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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:43:39 UTC

Update Date

2021-09-26 23:16:39 UTC

HMDB ID

HMDB0259231

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trimecaine

Description

2-(diethylamino)-N-(2,4,6-trimethylphenyl)ethanimidic acid, also known as mesidicain, belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. Based on a literature review very few articles have been published on 2-(diethylamino)-N-(2,4,6-trimethylphenyl)ethanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trimecaine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trimecaine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259231
     RDKit          3D
Trimecaine
 42 42  0  0  0  0  0  0  0  0999 V2000
   -3.7972   -1.8787    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -0.9440   -0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295    0.3910    0.2416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133    1.1750    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2018    0.7769    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442    1.1228   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928    0.8026    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    0.8656    1.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    0.4641   -0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303    0.1457   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7608    1.1890   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876    2.5216   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621    0.9055   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4984   -0.3470    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9324   -0.6230    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474   -1.3373    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2172   -1.0880   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -2.2175   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5242   -2.9177    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347   -1.8905    1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8518   -1.7425    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268   -1.0548   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -1.3612   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7786    2.2451    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030    1.1939   -1.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858    1.6703    1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9796    0.0907    1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9811    0.3820    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709    0.9491   -1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    2.2306   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.0245    1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    2.4286   -1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    3.0861   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0924    3.0537   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063    1.7082   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1541   -0.0305    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0486   -1.6840    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6022   -0.2992   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -2.3218    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -2.0832   -0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -2.5284    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818   -3.0734   -0.5589 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
  7  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END


  Mrv1652306031606232D          

 18 18  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  4  0  0  0
 17  6  1  0  0  0  0
 17  7  1  0  0  0  0
 17 10  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259231

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CC(O)=NC1=C(C)C=C(C)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O/c1-6-17(7-2)10-14(18)16-15-12(4)8-11(3)9-13(15)5/h8-9H,6-7,10H2,1-5H3,(H,16,18)

> <INCHI_KEY>
GOZBHBFUQHMKQB-UHFFFAOYSA-N

> <FORMULA>
C15H24N2O

> <MOLECULAR_WEIGHT>
248.37

> <EXACT_MASS>
248.188863401

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.970062532261736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(diethylamino)-N-(2,4,6-trimethylphenyl)ethanimidic acid

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
1.4376556938305043

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4502676299030286

> <JCHEM_PKA_STRONGEST_BASIC>
8.623226301358876

> <JCHEM_POLAR_SURFACE_AREA>
35.83

> <JCHEM_REFRACTIVITY>
79.72590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(diethylamino)-N-(2,4,6-trimethylphenyl)ethanimidic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0259231
     RDKit          3D
Trimecaine
 42 42  0  0  0  0  0  0  0  0999 V2000
   -3.7972   -1.8787    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -0.9440   -0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295    0.3910    0.2416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133    1.1750    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2018    0.7769    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442    1.1228   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928    0.8026    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    0.8656    1.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    0.4641   -0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303    0.1457   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7608    1.1890   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876    2.5216   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621    0.9055   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4984   -0.3470    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9324   -0.6230    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474   -1.3373    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2172   -1.0880   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -2.2175   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5242   -2.9177    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347   -1.8905    1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8518   -1.7425    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268   -1.0548   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -1.3612   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7786    2.2451    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030    1.1939   -1.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858    1.6703    1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9796    0.0907    1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9811    0.3820    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709    0.9491   -1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    2.2306   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.0245    1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    2.4286   -1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    3.0861   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0924    3.0537   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063    1.7082   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1541   -0.0305    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0486   -1.6840    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6022   -0.2992   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -2.3218    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -2.0832   -0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -2.5284    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818   -3.0734   -0.5589 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
  7  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6    1   17                                                       
CONECT    7    2   17                                                       
CONECT    8   11   12                                                       
CONECT    9   11   13                                                       
CONECT   10   14   17                                                       
CONECT   11    3    8    9                                                  
CONECT   12    4    8   15                                                  
CONECT   13    5    9   15                                                  
CONECT   14   10   16   18                                                  
CONECT   15   12   13   16                                                  
CONECT   16   14   15                                                       
CONECT   17    6    7   10                                                  
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0259231
HETATM    1  C1  UNL     1      -3.797  -1.879   0.485  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.859  -0.944  -0.221  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.830   0.391   0.242  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.013   1.175   0.034  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.202   0.777   0.844  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.744   1.123  -0.358  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.393   0.803   0.054  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.067   0.866   1.402  1.00  0.00           O  
HETATM    9  N2  UNL     1       0.503   0.464  -0.803  1.00  0.00           N  
HETATM   10  C7  UNL     1       1.830   0.146  -0.494  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.761   1.189  -0.593  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.288   2.522  -1.025  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.062   0.906  -0.290  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.498  -0.347   0.103  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.932  -0.623   0.429  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.547  -1.337   0.183  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.217  -1.088  -0.115  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.294  -2.218  -0.006  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.524  -2.918   0.121  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.635  -1.890   1.567  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.852  -1.742   0.176  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.027  -1.055  -1.315  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.819  -1.361  -0.068  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.779   2.245   0.293  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.203   1.194  -1.060  1.00  0.00           H  
HETATM   26  H8  UNL     1      -5.686   1.670   1.349  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.980   0.091   1.693  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.981   0.382   0.160  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.871   0.949  -1.472  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.899   2.231  -0.268  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.001   0.025   1.983  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.447   2.429  -1.747  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.994   3.086  -0.100  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.092   3.054  -1.597  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.806   1.708  -0.366  1.00  0.00           H  
HETATM   36  H18 UNL     1       6.154  -0.030   1.362  1.00  0.00           H  
HETATM   37  H19 UNL     1       6.049  -1.684   0.640  1.00  0.00           H  
HETATM   38  H20 UNL     1       6.602  -0.299  -0.376  1.00  0.00           H  
HETATM   39  H21 UNL     1       3.879  -2.322   0.485  1.00  0.00           H  
HETATM   40  H22 UNL     1       0.332  -2.083  -0.521  1.00  0.00           H  
HETATM   41  H23 UNL     1       1.088  -2.528   1.040  1.00  0.00           H  
HETATM   42  H24 UNL     1       1.782  -3.073  -0.559  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    6
CONECT    4    5   24   25
CONECT    5   26   27   28
CONECT    6    7   29   30
CONECT    7    8    9    9
CONECT    8   31
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   13
CONECT   12   32   33   34
CONECT   13   14   14   35
CONECT   14   15   16
CONECT   15   36   37   38
CONECT   16   17   17   39
CONECT   17   18
CONECT   18   40   41   42
END

HMDB0259231
     RDKit          3D
Trimecaine
 42 42  0  0  0  0  0  0  0  0999 V2000
   -3.7972   -1.8787    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8588   -0.9440   -0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295    0.3910    0.2416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133    1.1750    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2018    0.7769    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442    1.1228   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928    0.8026    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    0.8656    1.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    0.4641   -0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303    0.1457   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7608    1.1890   -0.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876    2.5216   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621    0.9055   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4984   -0.3470    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9324   -0.6230    0.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474   -1.3373    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2172   -1.0880   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2939   -2.2175   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5242   -2.9177    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347   -1.8905    1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8518   -1.7425    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0268   -1.0548   -1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8192   -1.3612   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7786    2.2451    0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2030    1.1939   -1.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858    1.6703    1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9796    0.0907    1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9811    0.3820    0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709    0.9491   -1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8986    2.2306   -0.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.0245    1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475    2.4286   -1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    3.0861   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0924    3.0537   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063    1.7082   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1541   -0.0305    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0486   -1.6840    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6022   -0.2992   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -2.3218    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -2.0832   -0.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0881   -2.5284    1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818   -3.0734   -0.5589 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
  7  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Mesidicain	Kegg
Mesocain	Kegg
2-(Diethylamino)-N-(2,4,6-trimethylphenyl)ethanimidate	Generator
Mesocaine	MeSH
Monohydrochloride, trimecaine	MeSH
Trimecaine monohydrochloride	MeSH

Chemical Formula

C₁₅H₂₄N₂O

Average Molecular Weight

248.37

Monoisotopic Molecular Weight

248.188863401

IUPAC Name

2-(diethylamino)-N-(2,4,6-trimethylphenyl)ethanimidic acid

Traditional Name

2-(diethylamino)-N-(2,4,6-trimethylphenyl)ethanimidic acid

CAS Registry Number

Not Available

SMILES

CCN(CC)CC(O)=NC1=C(C)C=C(C)C=C1C

InChI Identifier

InChI=1S/C15H24N2O/c1-6-17(7-2)10-14(18)16-15-12(4)8-11(3)9-13(15)5/h8-9H,6-7,10H2,1-5H3,(H,16,18)

InChI Key

GOZBHBFUQHMKQB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Anilide
N-arylamide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.61	ALOGPS
logP	1.44	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	8.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.73 m³·mol⁻¹	ChemAxon
Polarizability	29.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	164.627	30932474
DeepCCS	[M-H]-	162.269	30932474
DeepCCS	[M-2H]-	195.155	30932474
DeepCCS	[M+Na]+	170.721	30932474
AllCCS	[M+H]+	160.2	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.2	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	165.3	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimecaine	CCN(CC)CC(O)=NC1=C(C)C=C(C)C=C1C	2380.4	Standard polar	33892256
Trimecaine	CCN(CC)CC(O)=NC1=C(C)C=C(C)C=C1C	1906.1	Standard non polar	33892256
Trimecaine	CCN(CC)CC(O)=NC1=C(C)C=C(C)C=C1C	1913.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trimecaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-053i-9600000000-1041a2284ca6d68a8583	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimecaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimecaine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimecaine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	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 - Trimecaine 10V, Positive-QTOF	splash10-000i-9110000000-80c7fdaa71575b95ba63	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimecaine 20V, Positive-QTOF	splash10-000i-9100000000-884fd6ce0210ed4881ab	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimecaine 40V, Positive-QTOF	splash10-0a4r-9000000000-04b08f32f1cd831deb07	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimecaine 10V, Negative-QTOF	splash10-0002-0190000000-514d5312f32601bb8921	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimecaine 20V, Negative-QTOF	splash10-000t-1970000000-07b3100144f7da4d8c77	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimecaine 40V, Negative-QTOF	splash10-001i-4900000000-ad3ede9c0cb5d592c74e	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

11533

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Trimecaine (HMDB0259231)

MOL for HMDB0259231 (Trimecaine)

3D MOL for HMDB0259231 (Trimecaine)

3D SDF for HMDB0259231 (Trimecaine)

3D-SDF for HMDB0259231 (Trimecaine)

PDB for HMDB0259231 (Trimecaine)

3D PDB for HMDB0259231 (Trimecaine)

SMILES for HMDB0259231 (Trimecaine)

INCHI for HMDB0259231 (Trimecaine)

Structure for HMDB0259231 (Trimecaine)

3D Structure for HMDB0259231 (Trimecaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra