NP-MRD: Showing NP-Card for Metoclopramide (NP0002916)

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Record Information

Version

1.0

Created at

2020-11-23 19:43:33 UTC

Updated at

2021-08-12 19:52:30 UTC

NP-MRD ID

NP0002916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Metoclopramide

Provided By

BMRB

Description

Metoclopramide, also known as elieten or reliveran, belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on Metoclopramide (PMID: 34346598) (PMID: 34337829) (PMID: 34316385) (PMID: 34296251).

Structure

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


     RDKit          2D

 42 42  0  0  0  0  0  0  0  0999 V2000
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    5.0611   -1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -2.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -0.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1075   -0.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3472   -1.1080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916   -0.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814    1.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2564   -1.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1212   -3.6494    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.7554   -1.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8906    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4804    2.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5249    3.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
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 16 37  1  0
 16 38  1  0
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 20 42  1  0
M  END

NP0002916
     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    5.3850    1.3652   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    0.9102    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    0.0786   -0.3786 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418   -1.2186   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -2.0823    0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -0.0808   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    1.2064   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    1.0090    0.0009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.0924   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -0.5510   -1.6881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -0.2003   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863   -1.1710   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1037   -2.7017   -2.2205 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0518   -0.8848   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4871    0.0574    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6204    1.3596    1.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4415    1.9474    2.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.6305    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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M  END


     RDKit          2D

 42 42  0  0  0  0  0  0  0  0999 V2000
    4.8371    2.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0167   -0.0095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0611   -1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -2.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -0.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3472   -1.1080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9814    1.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8906    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4804    2.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5249    3.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0
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  9 11  1  0
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 13 14  1  0
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 18 19  1  0
 19 20  1  0
 18 11  1  0
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  4 27  1  0
  5 28  1  1
  5 29  1  0
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  6 31  1  6
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M  END
> <DATABASE_ID>
NP0002916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)

> <INCHI_KEY>
TTWJBBZEZQICBI-UHFFFAOYSA-N

> <FORMULA>
C14H22ClN3O2

> <MOLECULAR_WEIGHT>
299.796

> <EXACT_MASS>
299.14005467

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.700490906362454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
1.3972700643333331

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.77630126903981

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.490737398855252

> <JCHEM_PKA_STRONGEST_BASIC>
9.04434504788954

> <JCHEM_POLAR_SURFACE_AREA>
67.59

> <JCHEM_REFRACTIVITY>
83.5178

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
metoclopramide

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002916
     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    5.3850    1.3652   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    0.9102    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    0.0786   -0.3786 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418   -1.2186   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -2.0823    0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -0.0808   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    1.2064   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    1.0090    0.0009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.0924   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -0.5510   -1.6881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -0.2003   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863   -1.1710   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986   -1.5005   -1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1037   -2.7017   -2.2205 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0518   -0.8848   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4355   -1.2512   -0.0860 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    0.0574    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1386    0.4096    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6204    1.3596    1.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4415    1.9474    2.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.6305    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557    2.3182    0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686    1.5449   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4922    1.8391    0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2130    0.4409    1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -1.0794   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395   -1.7408   -1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8759   -2.5835    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1804   -2.9331    0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5469   -1.4833    1.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.3986    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5230   -0.9380   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965    2.0371    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    1.5021   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118    1.5827    0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -1.6656   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1481   -0.4984    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7132   -2.2522   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597    0.5515    1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    2.7105    2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8667    1.1676    2.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789    2.4543    1.7451 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  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 12 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1233                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       9.748  -4.766   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.414  -1.686   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748   0.624   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.748   4.474   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.415   0.624   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081  -6.306   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748   2.934   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   5.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   5.244   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   2.164   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   6.784   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   6.784   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -0.146   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -1.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -2.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -2.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -3.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -4.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -3.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -2.456   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   15   20                                                       
CONECT    3   13                                                            
CONECT    4    7    8    9                                                  
CONECT    5   10   13                                                       
CONECT    6   18                                                            
CONECT    7    4   10                                                       
CONECT    8    4   11                                                       
CONECT    9    4   12                                                       
CONECT   10    5    7                                                       
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    3    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15    2   14   17                                                  
CONECT   16   14   19                                                       
CONECT   17   15   18                                                       
CONECT   18    6   17   19                                                  
CONECT   19    1   16   18                                                  
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    NP0002916
HETATM    1  C1  UNL     1       5.385   1.365  -0.070  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.057   0.910   0.501  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.323   0.079  -0.379  1.00  0.00           N  
HETATM    4  C3  UNL     1       3.942  -1.219  -0.598  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.913  -2.082   0.640  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.928  -0.081  -0.068  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.201   1.206  -0.312  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.248   1.009   0.001  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.999   0.092  -0.732  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.390  -0.551  -1.688  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.391  -0.200  -0.517  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.986  -1.171  -1.361  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.299  -1.501  -1.210  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -5.104  -2.702  -2.220  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -5.052  -0.885  -0.229  1.00  0.00           C  
HETATM   16  N3  UNL     1      -6.435  -1.251  -0.086  1.00  0.00           N  
HETATM   17  C12 UNL     1      -4.487   0.057   0.596  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.139   0.410   0.455  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.620   1.360   1.306  1.00  0.00           O  
HETATM   20  C14 UNL     1      -3.442   1.947   2.282  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.202   0.630   0.173  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.656   2.318   0.411  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.269   1.545  -1.149  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.492   1.839   0.696  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.213   0.441   1.507  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.943  -1.079  -1.001  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.339  -1.741  -1.371  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.876  -2.584   0.839  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.180  -2.933   0.539  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.547  -1.483   1.510  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.800  -0.399   1.017  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.523  -0.938  -0.636  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.597   2.037   0.270  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.196   1.502  -1.376  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.612   1.583   0.765  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.405  -1.666  -2.140  1.00  0.00           H  
HETATM   37  H17 UNL     1      -7.148  -0.498   0.083  1.00  0.00           H  
HETATM   38  H18 UNL     1      -6.713  -2.252  -0.153  1.00  0.00           H  
HETATM   39  H19 UNL     1      -5.060   0.552   1.368  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.906   2.711   2.880  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.867   1.168   2.966  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.279   2.454   1.745  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    6
CONECT    4    5   26   27
CONECT    5   28   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   36
CONECT   13   14   15   15
CONECT   15   16   17
CONECT   16   37   38
CONECT   17   18   18   39
CONECT   18   19
CONECT   19   20
CONECT   20   40   41   42
END

NP0002916
     RDKit          3D

42 42  0  0  0  0  0  0  0  0999 V2000
    5.3850    1.3652   -0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0572    0.9102    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    0.0786   -0.3786 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9418   -1.2186   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126   -2.0823    0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285   -0.0808   -0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008    1.2064   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    1.0090    0.0009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.0924   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899   -0.5510   -1.6881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -0.2003   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863   -1.1710   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986   -1.5005   -1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1037   -2.7017   -2.2205 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0518   -0.8848   -0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4355   -1.2512   -0.0860 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4871    0.0574    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1386    0.4096    0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6204    1.3596    1.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4415    1.9474    2.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2022    0.6305    0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557    2.3182    0.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686    1.5449   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4922    1.8391    0.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2130    0.4409    1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -1.0794   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3395   -1.7408   -1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8759   -2.5835    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1804   -2.9331    0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5469   -1.4833    1.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.3986    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5230   -0.9380   -0.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965    2.0371    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    1.5021   -1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118    1.5827    0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -1.6656   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1481   -0.4984    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7132   -2.2522   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597    0.5515    1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    2.7105    2.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8667    1.1676    2.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2789    2.4543    1.7451 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  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
 12 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-Methoxy-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide	ChEBI
2-Methoxy-5-chloroprocainamide	ChEBI
4-Amino-5-chloro-2-methoxy-N-(beta-diethylaminoethyl)benzamide	ChEBI
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide	ChEBI
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-O-anisamide	ChEBI
Elieten	ChEBI
Metoclopramida	ChEBI
Metoclopramidum	ChEBI
Reliveran	ChEBI
Terperan	Kegg
4-Amino-5-chloro-2-methoxy-N-(b-diethylaminoethyl)benzamide	Generator
4-Amino-5-chloro-2-methoxy-N-(β-diethylaminoethyl)benzamide	Generator
Metaclopramide	HMDB
Metaclopromide	HMDB
Methochlopramide	HMDB
Methoclopramide	HMDB
Metochlopramide	HMDB
Berk brand OF metoclopramide hydrochloride	HMDB
Dihydrochloride, metoclopramide	HMDB
Maxolon	HMDB
Primperan	HMDB
Cerucal	HMDB
Temmler brand OF metoclopramide hydrochloride	HMDB
Hydrochloride, metoclopramide	HMDB
Monohydrochloride, metoclopramide	HMDB
Rimetin	HMDB
Metoclopramide dihydrochloride	HMDB
Metoclopramide hydrochloride	HMDB
Metoclopramide monohydrochloride	HMDB
Metoclopramide monohydrochloride, monohydrate	HMDB
Reglan	HMDB

Chemical Formula

C₁₄H₂₂ClN₃O₂

Average Mass

299.7960 Da

Monoisotopic Mass

299.14005 Da

IUPAC Name

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide

Traditional Name

metoclopramide

CAS Registry Number

Not Available

SMILES

CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC

InChI Identifier

InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)

InChI Key

TTWJBBZEZQICBI-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Aminophenyl ethers

Direct Parent

Aminophenyl ethers

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.18	ALOGPS
logP	1.4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.49	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	83.52 m³·mol⁻¹	ChemAxon
Polarizability	32.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015363

DrugBank ID

DB01233

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4024

KEGG Compound ID

C07868

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Metoclopramide

METLIN ID

Not Available

PubChem Compound

4168

PDB ID

Not Available

ChEBI ID

107736

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
van Dooijeweert B, Verschuur AVD, Visser NA, Jansen J: [A toddler with status dystonicus due to medication]. Ned Tijdschr Geneeskd. 2021 Jun 8;165. [PubMed:34346598 ]
Cheng I, Sasegbon A, Hamdy S: Effects of pharmacological agents for neurogenic oropharyngeal dysphagia: A systematic review and meta-analysis. Neurogastroenterol Motil. 2021 Aug 1:e14220. doi: 10.1111/nmo.14220. [PubMed:34337829 ]
Takashima K, Komeda Y, Sakurai T, Masaki S, Nagai T, Matsui S, Hagiwara S, Takenaka M, Nishida N, Kashida H, Nakaji K, Watanabe T, Kudo M: Castor oil as booster for colon capsule endoscopy preparation reduction: A prospective pilot study and patient questionnaire. World J Gastrointest Pharmacol Ther. 2021 Jul 5;12(4):79-89. doi: 10.4292/wjgpt.v12.i4.79. [PubMed:34316385 ]
Farid NF, Abdelhamid NS, Naguib IA, Anwar BH, Magdy MA: Quantitative Determination of Anti-Migraine Quaternary Mixture in Presence of p-Aminophenol and 4-Chloroacetanilide. J Chromatogr Sci. 2021 Jul 23. pii: 6326037. doi: 10.1093/chromsci/bmab093. [PubMed:34296251 ]

Showing NP-Card for Metoclopramide (NP0002916)

MOL for NP0002916 (Metoclopramide)

3D MOL for NP0002916 (Metoclopramide)

3D SDF for NP0002916 (Metoclopramide)

3D-SDF for NP0002916 (Metoclopramide)

PDB for NP0002916 (Metoclopramide)

3D PDB for NP0002916 (Metoclopramide)

SMILES for NP0002916 (Metoclopramide)

INCHI for NP0002916 (Metoclopramide)

Structure for NP0002916 (Metoclopramide)

3D Structure for NP0002916 (Metoclopramide)