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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014800

Secondary Accession Numbers

HMDB14800

Metabolite Identification

Common Name

Trimethobenzamide

Description

Trimethobenzamide, also known as ametik damla or T-gen, belongs to the class of organic compounds known as n-benzylbenzamides. N-benzylbenzamides are compounds containing a benzamide moiety that is N-linked to a benzyl group. Trimethobenzamide is a drug which is used for the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis. Based on a literature review a significant number of articles have been published on Trimethobenzamide.

Structure

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

662
  Mrv0541 02231214522D          

 28 29  0  0  0  0            999 V2000
    7.3659    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -4.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2 21  1  0  0  0  0
  2 26  1  0  0  0  0
  3 22  1  0  0  0  0
  3 27  1  0  0  0  0
  4 23  1  0  0  0  0
  4 28  1  0  0  0  0
  5 18  2  0  0  0  0
  6  8  1  0  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
  7 10  1  0  0  0  0
  7 18  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 19  2  0  0  0  0
 13 20  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 19 22  1  0  0  0  0
 20 21  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END

HMDB0014800
     RDKit          3D
Trimethobenzamide
 56 57  0  0  0  0  0  0  0  0999 V2000
   -4.4430    3.4831    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0737    2.7313    0.6790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7144    1.4878    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6238    0.8277    0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654   -0.4357    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1197   -1.1248    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -0.7055    1.8868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -2.2318    0.1839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -2.9077    0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8609   -2.0358    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -2.0379    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -1.2467    1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.4154    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469    0.3996    0.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2711    0.3752    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4187    1.2835    0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0835    1.0123   -0.5890 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8085   -0.2254   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8733    2.1315   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012   -0.4052   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -1.2039   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0257   -1.0077   -0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218   -0.3519   -1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9162   -0.8792   -2.2508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313   -2.1440   -2.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809    0.9185   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872    1.5745   -1.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8382    1.3339   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389    4.1822    1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500    2.8425    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1790    4.1594    2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.2813    1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -2.5673   -0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620   -3.0142    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834   -3.8750    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -2.7006    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8196   -1.2790    2.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8387    0.7272    1.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -0.6557    1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1079    2.3522    0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595    1.1794    1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7210   -0.7848   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5337   -0.8015    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8960    0.0331   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7306    2.2370   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3223    3.0823   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2783    1.9313   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004    0.2485   -1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1939   -1.1629   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849   -1.9961   -1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3091   -2.9005   -2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6002   -2.4925   -3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8803   -2.0820   -3.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8490    0.3033   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9182    2.0278    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6943    1.5242   -1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 13 20  1  0
 20 21  2  0
  5 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 27  1  0
 27 28  1  0
 26  3  1  0
 21 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
M  END

662
  Mrv0541 02231214522D          

 28 29  0  0  0  0            999 V2000
    7.3659    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -4.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    4.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2 21  1  0  0  0  0
  2 26  1  0  0  0  0
  3 22  1  0  0  0  0
  3 27  1  0  0  0  0
  4 23  1  0  0  0  0
  4 28  1  0  0  0  0
  5 18  2  0  0  0  0
  6  8  1  0  0  0  0
  6 24  1  0  0  0  0
  6 25  1  0  0  0  0
  7 10  1  0  0  0  0
  7 18  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 12 16  2  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 19  2  0  0  0  0
 13 20  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 19 22  1  0  0  0  0
 20 21  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014800

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24)

> <INCHI_KEY>
FEZBIKUBAYAZIU-UHFFFAOYSA-N

> <FORMULA>
C21H28N2O5

> <MOLECULAR_WEIGHT>
388.4574

> <EXACT_MASS>
388.199822016

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
43.193858496554896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
2.159994753

