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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015698

Secondary Accession Numbers

HMDB15698

Metabolite Identification

Common Name

Cinitapride

Description

Cinitapride, also known as paxapride or blaston, belongs to the class of organic compounds known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring. Cinitapride is a gastroprokinetic agent and antiulcer agent of the benzamide class which is marketed in Spain and Mexico. Cinitapride is only found in individuals that have used or taken this drug. Cinitapride is a very strong basic compound (based on its pKa). Cinitapride is a gastroprokinetic agent and antiulcer benzamide with agonist activity at 5-HT1 and 5-HT4 receptors and antagonist activity at 5-HT2 receptors. It acts as an agonist of the 5-HT1 and 5-HT4 receptors and as an antagonist of the 5-HT2 receptors. It is marketed in Spain and Mexico.

Structure

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

68867
  Mrv0541 02241214212D          

 29 31  0  0  1  0            999 V2000
    3.7935   -0.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9659    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.3784    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2 23  1  0  0  0  0
  2 28  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  2  0  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 11  1  0  0  0  0
  6 21  1  0  0  0  0
  7 25  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 11 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 26  2  0  0  0  0
 24 25  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  2   3  -1   7   1
M  END

HMDB0015698
     RDKit          3D
Cinitapride
 59 61  0  0  0  0  0  0  0  0999 V2000
   -3.8530    0.9737   -2.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555    1.6803   -2.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100    1.1059   -0.7788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8425    1.0031    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0832    1.5327   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1670    1.4726    0.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4398    2.0178    0.1714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9995    0.8780    1.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1142    0.7956    2.6914 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.9473    0.7449    3.9318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3752    0.7701    2.1978 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.7895    0.3666    2.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.4018    1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -0.1582    1.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -0.6809    2.9684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -0.1944    1.0681 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0222   -0.7847    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098   -2.0117    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -1.5635   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547   -1.3953    0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221   -0.5841   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352   -0.3234   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.6088   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3249   -2.0193   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9402   -1.1105   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8352    0.3028   -1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4056    0.6502   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4320   -0.7988    1.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1936    0.1193    1.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914    0.4769   -3.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424    0.1521   -2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5454    1.6620   -3.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8438    1.6314   -2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1255    2.7508   -2.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2309    2.0046   -1.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6161    3.0397    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2422    1.3836   -0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6550   -0.1068    3.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931    0.1971    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -1.1695    2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831   -2.3101    0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339   -2.8755    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239   -0.6437   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -2.3114   -1.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.3856   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -1.1047   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    0.1833    0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2456   -1.6441    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8196   -2.4181    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -3.0843   -1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5024   -1.3362   -2.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5122    0.5199   -0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232    0.9523   -2.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4028    1.6922   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274    0.6376   -2.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478   -1.5412    2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769   -0.1245    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504    0.7755    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    0.6437    2.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 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  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 20 28  1  0
 28 29  1  0
 13  4  1  0
 29 17  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
M  CHG  2   9   1  11  -1
M  END

68867
  Mrv0541 02241214212D          

 29 31  0  0  1  0            999 V2000
    3.7935   -0.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.9659    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.9370   -4.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.3784    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5080   -4.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    4.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  2  0  0  0  0
  2 23  1  0  0  0  0
  2 28  1  0  0  0  0
  3  7  1  0  0  0  0
  4  7  2  0  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 11  1  0  0  0  0
  6 21  1  0  0  0  0
  7 25  1  0  0  0  0
  8 27  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
  9 17  1  0  0  0  0
 11 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 18  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 26  2  0  0  0  0
 24 25  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  2   3  -1   7   1
M  END
> <DATABASE_ID>
HMDB0015698

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)

> <INCHI_KEY>
ZDLBNXXKDMLZMF-UHFFFAOYSA-N

> <FORMULA>
C21H30N4O4

> <MOLECULAR_WEIGHT>
402.4873

> <EXACT_MASS>
402.226705468

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
44.294356016084805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
2.786924839

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.31941348656527

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.891745056418646

> <JCHEM_PKA_STRONGEST_BASIC>
9.744756100760855

> <JCHEM_POLAR_SURFACE_AREA>
113.41000000000001

> <JCHEM_REFRACTIVITY>
115.58269999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinitapride

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015698
     RDKit          3D
Cinitapride
 59 61  0  0  0  0  0  0  0  0999 V2000
   -3.8530    0.9737   -2.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555    1.6803   -2.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100    1.1059   -0.7788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8425    1.0031    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0832    1.5327   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1670    1.4726    0.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4398    2.0178    0.1714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9995    0.8780    1.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1142    0.7956    2.6914 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.9473    0.7449    3.9318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3752    0.7701    2.1978 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.7895    0.3666    2.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.4018    1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -0.1582    1.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -0.6809    2.9684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -0.1944    1.0681 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0222   -0.7847    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098   -2.0117    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -1.5635   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547   -1.3953    0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221   -0.5841   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352   -0.3234   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.6088   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3249   -2.0193   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9402   -1.1105   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8352    0.3028   -1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4056    0.6502   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4320   -0.7988    1.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1936    0.1193    1.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914    0.4769   -3.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424    0.1521   -2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5454    1.6620   -3.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8438    1.6314   -2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1255    2.7508   -2.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2309    2.0046   -1.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6161    3.0397    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2422    1.3836   -0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6550   -0.1068    3.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931    0.1971    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -1.1695    2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831   -2.3101    0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339   -2.8755    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239   -0.6437   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -2.3114   -1.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.3856   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -1.1047   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    0.1833    0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2456   -1.6441    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8196   -2.4181    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -3.0843   -1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5024   -1.3362   -2.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5122    0.5199   -0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232    0.9523   -2.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4028    1.6922   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274    0.6376   -2.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478   -1.5412    2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769   -0.1245    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504    0.7755    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    0.6437    2.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 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  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 20 28  1  0
 28 29  1  0
 13  4  1  0
 29 17  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
M  CHG  2   9   1  11  -1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 68867                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081  -0.916   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748  -3.226   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.416  -5.536   0.000  0.00  0.00           O-1
HETATM    4  O   UNK     0      11.082  -7.847   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.748   3.704   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748  -0.916   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.082  -6.306   0.000  0.00  0.00           N+1
HETATM    8  N   UNK     0       8.415  -7.847   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      11.082   6.014   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   5.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   0.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   2.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082   2.934   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   1.394   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082   1.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   7.554   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   5.244   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416   8.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750   6.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.750   7.554   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -1.686   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -3.226   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -3.996   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.748  -3.996   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.748  -5.536   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.081  -5.536   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.415  -6.306   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414  -3.996   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080  -3.226   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   23   28                                                       
CONECT    3    7                                                            
CONECT    4    7                                                            
CONECT    5   10   12   13                                                  
CONECT    6   11   21                                                       
CONECT    7    3    4   25                                                  
CONECT    8   27                                                            
CONECT    9   10   16   17                                                  
CONECT   10    5    9                                                       
CONECT   11    6   14   15                                                  
CONECT   12    5   14                                                       
CONECT   13    5   15                                                       
CONECT   14   11   12                                                       
CONECT   15   11   13                                                       
CONECT   16    9   18                                                       
CONECT   17    9   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19                                                       
CONECT   21    1    6   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23    2   22   26                                                  
CONECT   24   22   25                                                       
CONECT   25    7   24   27                                                  
CONECT   26   23   27                                                       
CONECT   27    8   25   26                                                  
CONECT   28    2   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0015698
HETATM    1  C1  UNL     1      -3.853   0.974  -2.964  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.855   1.680  -2.053  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.810   1.106  -0.779  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.843   1.003   0.120  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.083   1.533  -0.263  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.167   1.473   0.572  1.00  0.00           C  
HETATM    7  N1  UNL     1      -7.440   2.018   0.171  1.00  0.00           N  
HETATM    8  C6  UNL     1      -6.000   0.878   1.795  1.00  0.00           C  
HETATM    9  N2  UNL     1      -7.114   0.796   2.691  1.00  0.00           N1+
HETATM   10  O2  UNL     1      -6.947   0.745   3.932  1.00  0.00           O  
HETATM   11  O3  UNL     1      -8.375   0.770   2.198  1.00  0.00           O1-
HETATM   12  C7  UNL     1      -4.789   0.367   2.159  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.645   0.402   1.339  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.397  -0.158   1.776  1.00  0.00           C  
HETATM   15  O4  UNL     1      -2.428  -0.681   2.968  1.00  0.00           O  
HETATM   16  N3  UNL     1      -1.196  -0.194   1.068  1.00  0.00           N  
HETATM   17  C10 UNL     1       0.022  -0.785   1.584  1.00  0.00           C  
HETATM   18  C11 UNL     1       0.310  -2.012   0.719  1.00  0.00           C  
HETATM   19  C12 UNL     1       1.350  -1.563  -0.282  1.00  0.00           C  
HETATM   20  N4  UNL     1       2.655  -1.395   0.398  1.00  0.00           N  
HETATM   21  C13 UNL     1       3.422  -0.584  -0.495  1.00  0.00           C  
HETATM   22  C14 UNL     1       4.835  -0.323  -0.110  1.00  0.00           C  
HETATM   23  C15 UNL     1       5.585  -1.609  -0.005  1.00  0.00           C  
HETATM   24  C16 UNL     1       6.325  -2.019  -1.207  1.00  0.00           C  
HETATM   25  C17 UNL     1       6.940  -1.111  -1.941  1.00  0.00           C  
HETATM   26  C18 UNL     1       6.835   0.303  -1.483  1.00  0.00           C  
HETATM   27  C19 UNL     1       5.406   0.650  -1.122  1.00  0.00           C  
HETATM   28  C20 UNL     1       2.432  -0.799   1.706  1.00  0.00           C  
HETATM   29  C21 UNL     1       1.194   0.119   1.678  1.00  0.00           C  
HETATM   30  H1  UNL     1      -3.291   0.477  -3.812  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.342   0.152  -2.426  1.00  0.00           H  
HETATM   32  H3  UNL     1      -4.545   1.662  -3.465  1.00  0.00           H  
HETATM   33  H4  UNL     1      -1.844   1.631  -2.540  1.00  0.00           H  
HETATM   34  H5  UNL     1      -3.125   2.751  -2.058  1.00  0.00           H  
HETATM   35  H6  UNL     1      -5.231   2.005  -1.212  1.00  0.00           H  
HETATM   36  H7  UNL     1      -7.616   3.040   0.091  1.00  0.00           H  
HETATM   37  H8  UNL     1      -8.242   1.384  -0.055  1.00  0.00           H  
HETATM   38  H9  UNL     1      -4.655  -0.107   3.134  1.00  0.00           H  
HETATM   39  H10 UNL     1      -1.093   0.197   0.127  1.00  0.00           H  
HETATM   40  H11 UNL     1      -0.207  -1.170   2.597  1.00  0.00           H  
HETATM   41  H12 UNL     1      -0.583  -2.310   0.134  1.00  0.00           H  
HETATM   42  H13 UNL     1       0.634  -2.875   1.309  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.024  -0.644  -0.772  1.00  0.00           H  
HETATM   44  H15 UNL     1       1.534  -2.311  -1.080  1.00  0.00           H  
HETATM   45  H16 UNL     1       2.888   0.386  -0.658  1.00  0.00           H  
HETATM   46  H17 UNL     1       3.431  -1.105  -1.478  1.00  0.00           H  
HETATM   47  H18 UNL     1       4.937   0.183   0.887  1.00  0.00           H  
HETATM   48  H19 UNL     1       6.246  -1.644   0.893  1.00  0.00           H  
HETATM   49  H20 UNL     1       4.820  -2.418   0.187  1.00  0.00           H  
HETATM   50  H21 UNL     1       6.372  -3.084  -1.506  1.00  0.00           H  
HETATM   51  H22 UNL     1       7.502  -1.336  -2.834  1.00  0.00           H  
HETATM   52  H23 UNL     1       7.512   0.520  -0.643  1.00  0.00           H  
HETATM   53  H24 UNL     1       7.123   0.952  -2.331  1.00  0.00           H  
HETATM   54  H25 UNL     1       5.403   1.692  -0.748  1.00  0.00           H  
HETATM   55  H26 UNL     1       4.827   0.638  -2.066  1.00  0.00           H  
HETATM   56  H27 UNL     1       2.348  -1.541   2.506  1.00  0.00           H  
HETATM   57  H28 UNL     1       3.277  -0.125   1.913  1.00  0.00           H  
HETATM   58  H29 UNL     1       1.350   0.775   0.813  1.00  0.00           H  
HETATM   59  H30 UNL     1       1.180   0.644   2.642  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   33   34
CONECT    3    4
CONECT    4    5    5   13
CONECT    5    6   35
CONECT    6    7    8    8
CONECT    7   36   37
CONECT    8    9   12
CONECT    9   10   10   11
CONECT   12   13   13   38
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   39
CONECT   17   18   29   40
CONECT   18   19   41   42
CONECT   19   20   43   44
CONECT   20   21   28
CONECT   21   22   45   46
CONECT   22   23   27   47
CONECT   23   24   48   49
CONECT   24   25   25   50
CONECT   25   26   51
CONECT   26   27   52   53
CONECT   27   54   55
CONECT   28   29   56   57
CONECT   29   58   59
END

HMDB0015698
     RDKit          3D
Cinitapride
 59 61  0  0  0  0  0  0  0  0999 V2000
   -3.8530    0.9737   -2.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555    1.6803   -2.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100    1.1059   -0.7788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8425    1.0031    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0832    1.5327   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1670    1.4726    0.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4398    2.0178    0.1714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9995    0.8780    1.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1142    0.7956    2.6914 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.9473    0.7449    3.9318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3752    0.7701    2.1978 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.7895    0.3666    2.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6447    0.4018    1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3968   -0.1582    1.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4280   -0.6809    2.9684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -0.1944    1.0681 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0222   -0.7847    1.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098   -2.0117    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -1.5635   -0.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6547   -1.3953    0.3975 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4221   -0.5841   -0.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8352   -0.3234   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5852   -1.6088   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3249   -2.0193   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9402   -1.1105   -1.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8352    0.3028   -1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4056    0.6502   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4320   -0.7988    1.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1936    0.1193    1.6784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2914    0.4769   -3.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3424    0.1521   -2.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5454    1.6620   -3.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8438    1.6314   -2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1255    2.7508   -2.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2309    2.0046   -1.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6161    3.0397    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2422    1.3836   -0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6550   -0.1068    3.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0931    0.1971    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -1.1695    2.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831   -2.3101    0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6339   -2.8755    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0239   -0.6437   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -2.3114   -1.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.3856   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4310   -1.1047   -1.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371    0.1833    0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2456   -1.6441    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8196   -2.4181    0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -3.0843   -1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5024   -1.3362   -2.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5122    0.5199   -0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232    0.9523   -2.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4028    1.6922   -0.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8274    0.6376   -2.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478   -1.5412    2.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2769   -0.1245    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504    0.7755    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    0.6437    2.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 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  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 20 28  1  0
 28 29  1  0
 13  4  1  0
 29 17  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  5 35  1  0
  7 36  1  0
  7 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
M  CHG  2   9   1  11  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Paxapride	Kegg
Blaston	HMDB
Cidine	HMDB
Cinitapride tartrate	HMDB
4-Amino-N-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide	MeSH

Chemical Formula

C₂₁H₃₀N₄O₄

Average Molecular Weight

402.4873

Monoisotopic Molecular Weight

402.226705468

IUPAC Name

4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide

Traditional Name

cinitapride

CAS Registry Number

66564-14-5

SMILES

CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O

InChI Identifier

InChI=1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)

InChI Key

ZDLBNXXKDMLZMF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrophenyl ethers

Alternative Parents

Substituents

Nitrophenyl ether
Aminobenzamide
Aminobenzoic acid or derivatives
Aminophenyl ether
Benzamide
Benzoic acid or derivatives
Phenoxy compound
Nitroaromatic compound
Benzoyl
Phenol ether
Aniline or substituted anilines
Alkyl aryl ether
Piperidine
Amino acid or derivatives
Carboxamide group
C-nitro compound
Organic nitro compound
Secondary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Organic 1,3-dipolar compound
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Azacycle
Organic oxoazanium
Carboxylic acid derivative
Ether
Primary amine
Organic nitrogen compound
Amine
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organic zwitterion
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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: HMDB0015698)

Source

Exogenous

Exogenous (HMDB: HMDB0015698)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.7	ALOGPS
logP	2.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	9.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.41 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	115.58 m³·mol⁻¹	ChemAxon
Polarizability	44.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	194.419	31661259
DarkChem	[M-H]-	192.267	31661259
DeepCCS	[M+H]+	192.699	30932474
DeepCCS	[M-H]-	190.341	30932474
DeepCCS	[M-2H]-	223.227	30932474
DeepCCS	[M+Na]+	198.792	30932474
AllCCS	[M+H]+	196.7	32859911
AllCCS	[M+H-H2O]+	194.4	32859911
AllCCS	[M+NH4]+	198.7	32859911
AllCCS	[M+Na]+	199.3	32859911
AllCCS	[M-H]-	190.2	32859911
AllCCS	[M+Na-2H]-	190.8	32859911
AllCCS	[M+HCOO]-	191.6	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.	3.86 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8964 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.84 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	61.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1403.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	176.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	104.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	304.1 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	384.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	425.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	877.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	395.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1057.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	273.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	515.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	354.5 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	18.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinitapride	CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O	3629.5	Standard polar	33892256
Cinitapride	CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O	3371.6	Standard non polar	33892256
Cinitapride	CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O	3757.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cinitapride,1TMS,isomer #1	CCOC1=CC(N[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3559.4	Semi standard non polar	33892256
Cinitapride,1TMS,isomer #1	CCOC1=CC(N[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3247.6	Standard non polar	33892256
Cinitapride,1TMS,isomer #1	CCOC1=CC(N[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	4403.9	Standard polar	33892256
Cinitapride,1TMS,isomer #2	CCOC1=CC(N)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	3378.0	Semi standard non polar	33892256
Cinitapride,1TMS,isomer #2	CCOC1=CC(N)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	3249.6	Standard non polar	33892256
Cinitapride,1TMS,isomer #2	CCOC1=CC(N)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	4716.6	Standard polar	33892256
Cinitapride,2TMS,isomer #1	CCOC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3459.5	Semi standard non polar	33892256
Cinitapride,2TMS,isomer #1	CCOC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3310.3	Standard non polar	33892256
Cinitapride,2TMS,isomer #1	CCOC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	4227.9	Standard polar	33892256
Cinitapride,2TMS,isomer #2	CCOC1=CC(N[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	3467.3	Semi standard non polar	33892256
Cinitapride,2TMS,isomer #2	CCOC1=CC(N[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	3314.5	Standard non polar	33892256
Cinitapride,2TMS,isomer #2	CCOC1=CC(N[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	4266.8	Standard polar	33892256
Cinitapride,3TMS,isomer #1	CCOC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	3404.8	Semi standard non polar	33892256
Cinitapride,3TMS,isomer #1	CCOC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	3381.3	Standard non polar	33892256
Cinitapride,3TMS,isomer #1	CCOC1=CC(N([Si](C)(C)C)[Si](C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C	4026.3	Standard polar	33892256
Cinitapride,1TBDMS,isomer #1	CCOC1=CC(N[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3722.7	Semi standard non polar	33892256
Cinitapride,1TBDMS,isomer #1	CCOC1=CC(N[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3463.5	Standard non polar	33892256
Cinitapride,1TBDMS,isomer #1	CCOC1=CC(N[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	4464.7	Standard polar	33892256
Cinitapride,1TBDMS,isomer #2	CCOC1=CC(N)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	3588.4	Semi standard non polar	33892256
Cinitapride,1TBDMS,isomer #2	CCOC1=CC(N)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	3456.0	Standard non polar	33892256
Cinitapride,1TBDMS,isomer #2	CCOC1=CC(N)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	4754.6	Standard polar	33892256
Cinitapride,2TBDMS,isomer #1	CCOC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3846.4	Semi standard non polar	33892256
Cinitapride,2TBDMS,isomer #1	CCOC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	3670.8	Standard non polar	33892256
Cinitapride,2TBDMS,isomer #1	CCOC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1	4266.5	Standard polar	33892256
Cinitapride,2TBDMS,isomer #2	CCOC1=CC(N[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	3838.3	Semi standard non polar	33892256
Cinitapride,2TBDMS,isomer #2	CCOC1=CC(N[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	3704.3	Standard non polar	33892256
Cinitapride,2TBDMS,isomer #2	CCOC1=CC(N[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	4329.1	Standard polar	33892256
Cinitapride,3TBDMS,isomer #1	CCOC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	3948.9	Semi standard non polar	33892256
Cinitapride,3TBDMS,isomer #1	CCOC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	3902.5	Standard non polar	33892256
Cinitapride,3TBDMS,isomer #1	CCOC1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C([N+](=O)[O-])C=C1C(=O)N(C1CCN(CC2CC=CCC2)CC1)[Si](C)(C)C(C)(C)C	4080.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cinitapride GC-MS (Non-derivatized) - 70eV, Positive	splash10-009x-8579000000-39b68a617611dab9e95b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinitapride GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinitapride 10V, Positive-QTOF	splash10-0udi-0000900000-4b788ff2c08efd55308c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinitapride 20V, Positive-QTOF	splash10-0002-3109200000-6d689d0776cf6ede53b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinitapride 40V, Positive-QTOF	splash10-0002-9302000000-605bbfee5223e09ee316	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinitapride 10V, Negative-QTOF	splash10-0udi-1001900000-0470125164c5752027f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinitapride 20V, Negative-QTOF	splash10-0udi-3102900000-03c1a981392d4281690f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinitapride 40V, Negative-QTOF	splash10-000w-9401000000-7539a8f40c5246a8c9e0	2016-08-03	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 DB08810	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08810	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08810

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

62099

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cinitapride

METLIN ID

Not Available

PubChem Compound

68867

PDB ID

Not Available

ChEBI ID

Not Available

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

Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [PubMed:9211565 ]

Enzymes

Enzyme Details

1. 5-hydroxytryptamine receptor 4

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:: HTR4
Uniprot ID:: Q13639
Molecular weight:: 43761.0

References

Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [PubMed:9211565 ]
Alarcon de la Lastra C, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. [PubMed:9562338 ]

Enzyme Details

2. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [PubMed:9211565 ]
Alarcon de la Lastra C, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. [PubMed:9562338 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [PubMed:9211565 ]
Alarcon de la Lastra C, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. [PubMed:9562338 ]

Showing metabocard for Cinitapride (HMDB0015698)

MOL for HMDB0015698 (Cinitapride)

3D MOL for HMDB0015698 (Cinitapride)

3D SDF for HMDB0015698 (Cinitapride)

3D-SDF for HMDB0015698 (Cinitapride)

PDB for HMDB0015698 (Cinitapride)

3D PDB for HMDB0015698 (Cinitapride)

SMILES for HMDB0015698 (Cinitapride)

INCHI for HMDB0015698 (Cinitapride)

Structure for HMDB0015698 (Cinitapride)

3D Structure for HMDB0015698 (Cinitapride)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References