  1  0  0  0  0
 12  9  1  0  0  0  0
  9 20  1  1  0  0  0
 16 10  1  0  0  0  0
 15 11  1  0  0  0  0
 27 11  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 31 18  1  0  0  0  0
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 29 21  1  0  0  0  0
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 25 23  1  0  0  0  0
 26 24  2  0  0  0  0
 28 27  1  0  0  0  0
 30 28  1  0  0  0  0
 30 29  1  0  0  0  0
M  END
Download

3D MOL for HMDB0014742 (Cisapride)

HMDB0014742
     RDKit          3D
Cisapride
 61 63  0  0  0  0  0  0  0  0999 V2000
   -5.6573    1.5891   -0.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8356    0.8186   -0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2927   -0.0330    0.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6660   -0.1819    1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1783   -1.0155    2.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5627   -1.1967    2.3369 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2847   -1.7402    2.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8819   -2.8360    4.1137 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9375   -1.6009    2.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -0.7464    1.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565   -0.6460    1.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -1.3941    2.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550    0.1808    0.6535 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911    0.1392    0.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2297    1.4907    1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373    2.0588   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    1.1646   -0.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244    1.6982   -1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352    1.2790   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505   -0.1682   -1.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5242   -0.4959   -1.9378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4431   -0.3850   -0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553   -0.0002    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1653    0.1013    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4656   -0.1784    0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4828   -0.0952    1.8856 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7754   -0.5743   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7675   -0.6643   -1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331   -0.1226   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -0.1836   -0.7075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8222    0.7022   -1.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303    0.1195   -2.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0706    1.9438   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2322   -2.1625    3.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4831   -0.6101    1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475    2.1811    1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    1.3793    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516    2.5501   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    2.9215    0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    2.8390   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    1.4428   -2.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520    1.7826   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091    1.7280   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524   -0.7314   -0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529   -0.5395   -2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1382    0.2071    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8890    0.4070    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8001   -0.7907   -0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0243   -0.9733   -2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6338   -0.8280    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -0.4474   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -1.2466   -0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    0.9460   -3.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4854   -0.4301   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368   -0.5451   -3.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
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 24 25  2  0
 25 26  1  0
 25 27  1  0
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 17 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 10  3  1  0
 30 14  1  0
 28 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  9 39  1  0
 13 40  1  0
 14 41  1  1
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
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 20 50  1  0
 20 51  1  0
 23 52  1  0
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 29 56  1  0
 29 57  1  0
 30 58  1  6
 32 59  1  0
 32 60  1  0
 32 61  1  0
M  END
Download

3D SDF for HMDB0014742 (Cisapride)


  Mrv0541 04191212132D          

 32 34  0  0  1  0            999 V2000
    7.7581   -7.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4726   -6.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0436   -6.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1789   -7.2858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7581   -8.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -7.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1781   -8.1108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0436   -8.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8922   -8.5240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3292   -8.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1766   -9.7608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8914   -9.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4633   -8.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4726   -6.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4625   -9.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6147   -8.5282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0436   -9.3532    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0436   -6.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4634   -9.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6071   -8.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0337  -10.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1783   -9.3532    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7493   -9.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4626  -10.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0345   -9.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7477  -11.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1758  -10.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8899  -10.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3188  -11.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6047  -10.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -5.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3211   -8.5254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  5  1  2  0  0  0  0
  4  2  1  0  0  0  0
 14  2  2  0  0  0  0
  6  3  2  0  0  0  0
 18  3  1  0  0  0  0
  7  4  1  1  0  0  0
  8  5  1  0  0  0  0
 10  6  1  0  0  0  0
  9  7  1  0  0  0  0
 13  7  1  0  0  0  0
 10  8  2  0  0  0  0
 17  8  1  0  0  0  0
 12  9  1  0  0  0  0
  9 20  1  1  0  0  0
 16 10  1  0  0  0  0
 15 11  1  0  0  0  0
 27 11  1  0  0  0  0
 12 11  1  0  0  0  0
 15 13  1  0  0  0  0
 31 18  1  0  0  0  0
 24 19  1  0  0  0  0
 22 19  1  0  0  0  0
 23 19  2  0  0  0  0
 32 20  1  0  0  0  0
 29 21  1  0  0  0  0
 25 21  2  0  0  0  0
 26 21  1  0  0  0  0
 25 23  1  0  0  0  0
 26 24  2  0  0  0  0
 28 27  1  0  0  0  0
 30 28  1  0  0  0  0
 30 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014742

> <DATABASE_NAME>
hmdb

> <SMILES>
CO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1

> <INCHI_KEY>
DCSUBABJRXZOMT-IRLDBZIGSA-N

> <FORMULA>
C23H29ClFN3O4

> <MOLECULAR_WEIGHT>
465.945

> <EXACT_MASS>
465.183062343

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
49.11181362713439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.491358864666666

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.768892546739217

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.575677583907808

> <JCHEM_PKA_STRONGEST_BASIC>
8.239418549799563

> <JCHEM_POLAR_SURFACE_AREA>
86.05000000000001

> <JCHEM_REFRACTIVITY>
122.9349

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-cisapride

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0014742 (Cisapride)

HMDB0014742
     RDKit          3D
Cisapride
 61 63  0  0  0  0  0  0  0  0999 V2000
   -5.6573    1.5891   -0.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8356    0.8186   -0.0517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2927   -0.0330    0.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6660   -0.1819    1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1783   -1.0155    2.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5627   -1.1967    2.3369 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2847   -1.7402    2.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8819   -2.8360    4.1137 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9375   -1.6009    2.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978   -0.7464    1.6918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565   -0.6460    1.5574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -1.3941    2.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2550    0.1808    0.6535 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911    0.1392    0.6705 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2297    1.4907    1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6373    2.0588   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    1.1646   -0.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5244    1.6982   -1.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352    1.2790   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505   -0.1682   -1.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5242   -0.4959   -1.9378 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4431   -0.3850   -0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553   -0.0002    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1653    0.1013    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4656   -0.1784    0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4828   -0.0952    1.8856 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7754   -0.5743   -0.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7675   -0.6643   -1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2331   -0.1226   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655   -0.1836   -0.7075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8222    0.7022   -1.5958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303    0.1195   -2.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0706    1.9438   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5466    1.0319   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9745    2.5476   -0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3305    0.3884    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0060   -0.9107    3.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1525   -1.6257    1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2322   -2.1625    3.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7102    0.8135   -0.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4831   -0.6101    1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475    2.1811    1.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    1.3793    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516    2.5501   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851    2.9215    0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    2.8390   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    1.4428   -2.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520    1.7826   -2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091    1.7280   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7524   -0.7314   -0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529   -0.5395   -2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1382    0.2071    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8890    0.4070    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8001   -0.7907   -0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0243   -0.9733   -2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6338   -0.8280    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -0.4474   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -1.2466   -0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0144    0.9460   -3.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4854   -0.4301   -2.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368   -0.5451   -3.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 10  3  1  0
 30 14  1  0
 28 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  9 39  1  0
 13 40  1  0
 14 41  1  1
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 23 52  1  0
 24 53  1  0
 27 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  6
 32 59  1  0
 32 60  1  0
 32 61  1  0
M  END
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PDB for HMDB0014742 (Cisapride)

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      14.482 -13.609   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.816 -12.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.148 -12.839   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      17.134 -13.600   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      14.482 -15.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.815 -13.609   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.132 -15.140   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.148 -15.919   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.465 -15.911   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.815 -15.149   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      17.130 -18.220   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      18.464 -17.451   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.798 -15.909   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      15.816 -11.299   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.797 -17.449   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      10.481 -15.919   0.000  0.00  0.00           N+0
HETATM   17 Cl   UNK     0      13.148 -17.459   0.000  0.00  0.00          Cl+0
HETATM   18  O   UNK     0      13.148 -11.299   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      25.132 -18.228   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      19.800 -15.143   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      22.463 -19.765   0.000  0.00  0.00           C+0
HETATM   22  F   UNK     0      26.466 -17.459   0.000  0.00  0.00           F+0
HETATM   23  C   UNK     0      23.799 -17.457   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.130 -19.768   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.464 -18.225   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.796 -20.537   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.128 -19.760   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.461 -20.531   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      21.128 -20.534   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      19.795 -19.763   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.815 -10.529   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.133 -15.914   0.000  0.00  0.00           C+0
CONECT    1    2    3    5                                                  
CONECT    2    1    4   14                                                  
CONECT    3    1    6   18                                                  
CONECT    4    2    7                                                       
CONECT    5    1    8                                                       
CONECT    6    3   10                                                       
CONECT    7    4    9   13                                                  
CONECT    8    5   10   17                                                  
CONECT    9    7   12   20                                                  
CONECT   10    6    8   16                                                  
CONECT   11   15   27   12                                                  
CONECT   12    9   11                                                       
CONECT   13    7   15                                                       
CONECT   14    2                                                            
CONECT   15   11   13                                                       
CONECT   16   10                                                            
CONECT   17    8                                                            
CONECT   18    3   31                                                       
CONECT   19   24   22   23                                                  
CONECT   20    9   32                                                       
CONECT   21   29   25   26                                                  
CONECT   22   19                                                            
CONECT   23   19   25                                                       
CONECT   24   19   26                                                       
CONECT   25   21   23                                                       
CONECT   26   21   24                                                       
CONECT   27   11   28                                                       
CONECT   28   27   30                                                       
CONECT   29   21   30                                                       
CONECT   30   28   29                                                       
CONECT   31   18                                                            
CONECT   32   20                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END
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3D PDB for HMDB0014742 (Cisapride)

COMPND    HMDB0014742
HETATM    1  C1  UNL     1      -5.657   1.589  -0.891  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.836   0.819  -0.052  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.293  -0.033   0.921  1.00  0.00           C  
HETATM    4  C3  UNL     1      -6.666  -0.182   1.133  1.00  0.00           C  
HETATM    5  C4  UNL     1      -7.178  -1.016   2.083  1.00  0.00           C  
HETATM    6  N1  UNL     1      -8.563  -1.197   2.337  1.00  0.00           N  
HETATM    7  C5  UNL     1      -6.285  -1.740   2.866  1.00  0.00           C  
HETATM    8 CL1  UNL     1      -6.882  -2.836   4.114  1.00  0.00          CL  
HETATM    9  C6  UNL     1      -4.937  -1.601   2.667  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.398  -0.746   1.692  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.957  -0.646   1.557  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.269  -1.394   2.349  1.00  0.00           O  
HETATM   13  N2  UNL     1      -2.255   0.181   0.654  1.00  0.00           N  
HETATM   14  C9  UNL     1      -0.791   0.139   0.670  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.230   1.491   1.050  1.00  0.00           C  
HETATM   16  C11 UNL     1       0.637   2.059  -0.026  1.00  0.00           C  
HETATM   17  N3  UNL     1       1.742   1.165  -0.371  1.00  0.00           N  
HETATM   18  C12 UNL     1       2.524   1.698  -1.435  1.00  0.00           C  
HETATM   19  C13 UNL     1       3.935   1.279  -1.589  1.00  0.00           C  
HETATM   20  C14 UNL     1       4.150  -0.168  -1.803  1.00  0.00           C  
HETATM   21  O3  UNL     1       5.524  -0.496  -1.938  1.00  0.00           O  
HETATM   22  C15 UNL     1       6.443  -0.385  -0.949  1.00  0.00           C  
HETATM   23  C16 UNL     1       6.155  -0.000   0.335  1.00  0.00           C  
HETATM   24  C17 UNL     1       7.165   0.101   1.296  1.00  0.00           C  
HETATM   25  C18 UNL     1       8.466  -0.178   0.994  1.00  0.00           C  
HETATM   26  F1  UNL     1       9.483  -0.095   1.886  1.00  0.00           F  
HETATM   27  C19 UNL     1       8.775  -0.574  -0.313  1.00  0.00           C  
HETATM   28  C20 UNL     1       7.768  -0.664  -1.232  1.00  0.00           C  
HETATM   29  C21 UNL     1       1.233  -0.123  -0.692  1.00  0.00           C  
HETATM   30  C22 UNL     1      -0.265  -0.184  -0.707  1.00  0.00           C  
HETATM   31  O4  UNL     1      -0.822   0.702  -1.596  1.00  0.00           O  
HETATM   32  C23 UNL     1      -1.630   0.119  -2.550  1.00  0.00           C  
HETATM   33  H1  UNL     1      -5.071   1.944  -1.794  1.00  0.00           H  
HETATM   34  H2  UNL     1      -6.547   1.032  -1.230  1.00  0.00           H  
HETATM   35  H3  UNL     1      -5.975   2.548  -0.402  1.00  0.00           H  
HETATM   36  H4  UNL     1      -7.331   0.388   0.517  1.00  0.00           H  
HETATM   37  H5  UNL     1      -9.006  -0.911   3.233  1.00  0.00           H  
HETATM   38  H6  UNL     1      -9.152  -1.626   1.609  1.00  0.00           H  
HETATM   39  H7  UNL     1      -4.232  -2.163   3.272  1.00  0.00           H  
HETATM   40  H8  UNL     1      -2.710   0.814  -0.015  1.00  0.00           H  
HETATM   41  H9  UNL     1      -0.483  -0.610   1.406  1.00  0.00           H  
HETATM   42  H10 UNL     1      -1.047   2.181   1.261  1.00  0.00           H  
HETATM   43  H11 UNL     1       0.427   1.379   1.955  1.00  0.00           H  
HETATM   44  H12 UNL     1       0.152   2.550  -0.862  1.00  0.00           H  
HETATM   45  H13 UNL     1       1.185   2.921   0.497  1.00  0.00           H  
HETATM   46  H14 UNL     1       2.449   2.839  -1.462  1.00  0.00           H  
HETATM   47  H15 UNL     1       2.031   1.443  -2.437  1.00  0.00           H  
HETATM   48  H16 UNL     1       4.252   1.783  -2.601  1.00  0.00           H  
HETATM   49  H17 UNL     1       4.609   1.728  -0.824  1.00  0.00           H  
HETATM   50  H18 UNL     1       3.752  -0.731  -0.929  1.00  0.00           H  
HETATM   51  H19 UNL     1       3.653  -0.540  -2.716  1.00  0.00           H  
HETATM   52  H20 UNL     1       5.138   0.207   0.668  1.00  0.00           H  
HETATM   53  H21 UNL     1       6.889   0.407   2.284  1.00  0.00           H  
HETATM   54  H22 UNL     1       9.800  -0.791  -0.540  1.00  0.00           H  
HETATM   55  H23 UNL     1       8.024  -0.973  -2.246  1.00  0.00           H  
HETATM   56  H24 UNL     1       1.634  -0.828   0.102  1.00  0.00           H  
HETATM   57  H25 UNL     1       1.603  -0.447  -1.701  1.00  0.00           H  
HETATM   58  H26 UNL     1      -0.597  -1.247  -0.982  1.00  0.00           H  
HETATM   59  H27 UNL     1      -2.014   0.946  -3.201  1.00  0.00           H  
HETATM   60  H28 UNL     1      -2.485  -0.430  -2.114  1.00  0.00           H  
HETATM   61  H29 UNL     1      -1.037  -0.545  -3.209  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   36
CONECT    5    6    7    7
CONECT    6   37   38
CONECT    7    8    9
CONECT    9   10   10   39
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   40
CONECT   14   15   30   41
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   29
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22
CONECT   22   23   23   28
CONECT   23   24   52
CONECT   24   25   25   53
CONECT   25   26   27
CONECT   27   28   28   54
CONECT   28   55
CONECT   29   30   56   57
CONECT   30   31   58
CONECT   31   32
CONECT   32   59   60   61
END
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SMILES for HMDB0014742 (Cisapride)