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.361793094120586

> <JCHEM_PKA_STRONGEST_BASIC>
8.771535725322801

> <JCHEM_POLAR_SURFACE_AREA>
69.26

> <JCHEM_REFRACTIVITY>
108.51759999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethobenzamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014800
     RDKit          3D
Trimethobenzamide
 56 57  0  0  0  0  0  0  0  0999 V2000
   -4.4430    3.4831    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0737    2.7313    0.6790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7144    1.4878    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6238    0.8277    0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654   -0.4357    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1197   -1.1248    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -0.7055    1.8868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -2.2318    0.1839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -2.9077    0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8609   -2.0358    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -2.0379    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -1.2467    1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.4154    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469    0.3996    0.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2711    0.3752    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4187    1.2835    0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0835    1.0123   -0.5890 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8085   -0.2254   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8733    2.1315   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012   -0.4052   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -1.2039   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0257   -1.0077   -0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218   -0.3519   -1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9162   -0.8792   -2.2508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313   -2.1440   -2.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809    0.9185   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872    1.5745   -1.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8382    1.3339   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389    4.1822    1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500    2.8425    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1790    4.1594    2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.2813    1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -2.5673   -0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620   -3.0142    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834   -3.8750    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -2.7006    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8196   -1.2790    2.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8387    0.7272    1.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -0.6557    1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1079    2.3522    0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595    1.1794    1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7210   -0.7848   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5337   -0.8015    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8960    0.0331   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7306    2.2370   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3223    3.0823   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2783    1.9313   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004    0.2485   -1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1939   -1.1629   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849   -1.9961   -1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3091   -2.9005   -2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6002   -2.4925   -3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8803   -2.0820   -3.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8490    0.3033   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9182    2.0278    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6943    1.5242   -1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 13 20  1  0
 20 21  2  0
  5 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 27  1  0
 27 28  1  0
 26  3  1  0
 21 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 662                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.750   3.850   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414  -6.160   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748  -6.160   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081  -7.700   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.748  -0.770   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      15.083   7.700   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.415  -0.770   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      15.083   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.750   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.748  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.750   8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.417   8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.080  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.082  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.748  -8.470   0.000  0.00  0.00           C+0
CONECT    1   11   12                                                       
CONECT    2   21   26                                                       
CONECT    3   22   27                                                       
CONECT    4   23   28                                                       
CONECT    5   18                                                            
CONECT    6    8   24   25                                                  
CONECT    7   10   18                                                       
CONECT    8    6   11                                                       
CONECT    9   10   14   15                                                  
CONECT   10    7    9                                                       
