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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015363

Secondary Accession Numbers

HMDB15363

Metabolite Identification

Common Name

Metoclopramide

Description

Metoclopramide is only found in individuals that have used or taken this drug. It is a dopamine D2 antagonist that is used as an antiemetic. [PubChem]Metoclopramide inhibits gastric smooth muscle relaxation produced by dopamine, therefore increasing cholinergic response of the gastrointestinal smooth muscle. It accelerates intestinal transit and gastric emptying by preventing relaxation of gastric body and increasing the phasic activity of antrum. Simultaneously, this action is accompanied by relaxation of the upper small intestine, resulting in an improved coordination between the body and antrum of the stomach and the upper small intestine. Metoclopramide also decreases reflux into the esophagus by increasing the resting pressure of the lower esophageal sphincter and improves acid clearance from the esophagus by increasing amplitude of esophageal peristaltic contractions. Metoclopramide's dopamine antagonist action raises the threshold of activity in the chemoreceptor trigger zone and decreases the input from afferent visceral nerves. Studies have also shown that high doses of metoclopramide can antagonize 5-hydroxytryptamine (5-HT) receptors in the peripheral nervous system in animals.

Structure

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

HMDB0015363
     RDKit          3D
Metoclopramide
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5833    2.5993    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    1.1773    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    0.1941    0.8551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1788   -0.0285    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -0.6106   -0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648   -0.8130    1.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5285   -1.8150    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.3826    0.3996 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -0.8726    1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4724   -0.8319    2.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0254   -0.3958    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    0.0689    1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355    0.5342    1.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500    1.1271    2.6907 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5827    0.5662    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799    1.0556   -0.1561 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516    0.1154   -0.8459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -0.3607   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -0.8139   -1.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637   -0.7950   -2.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138    3.3245    0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    2.6982    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    2.7894   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0301    1.1431    0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    1.0784   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6855    0.9678    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7767   -0.6523    1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152   -1.7420   -0.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1184   -0.2894   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2895   -0.2368   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976   -1.3728    2.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196   -0.3280    2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268   -2.3426    0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329   -2.6647    1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.4542   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5907    0.0690    2.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6488    0.4736   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    2.0794    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042    0.0967   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -1.0685   -3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    0.2181   -3.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827   -1.5051   -3.0728 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

1233
  Mrv0541 02231215202D          

 20 20  0  0  0  0            999 V2000
    5.2224   -2.5534    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.3967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.3784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 15  1  0  0  0  0
  2 20  1  0  0  0  0
  3 13  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6 18  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015363

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0015363
     RDKit          3D
Metoclopramide
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5833    2.5993    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    1.1773    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    0.1941    0.8551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1788   -0.0285    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -0.6106   -0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648   -0.8130    1.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5285   -1.8150    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.3826    0.3996 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -0.8726    1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4724   -0.8319    2.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0254   -0.3958    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    0.0689    1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355    0.5342    1.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500    1.1271    2.6907 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5827    0.5662    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799    1.0556   -0.1561 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516    0.1154   -0.8459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -0.3607   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -0.8139   -1.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637   -0.7950   -2.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138    3.3245    0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    2.6982    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    2.7894   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0301    1.1431    0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    1.0784   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6855    0.9678    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7767   -0.6523    1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152   -1.7420   -0.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1184   -0.2894   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2895   -0.2368   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976   -1.3728    2.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196   -0.3280    2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268   -2.3426    0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329   -2.6647    1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.4542   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5907    0.0690    2.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6488    0.4736   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    2.0794    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042    0.0967   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -1.0685   -3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    0.2181   -3.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827   -1.5051   -3.0728 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    HMDB0015363
HETATM    1  C1  UNL     1      -2.583   2.599   0.541  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.075   1.177   0.278  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.857   0.194   0.855  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.179  -0.029   0.395  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.167  -0.611  -0.988  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.365  -0.813   1.690  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.528  -1.815   0.986  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.302  -1.383   0.400  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.727  -0.873   1.222  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.472  -0.832   2.488  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.025  -0.396   0.795  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.888   0.069   1.802  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.136   0.534   1.454  1.00  0.00           C  
HETATM   14 CL1  UNL     1       5.250   1.127   2.691  1.00  0.00          CL  
HETATM   15  C11 UNL     1       4.583   0.566   0.151  1.00  0.00           C  
HETATM   16  N3  UNL     1       5.880   1.056  -0.156  1.00  0.00           N  
HETATM   17  C12 UNL     1       3.752   0.115  -0.846  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.479  -0.361  -0.503  1.00  0.00           C  
HETATM   19  O2  UNL     1       1.646  -0.814  -1.503  1.00  0.00           O  
HETATM   20  C14 UNL     1       2.064  -0.795  -2.851  1.00  0.00           C  
HETATM   21  H1  UNL     1      -1.814   3.324   0.181  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.718   2.698   1.621  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.504   2.789  -0.044  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.030   1.143   0.666  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.015   1.078  -0.820  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.685   0.968   0.336  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.777  -0.652   1.109  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.115  -1.742  -0.978  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.118  -0.289  -1.471  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.290  -0.237  -1.532  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.198  -1.373   2.229  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.820  -0.328   2.545  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.127  -2.343   0.181  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.333  -2.665   1.722  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.197  -1.454  -0.630  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.591   0.069   2.845  1.00  0.00           H  
HETATM   37  H17 UNL     1       6.649   0.474  -0.539  1.00  0.00           H  
HETATM   38  H18 UNL     1       6.104   2.079   0.005  1.00  0.00           H  
HETATM   39  H19 UNL     1       4.004   0.097  -1.891  1.00  0.00           H  
HETATM   40  H20 UNL     1       1.234  -1.068  -3.543  1.00  0.00           H  
HETATM   41  H21 UNL     1       2.430   0.218  -3.162  1.00  0.00           H  
HETATM   42  H22 UNL     1       2.883  -1.505  -3.073  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

HMDB0015363
     RDKit          3D
Metoclopramide
 42 42  0  0  0  0  0  0  0  0999 V2000
   -2.5833    2.5993    0.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    1.1773    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    0.1941    0.8551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1788   -0.0285    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1671   -0.6106   -0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648   -0.8130    1.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5285   -1.8150    0.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.3826    0.3996 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -0.8726    1.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4724   -0.8319    2.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0254   -0.3958    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8884    0.0689    1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1355    0.5342    1.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500    1.1271    2.6907 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5827    0.5662    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799    1.0556   -0.1561 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516    0.1154   -0.8459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -0.3607   -0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -0.8139   -1.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0637   -0.7950   -2.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8138    3.3245    0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    2.6982    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    2.7894   -0.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0301    1.1431    0.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145    1.0784   -0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6855    0.9678    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7767   -0.6523    1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152   -1.7420   -0.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1184   -0.2894   -1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2895   -0.2368   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1976   -1.3728    2.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196   -0.3280    2.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268   -2.3426    0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329   -2.6647    1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -1.4542   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5907    0.0690    2.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6488    0.4736   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042    2.0794    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042    0.0967   -1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -1.0685   -3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297    0.2181   -3.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827   -1.5051   -3.0728 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 View Stereo Labels

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 Molecular Weight

299.796

Monoisotopic Molecular Weight

299.14005467

IUPAC Name

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

Traditional Name

metoclopramide

CAS Registry Number

364-62-5

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

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

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Methoxybenzene
Aniline or substituted anilines
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Organic 1,3-dipolar compound
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Ether
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:107736 )
substituted aniline (CHEBI:107736 )
benzamides (CHEBI:107736 )
monochlorobenzenes (CHEBI:107736 )

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

Cytoplasm (HMDB: HMDB0015363)
Membrane (HMDB: HMDB0015363)

Source

Exogenous

Exogenous (HMDB: HMDB0015363)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147.25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.31 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	173.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	168.622	30932474
DeepCCS	[M-H]-	166.264	30932474
DeepCCS	[M-2H]-	199.15	30932474
DeepCCS	[M+Na]+	174.715	30932474
AllCCS	[M+H]+	169.0	32859911
AllCCS	[M+H-H2O]+	165.9	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	171.2	32859911
AllCCS	[M+Na-2H]-	171.8	32859911
AllCCS	[M+HCOO]-	172.6	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.	3.76 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5118 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	147.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	556.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	208.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	279.6 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	300.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	580.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	630.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	77.7 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	661.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	502.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	494.2 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	78.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Metoclopramide	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC	3594.1	Standard polar	33892256
Metoclopramide	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC	2648.6	Standard non polar	33892256
Metoclopramide	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC	2604.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Metoclopramide,1TMS,isomer #1	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N[Si](C)(C)C)C=C1OC	2716.6	Semi standard non polar	33892256
Metoclopramide,1TMS,isomer #1	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N[Si](C)(C)C)C=C1OC	2546.9	Standard non polar	33892256
Metoclopramide,1TMS,isomer #1	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N[Si](C)(C)C)C=C1OC	3148.1	Standard polar	33892256
Metoclopramide,1TMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N)C=C1OC)[Si](C)(C)C	2453.8	Semi standard non polar	33892256
Metoclopramide,1TMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N)C=C1OC)[Si](C)(C)C	2448.4	Standard non polar	33892256
Metoclopramide,1TMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N)C=C1OC)[Si](C)(C)C	3410.4	Standard polar	33892256
Metoclopramide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C	2580.9	Semi standard non polar	33892256
Metoclopramide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C	2495.3	Standard non polar	33892256
Metoclopramide,2TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C	2908.6	Standard polar	33892256
Metoclopramide,2TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC	2597.0	Semi standard non polar	33892256
Metoclopramide,2TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC	2570.6	Standard non polar	33892256
Metoclopramide,2TMS,isomer #2	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC	2931.7	Standard polar	33892256
Metoclopramide,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C	2543.5	Semi standard non polar	33892256
Metoclopramide,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C	2494.3	Standard non polar	33892256
Metoclopramide,3TMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C	2732.7	Standard polar	33892256
Metoclopramide,1TBDMS,isomer #1	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C=C1OC	2920.6	Semi standard non polar	33892256
Metoclopramide,1TBDMS,isomer #1	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C=C1OC	2774.2	Standard non polar	33892256
Metoclopramide,1TBDMS,isomer #1	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C=C1OC	3196.8	Standard polar	33892256
Metoclopramide,1TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C	2712.6	Semi standard non polar	33892256
Metoclopramide,1TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C	2642.4	Standard non polar	33892256
Metoclopramide,1TBDMS,isomer #2	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C	3414.0	Standard polar	33892256
Metoclopramide,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	2983.0	Semi standard non polar	33892256
Metoclopramide,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	2871.9	Standard non polar	33892256
Metoclopramide,2TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3088.1	Standard polar	33892256
Metoclopramide,2TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3045.5	Semi standard non polar	33892256
Metoclopramide,2TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	2957.6	Standard non polar	33892256
Metoclopramide,2TBDMS,isomer #2	CCN(CC)CCNC(=O)C1=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3058.7	Standard polar	33892256
Metoclopramide,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3131.9	Semi standard non polar	33892256
Metoclopramide,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3069.7	Standard non polar	33892256
Metoclopramide,3TBDMS,isomer #1	CCN(CC)CCN(C(=O)C1=CC(Cl)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3013.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Metoclopramide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-9610000000-b6fe5f492b0d4ca6c150	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Metoclopramide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-10fdf9db1550886fc034	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-fcc278321866ecdee26f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-004i-0193000000-c044c04d9d51d66ba5a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-004i-0290000000-45d3c52d766c4cd8ae93	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-003r-0970000000-2f2d709cad2c27f798e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-001i-0920000000-ccce0f42f04edf0ecfb3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-00lr-0900000000-93aec7dddb8a098f7483	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-e7b25ddf867c24be5347	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-004i-0093000000-dc0ce524de60c6a189a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-004i-0290000000-2bca02d9f4cee5acca4e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-003r-0970000000-50fe530dffb9aa59d433	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-001i-0920000000-0bb9973fdbe0820dc3d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-00lr-0900000000-4cc6fae9bec9d4c40dbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide LC-ESI-ITFT , positive-QTOF	splash10-004i-0090000000-1c4a27b221c7a053d2c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide , positive-QTOF	splash10-0fb9-0595000000-db3b50f051cfcc835a69	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide 15V, Positive-QTOF	splash10-0ufr-0069000000-93c3839d751c69450f14	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide 10V, Positive-QTOF	splash10-0ufr-0069000000-81fd95d3b4b8a739b1b5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide 35V, Positive-QTOF	splash10-004i-0290000000-6741a21b4bd686e97955	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Metoclopramide 75V, Positive-QTOF	splash10-004l-9400000000-e6a69fee2535079fef49	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoclopramide 10V, Positive-QTOF	splash10-0udi-1759000000-14b767e1985b55c13727	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoclopramide 20V, Positive-QTOF	splash10-0ugr-4940000000-2016fe8b0b0d4e5aa870	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoclopramide 40V, Positive-QTOF	splash10-0fk9-9500000000-94bfb5af9b1e4e11a705	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoclopramide 10V, Negative-QTOF	splash10-0002-0190000000-6b24c4fdc3e3fbf344c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoclopramide 20V, Negative-QTOF	splash10-0002-2590000000-1429e8508288721a0e7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Metoclopramide 40V, Negative-QTOF	splash10-0596-9810000000-f5f978ef1ee636729e5f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB01233	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01233	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01233

Phenol Explorer Compound ID

Not Available

FooDB 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

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

Tonini M, Candura SM, Messori E, Rizzi CA: Therapeutic potential of drugs with mixed 5-HT4 agonist/5-HT3 antagonist action in the control of emesis. Pharmacol Res. 1995 May;31(5):257-60. [PubMed:7479521 ]
JUSTIN-BESANCON L, LAVILLE C: [ANTIEMETIC ACTION OF METOCLOPRAMIDE WITH RESPECT TO APOMORPHINE AND HYDERGINE]. C R Seances Soc Biol Fil. 1964;158:723-7. [PubMed:14186927 ]

Enzymes

Enzyme Details

1. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

References

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

Enzyme Details

2. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:: CYP17A1
Uniprot ID:: P05093
Molecular weight:: 57369.995

References

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

Enzyme Details

3. Cytochrome P450 2D6

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

References

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

Enzyme Details

4. D(2) dopamine receptor

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

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
See RE, Lynch AM, Sorg BA: Subchronic administration of clozapine, but not haloperidol or metoclopramide, decreases dopamine D2 receptor messenger RNA levels in the nucleus accumbens and caudate-putamen in rats. Neuroscience. 1996 May;72(1):99-104. [PubMed:8730709 ]
Harrold MW, Sriburi A, Matsumoto K, Miller DD, Farooqui T, Uretsky N: The interaction of ammonium, sulfonium, and sulfide analogues of metoclopramide with the dopamine D2 receptor. J Med Chem. 1993 Oct 15;36(21):3166-70. [PubMed:8230103 ]
Kishibayashi N, Karasawa A: Stimulating effects of KW-5092, a novel gastroprokinetic agent, on the gastric emptying, small intestinal propulsion and colonic propulsion in rats. Jpn J Pharmacol. 1995 Jan;67(1):45-50. [PubMed:7745844 ]
Chemnitius JM, Haselmeyer KH, Gonska BD, Kreuzer H, Zech R: Indirect parasympathomimetic activity of metoclopramide: reversible inhibition of cholinesterases from human central nervous system and blood. Pharmacol Res. 1996 Jul-Aug;34(1-2):65-72. [PubMed:8981558 ]
Dahlof CG, Hargreaves RJ: Pathophysiology and pharmacology of migraine. Is there a place for antiemetics in future treatment strategies? Cephalalgia. 1998 Nov;18(9):593-604. [PubMed:9876882 ]
Hammer D: Gastroesophageal reflux and prokinetic agents. Neonatal Netw. 2005 Mar-Apr;24(2):51-8; quiz 59-62. [PubMed:15835479 ]

Enzyme Details

5. 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

Guillemot J, Compagnon P, Cartier D, Thouennon E, Bastard C, Lihrmann I, Pichon P, Thuillez C, Plouin PF, Bertherat J, Anouar Y, Kuhn JM, Yon L, Lefebvre H: Metoclopramide stimulates catecholamine- and granin-derived peptide secretion from pheochromocytoma cells through activation of serotonin type 4 (5-HT4) receptors. Endocr Relat Cancer. 2009 Mar;16(1):281-90. doi: 10.1677/ERC-08-0190. Epub 2008 Oct 23. [PubMed:18948374 ]

Enzyme Details

6. Cytochrome P450 11B2, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:: CYP11B2
Uniprot ID:: P19099
Molecular weight:: 57559.62

References

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

Enzyme Details

7. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Burger DM, Wiestner T, Hubler M, Binder H, Keiser M, Arnold S: Effect of anticholinergics (atropine, glycopyrrolate) and prokinetics (metoclopramide, cisapride) on gastric motility in beagles and labrador retrievers. J Vet Med A Physiol Pathol Clin Med. 2006 Mar;53(2):97-107. [PubMed:16466463 ]
Hammer D: Gastroesophageal reflux and prokinetic agents. Neonatal Netw. 2005 Mar-Apr;24(2):51-8; quiz 59-62. [PubMed:15835479 ]

Showing metabocard for Metoclopramide (HMDB0015363)

MOL for HMDB0015363 (Metoclopramide)

3D MOL for HMDB0015363 (Metoclopramide)

3D SDF for HMDB0015363 (Metoclopramide)

3D-SDF for HMDB0015363 (Metoclopramide)

PDB for HMDB0015363 (Metoclopramide)

3D PDB for HMDB0015363 (Metoclopramide)

SMILES for HMDB0015363 (Metoclopramide)

INCHI for HMDB0015363 (Metoclopramide)

Structure for HMDB0015363 (Metoclopramide)

3D Structure for HMDB0015363 (Metoclopramide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References