CO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC
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INCHI for HMDB0014742 (Cisapride)

InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1
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Synonyms
ValueSource
(+-)-CisaprideChEBI
4-Amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamideChEBI
4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamideChEBI
cis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-O-anisamideChEBI
cis-4-Amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamideChEBI
cis-4-Amino-5-chloro-N-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-O-anisamideChEBI
CisapridaChEBI
CisapridumChEBI
PropulsidHMDB
Chemical FormulaC23H29ClFN3O4
Average Molecular Weight465.945
Monoisotopic Molecular Weight465.183062343
IUPAC Name4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
Traditional Name(+-)-cisapride
CAS Registry Number81098-60-4
SMILES
CO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC
InChI Identifier
InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1
InChI KeyDCSUBABJRXZOMT-IRLDBZIGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzamides
Alternative Parents
Substituents
  • Aminobenzamide
  • Halobenzoic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • Aminophenyl ether
  • Methoxyaniline
  • Benzamide
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Aniline or substituted anilines
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl fluoride
  • Aryl halide
  • Piperidine
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Carboxamide group
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organofluoride
  • Organopnictogen compound
  • Organic oxide
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point110 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP3.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP2.95ALOGPS
logP2.49ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)8.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.05 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity122.93 m³·mol⁻¹ChemAxon
Polarizability49.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+204.5530932474
DeepCCS[M-H]-202.19230932474
DeepCCS[M-2H]-235.08830932474
DeepCCS[M+Na]+210.64430932474
AllCCS[M+H]+208.932859911
AllCCS[M+H-H2O]+206.932859911
AllCCS[M+NH4]+210.732859911
AllCCS[M+Na]+211.232859911
AllCCS[M-H]-203.332859911
AllCCS[M+Na-2H]-204.332859911
AllCCS[M+HCOO]-205.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CisaprideCO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC4809.0Standard polar33892256
CisaprideCO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC3864.1Standard non polar33892256
CisaprideCO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC3835.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cisapride,1TMS,isomer #1COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC3830.1Semi standard non polar33892256
Cisapride,1TMS,isomer #1COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC3389.2Standard non polar33892256
Cisapride,1TMS,isomer #1COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC4660.8Standard polar33892256
Cisapride,1TMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C3612.0Semi standard non polar33892256
Cisapride,1TMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C3312.2Standard non polar33892256
Cisapride,1TMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C4933.3Standard polar33892256
Cisapride,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC3670.1Semi standard non polar33892256
Cisapride,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC3358.0Standard non polar33892256
Cisapride,2TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC4417.8Standard polar33892256
Cisapride,2TMS,isomer #2COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C3696.5Semi standard non polar33892256
Cisapride,2TMS,isomer #2COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C3334.5Standard non polar33892256
Cisapride,2TMS,isomer #2COC1=CC(N[Si](C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C4380.2Standard polar33892256
Cisapride,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C3576.3Semi standard non polar33892256
Cisapride,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C3250.5Standard non polar33892256
Cisapride,3TMS,isomer #1COC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C4109.0Standard polar33892256
Cisapride,1TBDMS,isomer #1COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC4014.2Semi standard non polar33892256
Cisapride,1TBDMS,isomer #1COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC3592.3Standard non polar33892256
Cisapride,1TBDMS,isomer #1COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC4698.1Standard polar33892256
Cisapride,1TBDMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C3805.0Semi standard non polar33892256
Cisapride,1TBDMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C3517.0Standard non polar33892256
Cisapride,1TBDMS,isomer #2COC1=CC(N)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C4905.2Standard polar33892256
Cisapride,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC4101.4Semi standard non polar33892256
Cisapride,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC3768.1Standard non polar33892256
Cisapride,2TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N[C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC4464.3Standard polar33892256
Cisapride,2TBDMS,isomer #2COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C4039.9Semi standard non polar33892256
Cisapride,2TBDMS,isomer #2COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C3696.4Standard non polar33892256
Cisapride,2TBDMS,isomer #2COC1=CC(N[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C4463.5Standard polar33892256
Cisapride,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C4155.2Semi standard non polar33892256
Cisapride,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C3833.8Standard non polar33892256
Cisapride,3TBDMS,isomer #1COC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C1C(=O)N([C@@H]1CCN(CCCOC2=CC=C(F)C=C2)C[C@@H]1OC)[Si](C)(C)C(C)(C)C4220.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cisapride GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2922000000-0772f474daac82b426ee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cisapride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cisapride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cisapride LC-ESI-qTof , Positive-QTOFsplash10-001i-0980000000-a0df861122e90da3494b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cisapride , positive-QTOFsplash10-001i-0980000000-a0df861122e90da3494b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cisapride , positive-QTOFsplash10-0159-0710900000-262b97df953edaab4cfa2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 10V, Positive-QTOFsplash10-0159-0111900000-61265dea2a01bd8e83782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 20V, Positive-QTOFsplash10-001i-0943300000-cdcfabdf19797140d7952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 40V, Positive-QTOFsplash10-0006-9861100000-46b94051a1f1227c93632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 10V, Negative-QTOFsplash10-03di-0400900000-c6cda5b55f88160e99de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 20V, Negative-QTOFsplash10-03di-0921500000-6011948830548e90b8dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 40V, Negative-QTOFsplash10-03di-2910000000-5144f15cb7a70d64b8a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 10V, Positive-QTOFsplash10-014i-0001900000-8df7d19bd80f8e92fe732021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 20V, Positive-QTOFsplash10-0gb9-0439600000-d40cbd486ff327890e072021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 40V, Positive-QTOFsplash10-03ea-4902100000-c20a14020bf3f34d23dd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 10V, Negative-QTOFsplash10-03di-0100900000-10eb08fa13f12fb9bc9d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 20V, Negative-QTOFsplash10-03di-5915600000-de23551ac41099e763f92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cisapride 40V, Negative-QTOFsplash10-0il0-9411000000-a20e7213ffcaf2d0f91f2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00604 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00604 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00604
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5292927
KEGG Compound IDC06910
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCisapride
METLIN IDNot Available
PubChem Compound6917698
PDB IDNot Available
ChEBI ID3720
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pearce RE, Gotschall RR, Kearns GL, Leeder JS: Cytochrome P450 Involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos. 2001 Dec;29(12):1548-54. [PubMed:11717173 ]

Only showing the first 10 proteins. There are 14 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
  1. 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 ]
  2. Pearce RE, Gotschall RR, Kearns GL, Leeder JS: Cytochrome P450 Involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos. 2001 Dec;29(12):1548-54. [PubMed:11717173 ]
Enzyme Details
2. Cytochrome P450 2C9
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. 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 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
  1. 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
  1. 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 2B6
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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. 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
6. 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
References
  1. 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
7. 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
References
  1. 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. 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
  1. 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
9. Cytochrome P450 2C8
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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. 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
10. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. 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 ]

Only showing the first 10 proteins. There are 14 proteins in total.

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