CONECT   11    1    8                                                       
CONECT   12    1   16   17                                                  
CONECT   13   18   19   20                                                  
CONECT   14    9   16                                                       
CONECT   15    9   17                                                       
CONECT   16   12   14                                                       
CONECT   17   12   15                                                       
CONECT   18    5    7   13                                                  
CONECT   19   13   22                                                       
CONECT   20   13   21                                                       
CONECT   21    2   20   23                                                  
CONECT   22    3   19   23                                                  
CONECT   23    4   21   22                                                  
CONECT   24    6                                                            
CONECT   25    6                                                            
CONECT   26    2                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0014800
HETATM    1  C1  UNL     1      -4.443   3.483   1.666  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.074   2.731   0.679  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.714   1.488   0.213  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.624   0.828   0.717  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.265  -0.436   0.237  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.120  -1.125   0.789  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.648  -0.705   1.887  1.00  0.00           O  
HETATM    8  N1  UNL     1      -1.495  -2.232   0.184  1.00  0.00           N  
HETATM    9  C6  UNL     1      -0.346  -2.908   0.771  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.861  -2.036   0.565  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.898  -2.038   1.478  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.016  -1.247   1.313  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.142  -0.415   0.221  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.247   0.400   0.012  1.00  0.00           O  
HETATM   15  C11 UNL     1       5.271   0.375   0.951  1.00  0.00           C  
HETATM   16  C12 UNL     1       6.419   1.283   0.644  1.00  0.00           C  
HETATM   17  N2  UNL     1       7.084   1.012  -0.589  1.00  0.00           N  
HETATM   18  C13 UNL     1       7.808  -0.225  -0.617  1.00  0.00           C  
HETATM   19  C14 UNL     1       7.873   2.132  -1.066  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.101  -0.405  -0.708  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.985  -1.204  -0.531  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.026  -1.008  -0.752  1.00  0.00           C  
HETATM   23  C18 UNL     1      -5.122  -0.352  -1.263  1.00  0.00           C  
HETATM   24  O4  UNL     1      -5.916  -0.879  -2.251  1.00  0.00           O  
HETATM   25  C19 UNL     1      -5.631  -2.144  -2.791  1.00  0.00           C  
HETATM   26  C20 UNL     1      -5.481   0.918  -0.779  1.00  0.00           C  
HETATM   27  O5  UNL     1      -6.587   1.575  -1.298  1.00  0.00           O  
HETATM   28  C21 UNL     1      -7.838   1.334  -0.652  1.00  0.00           C  
HETATM   29  H1  UNL     1      -3.739   4.182   1.143  1.00  0.00           H  
HETATM   30  H2  UNL     1      -3.950   2.843   2.396  1.00  0.00           H  
HETATM   31  H3  UNL     1      -5.179   4.159   2.162  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.031   1.281   1.494  1.00  0.00           H  
HETATM   33  H5  UNL     1      -1.890  -2.567  -0.729  1.00  0.00           H  
HETATM   34  H6  UNL     1      -0.562  -3.014   1.855  1.00  0.00           H  
HETATM   35  H7  UNL     1      -0.183  -3.875   0.266  1.00  0.00           H  
HETATM   36  H8  UNL     1       1.784  -2.701   2.336  1.00  0.00           H  
HETATM   37  H9  UNL     1       3.820  -1.279   2.063  1.00  0.00           H  
HETATM   38  H10 UNL     1       4.839   0.727   1.925  1.00  0.00           H  
HETATM   39  H11 UNL     1       5.611  -0.656   1.137  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.108   2.352   0.649  1.00  0.00           H  
HETATM   41  H13 UNL     1       7.160   1.179   1.467  1.00  0.00           H  
HETATM   42  H14 UNL     1       7.721  -0.785  -1.562  1.00  0.00           H  
HETATM   43  H15 UNL     1       7.534  -0.802   0.286  1.00  0.00           H  
HETATM   44  H16 UNL     1       8.896   0.033  -0.514  1.00  0.00           H  
HETATM   45  H17 UNL     1       8.731   2.237  -0.371  1.00  0.00           H  
HETATM   46  H18 UNL     1       7.322   3.082  -1.025  1.00  0.00           H  
HETATM   47  H19 UNL     1       8.278   1.931  -2.078  1.00  0.00           H  
HETATM   48  H20 UNL     1       2.200   0.248  -1.565  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.194  -1.163  -1.285  1.00  0.00           H  
HETATM   50  H22 UNL     1      -3.785  -1.996  -1.166  1.00  0.00           H  
HETATM   51  H23 UNL     1      -5.309  -2.901  -2.070  1.00  0.00           H  
HETATM   52  H24 UNL     1      -6.600  -2.492  -3.267  1.00  0.00           H  
HETATM   53  H25 UNL     1      -4.880  -2.082  -3.620  1.00  0.00           H  
HETATM   54  H26 UNL     1      -7.849   0.303  -0.215  1.00  0.00           H  
HETATM   55  H27 UNL     1      -7.918   2.028   0.216  1.00  0.00           H  
HETATM   56  H28 UNL     1      -8.694   1.524  -1.304  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   32
CONECT    5    6   22   22
CONECT    6    7    7    8
CONECT    8    9   33
CONECT    9   10   34   35
CONECT   10   11   11   21
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14   20
CONECT   14   15
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   18   19
CONECT   18   42   43   44
CONECT   19   45   46   47
CONECT   20   21   21   48
CONECT   21   49
CONECT   22   23   50
CONECT   23   24   26   26
CONECT   24   25
CONECT   25   51   52   53
CONECT   26   27
CONECT   27   28
CONECT   28   54   55   56
END

HMDB0014800
     RDKit          3D
Trimethobenzamide
 56 57  0  0  0  0  0  0  0  0999 V2000
   -4.4430    3.4831    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0737    2.7313    0.6790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7144    1.4878    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6238    0.8277    0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2654   -0.4357    0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1197   -1.1248    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -0.7055    1.8868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -2.2318    0.1839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -2.9077    0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8609   -2.0358    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -2.0379    1.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -1.2467    1.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418   -0.4154    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2469    0.3996    0.0121 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2711    0.3752    0.9509 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4187    1.2835    0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0835    1.0123   -0.5890 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8085   -0.2254   -0.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8733    2.1315   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1012   -0.4052   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -1.2039   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0257   -1.0077   -0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218   -0.3519   -1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9162   -0.8792   -2.2508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313   -2.1440   -2.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4809    0.9185   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5872    1.5745   -1.2980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8382    1.3339   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389    4.1822    1.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500    2.8425    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1790    4.1594    2.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    1.2813    1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -2.5673   -0.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620   -3.0142    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834   -3.8750    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7836   -2.7006    2.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8196   -1.2790    2.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8387    0.7272    1.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -0.6557    1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1079    2.3522    0.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1595    1.1794    1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7210   -0.7848   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5337   -0.8015    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8960    0.0331   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7306    2.2370   -0.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3223    3.0823   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2783    1.9313   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004    0.2485   -1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1939   -1.1629   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849   -1.9961   -1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3091   -2.9005   -2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6002   -2.4925   -3.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8803   -2.0820   -3.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8490    0.3033   -0.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9182    2.0278    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6943    1.5242   -1.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 13 20  1  0
 20 21  2  0
  5 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 27  1  0
 27 28  1  0
 26  3  1  0
 21 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[[4-(2-Dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide	ChEBI
Trimethobenzamidum	ChEBI
Trimetobenzamida	ChEBI
Ametik damla	Kegg
T-Gen	HMDB
Tebamide	HMDB
Tigan	HMDB
Trimethobenzamide monohydrochloride	HMDB
Ticon	HMDB

Chemical Formula

C₂₁H₂₈N₂O₅

Average Molecular Weight

388.4574

Monoisotopic Molecular Weight

388.199822016

IUPAC Name

N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide

Traditional Name

trimethobenzamide

CAS Registry Number

138-56-7

SMILES

COC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1

InChI Identifier

InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24)

InChI Key

FEZBIKUBAYAZIU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-benzylbenzamides. N-benzylbenzamides are compounds containing a benzamide moiety that is N-linked to a benzyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

N-benzylbenzamides

Alternative Parents

Substituents

N-benzylbenzamide
Anisole
Benzoyl
Phenol ether
Methoxybenzene
Phenoxy compound
Alkyl aryl ether
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxylic acid derivative
Ether
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:27796 )
benzamides (CHEBI:27796 )

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: HMDB0014800)

Source

Exogenous

Exogenous (HMDB: HMDB0014800)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	188.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.04 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	193.34	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000724

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.44	ALOGPS
logP	2.16	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.26 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.52 m³·mol⁻¹	ChemAxon
Polarizability	43.19 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	192.594	31661259
DarkChem	[M-H]-	191.991	31661259
DeepCCS	[M+H]+	193.813	30932474
DeepCCS	[M-H]-	191.455	30932474
DeepCCS	[M-2H]-	225.618	30932474
DeepCCS	[M+Na]+	200.846	30932474
AllCCS	[M+H]+	195.8	32859911
AllCCS	[M+H-H2O]+	193.2	32859911
AllCCS	[M+NH4]+	198.1	32859911
AllCCS	[M+Na]+	198.8	32859911
AllCCS	[M-H]-	198.2	32859911
AllCCS	[M+Na-2H]-	198.8	32859911
AllCCS	[M+HCOO]-	199.6	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.	4.17 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3204 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	95.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1254.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	194.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	153.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	271.6 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	361.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	749.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	765.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	274.6 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	1066.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	419.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	30.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimethobenzamide	COC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1	4033.7	Standard polar	33892256
Trimethobenzamide	COC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1	3321.7	Standard non polar	33892256
Trimethobenzamide	COC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1	3330.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trimethobenzamide,1TMS,isomer #1	COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C)=CC(OC)=C1OC	3096.8	Semi standard non polar	33892256
Trimethobenzamide,1TMS,isomer #1	COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C)=CC(OC)=C1OC	3122.7	Standard non polar	33892256
Trimethobenzamide,1TMS,isomer #1	COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C)=CC(OC)=C1OC	3898.8	Standard polar	33892256
Trimethobenzamide,1TBDMS,isomer #1	COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3351.2	Semi standard non polar	33892256
Trimethobenzamide,1TBDMS,isomer #1	COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3274.0	Standard non polar	33892256
Trimethobenzamide,1TBDMS,isomer #1	COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	3954.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethobenzamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9503000000-470bcb74571cf77936cc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethobenzamide 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 - Trimethobenzamide 10V, Positive-QTOF	splash10-000i-1509000000-a0aecd823447fda8b581	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Positive-QTOF	splash10-00fr-7903000000-371796a4982a6ca18e8d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Positive-QTOF	splash10-00fr-9600000000-3c0537fa07832854c2bd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 10V, Negative-QTOF	splash10-000i-0019000000-3f8b8afc43431a25c23f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Negative-QTOF	splash10-0i09-1239000000-8954d657acecb2570aec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Negative-QTOF	splash10-0h4o-6972000000-b5809e22e16fd9ec1ad7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 10V, Positive-QTOF	splash10-000i-1009000000-141c83bfee0ad68e6a87	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Positive-QTOF	splash10-00g0-5529000000-9b1cb5630b9473bf9bf4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Positive-QTOF	splash10-00di-9210000000-c806a75ff840adac07b5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 10V, Negative-QTOF	splash10-014r-0009000000-5c685906db39ec31b792	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Negative-QTOF	splash10-0uyr-1149000000-c28c4f592811edfc3418	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Negative-QTOF	splash10-0udi-2239000000-657a89bdcdadde450f80	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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 DB00662	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00662	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00662

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5375

KEGG Compound ID

C07178

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trimethobenzamide

METLIN ID

Not Available

PubChem Compound

5577

PDB ID

Not Available

ChEBI ID

27796

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

Dundee JW, Halliday F, Nicholl RM, Moore J: Studies of drugs given before anaesthesia. X. Two non-phenothiazine anti-emetics--cyclizine and trimethobenzamide. Br J Anaesth. 1966 Jan;38(1):50-7. [PubMed:5908416 ]
Hurley JD, Eshelman FN: Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6. [PubMed:7400373 ]

Showing metabocard for Trimethobenzamide (HMDB0014800)

MOL for HMDB0014800 (Trimethobenzamide)

3D MOL for HMDB0014800 (Trimethobenzamide)

3D SDF for HMDB0014800 (Trimethobenzamide)

3D-SDF for HMDB0014800 (Trimethobenzamide)

PDB for HMDB0014800 (Trimethobenzamide)

3D PDB for HMDB0014800 (Trimethobenzamide)

SMILES for HMDB0014800 (Trimethobenzamide)

INCHI for HMDB0014800 (Trimethobenzamide)

Structure for HMDB0014800 (Trimethobenzamide)

3D Structure for HMDB0014800 (Trimethobenzamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra