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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:39:32 UTC

Update Date

2021-09-26 23:16:05 UTC

HMDB ID

HMDB0258868

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tetracaine

Description

Tetracaine, also known as amethocaine, belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Based on a literature review a significant number of articles have been published on Tetracaine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tetracaine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tetracaine 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

HMDB0258868
     RDKit          3D
Tetracaine
 43 43  0  0  0  0  0  0  0  0999 V2000
    6.4748    1.0141    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4229   -0.4230    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8085   -1.2920   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4041   -0.8563   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906   -0.9519    0.7380 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137   -0.5686    0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429   -0.6561    1.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024   -0.2855    1.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.1525    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    0.5266    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381    0.4452    1.5318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4898    0.9730   -0.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8436    1.3470   -0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6991    0.1721   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1200    0.4795   -0.4825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5362    0.7113   -1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8259   -0.6264    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546    0.2303   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6808   -0.1282   -0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6719    1.0089   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973    1.4944    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3076    1.5486    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -0.7554    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730   -0.5453    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8206   -2.3373    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962   -1.2397   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4752    0.1867   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9918   -1.4500   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0090   -1.2890    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.9916    2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173   -0.3535    2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0721    2.2282   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    1.6337   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399   -0.2341    0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4448   -0.6695   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2740    1.7163   -2.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1202   -0.1061   -2.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6381    0.5953   -1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512   -1.0707    0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9684   -1.4210   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8538   -0.3163    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0811    0.5749   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3074   -0.0616   -1.4632 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  9 18  1  0
 18 19  2  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
M  END


  Mrv1533004261507212D          

 19 19  0  0  0  0            999 V2000
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
    0.0000    3.3000    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    2.0625    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
    0.7145    2.0625    0.0000 C   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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258868

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3

> <INCHI_KEY>
GKCBAIGFKIBETG-UHFFFAOYSA-N

> <FORMULA>
C15H24N2O2

> <MOLECULAR_WEIGHT>
264.369

> <EXACT_MASS>
264.183778021

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.903711609672246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(dimethylamino)ethyl 4-(butylamino)benzoate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
2.7920444443333325

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.417555490390724

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
80.16980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetracaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258868
     RDKit          3D
Tetracaine
 43 43  0  0  0  0  0  0  0  0999 V2000
    6.4748    1.0141    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4229   -0.4230    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8085   -1.2920   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4041   -0.8563   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906   -0.9519    0.7380 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137   -0.5686    0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429   -0.6561    1.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024   -0.2855    1.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.1525    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    0.5266    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381    0.4452    1.5318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4898    0.9730   -0.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8436    1.3470   -0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6991    0.1721   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1200    0.4795   -0.4825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5362    0.7113   -1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8259   -0.6264    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546    0.2303   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6808   -0.1282   -0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6719    1.0089   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973    1.4944    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3076    1.5486    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -0.7554    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730   -0.5453    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8206   -2.3373    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962   -1.2397   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4752    0.1867   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9918   -1.4500   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0090   -1.2890    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.9916    2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173   -0.3535    2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0721    2.2282   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    1.6337   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399   -0.2341    0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4448   -0.6695   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2740    1.7163   -2.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1202   -0.1061   -2.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6381    0.5953   -1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512   -1.0707    0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9684   -1.4210   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8538   -0.3163    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0811    0.5749   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3074   -0.0616   -1.4632 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  9 18  1  0
 18 19  2  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -4.001   6.930   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0258868
HETATM    1  C1  UNL     1       6.475   1.014   0.489  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.423  -0.423   0.971  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.809  -1.292  -0.103  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.404  -0.856  -0.446  1.00  0.00           C  
HETATM    5  N1  UNL     1       3.591  -0.952   0.738  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.214  -0.569   0.632  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.443  -0.656   1.766  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.102  -0.286   1.677  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.438   0.152   0.501  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.856   0.527   0.482  1.00  0.00           C  
HETATM   11  O1  UNL     1      -2.538   0.445   1.532  1.00  0.00           O  
HETATM   12  O2  UNL     1      -2.490   0.973  -0.659  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.844   1.347  -0.754  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.699   0.172  -0.406  1.00  0.00           C  
HETATM   15  N2  UNL     1      -6.120   0.480  -0.483  1.00  0.00           N  
HETATM   16  C12 UNL     1      -6.536   0.711  -1.853  1.00  0.00           C  
HETATM   17  C13 UNL     1      -6.826  -0.626   0.135  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.355   0.230  -0.616  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.681  -0.128  -0.560  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.672   1.009  -0.602  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.497   1.494   0.746  1.00  0.00           H  
HETATM   22  H3  UNL     1       7.308   1.549   0.981  1.00  0.00           H  
HETATM   23  H4  UNL     1       7.485  -0.755   1.057  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.873  -0.545   1.903  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.821  -2.337   0.295  1.00  0.00           H  
HETATM   26  H7  UNL     1       6.396  -1.240  -1.047  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.475   0.187  -0.821  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.992  -1.450  -1.282  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.009  -1.289   1.618  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.799  -0.992   2.727  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.517  -0.354   2.579  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.072   2.228  -0.121  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.022   1.634  -1.812  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.540  -0.234   0.610  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.445  -0.670  -1.107  1.00  0.00           H  
HETATM   36  H17 UNL     1      -6.274   1.716  -2.182  1.00  0.00           H  
HETATM   37  H18 UNL     1      -6.120  -0.106  -2.469  1.00  0.00           H  
HETATM   38  H19 UNL     1      -7.638   0.595  -1.882  1.00  0.00           H  
HETATM   39  H20 UNL     1      -6.251  -1.071   0.963  1.00  0.00           H  
HETATM   40  H21 UNL     1      -6.968  -1.421  -0.648  1.00  0.00           H  
HETATM   41  H22 UNL     1      -7.854  -0.316   0.440  1.00  0.00           H  
HETATM   42  H23 UNL     1      -0.081   0.575  -1.530  1.00  0.00           H  
HETATM   43  H24 UNL     1       2.307  -0.062  -1.463  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29
CONECT    6    7    7   19
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   18
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   17
CONECT   16   36   37   38
CONECT   17   39   40   41
CONECT   18   19   19   42
CONECT   19   43
END

HMDB0258868
     RDKit          3D
Tetracaine
 43 43  0  0  0  0  0  0  0  0999 V2000
    6.4748    1.0141    0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4229   -0.4230    0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8085   -1.2920   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4041   -0.8563   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906   -0.9519    0.7380 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137   -0.5686    0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429   -0.6561    1.7664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024   -0.2855    1.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.1525    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    0.5266    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381    0.4452    1.5318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4898    0.9730   -0.6593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8436    1.3470   -0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6991    0.1721   -0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1200    0.4795   -0.4825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5362    0.7113   -1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8259   -0.6264    0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546    0.2303   -0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6808   -0.1282   -0.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6719    1.0089   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973    1.4944    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3076    1.5486    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -0.7554    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8730   -0.5453    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8206   -2.3373    0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3962   -1.2397   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4752    0.1867   -0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9918   -1.4500   -1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0090   -1.2890    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.9916    2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5173   -0.3535    2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0721    2.2282   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    1.6337   -1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399   -0.2341    0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4448   -0.6695   -1.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2740    1.7163   -2.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1202   -0.1061   -2.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6381    0.5953   -1.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2512   -1.0707    0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9684   -1.4210   -0.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8538   -0.3163    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0811    0.5749   -1.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3074   -0.0616   -1.4632 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  9 18  1  0
 18 19  2  0
 19  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(Dimethylamino)ethyl p-(butylamino)benzoate	ChEBI
Amethocaine	ChEBI
Diaethylaminoaethanol ester der p-butylaminobenzoesaeure	ChEBI
p-(Butylamino)benzoic acid beta-(dimethylamino)ethyl ester	ChEBI
p-Butylaminobenzoyl-2-dimethylaminoethanol	ChEBI
Tetracaina	ChEBI
Tetracainum	ChEBI
2-(Dimethylamino)ethyl p-(butylamino)benzoic acid	Generator
p-(Butylamino)benzoate b-(dimethylamino)ethyl ester	Generator
p-(Butylamino)benzoate beta-(dimethylamino)ethyl ester	Generator
p-(Butylamino)benzoate β-(dimethylamino)ethyl ester	Generator
p-(Butylamino)benzoic acid b-(dimethylamino)ethyl ester	Generator
p-(Butylamino)benzoic acid β-(dimethylamino)ethyl ester	Generator
Ametop	MeSH
Dicaine	MeSH
Hydrochloride, tetrracaine	MeSH
Pantocaine	MeSH
Pontocaine	MeSH
Tetracaine monohydrochloride	MeSH
Tetrakain	MeSH
Tetrracaine hydrochloride	MeSH
2-(Dimethylamino)ethyl 4-(butylamino)benzoic acid	Generator

Chemical Formula

C₁₅H₂₄N₂O₂

Average Molecular Weight

264.369

Monoisotopic Molecular Weight

264.183778021

IUPAC Name

2-(dimethylamino)ethyl 4-(butylamino)benzoate

Traditional Name

tetracaine

CAS Registry Number

Not Available

SMILES

CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C

InChI Identifier

InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3

InChI Key

GKCBAIGFKIBETG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Phenylalkylamine
Secondary aliphatic/aromatic amine
Carboxylic acid ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Secondary amine
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Amine
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:9468 )
benzoate ester (CHEBI:9468 )

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	3.54	ALOGPS
logP	2.79	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	80.17 m³·mol⁻¹	ChemAxon
Polarizability	31.9 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]+	166.287	30932474
DeepCCS	[M-H]-	163.929	30932474
DeepCCS	[M-2H]-	196.815	30932474
DeepCCS	[M+Na]+	172.381	30932474
AllCCS	[M+H]+	165.4	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	168.4	32859911
AllCCS	[M+Na]+	169.3	32859911
AllCCS	[M-H]-	168.0	32859911
AllCCS	[M+Na-2H]-	168.7	32859911
AllCCS	[M+HCOO]-	169.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetracaine	CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C	2896.3	Standard polar	33892256
Tetracaine	CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C	2150.3	Standard non polar	33892256
Tetracaine	CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C	2280.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetracaine,1TMS,isomer #1	CCCCN(C1=CC=C(C(=O)OCCN(C)C)C=C1)[Si](C)(C)C	2212.2	Semi standard non polar	33892256
Tetracaine,1TMS,isomer #1	CCCCN(C1=CC=C(C(=O)OCCN(C)C)C=C1)[Si](C)(C)C	2371.2	Standard non polar	33892256
Tetracaine,1TMS,isomer #1	CCCCN(C1=CC=C(C(=O)OCCN(C)C)C=C1)[Si](C)(C)C	2549.8	Standard polar	33892256
Tetracaine,1TBDMS,isomer #1	CCCCN(C1=CC=C(C(=O)OCCN(C)C)C=C1)[Si](C)(C)C(C)(C)C	2458.7	Semi standard non polar	33892256
Tetracaine,1TBDMS,isomer #1	CCCCN(C1=CC=C(C(=O)OCCN(C)C)C=C1)[Si](C)(C)C(C)(C)C	2531.6	Standard non polar	33892256
Tetracaine,1TBDMS,isomer #1	CCCCN(C1=CC=C(C(=O)OCCN(C)C)C=C1)[Si](C)(C)C(C)(C)C	2667.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetracaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9410000000-44410ef7c8aa9cf69c00	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetracaine 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 - Tetracaine LC-ESI-QTOF , positive-QTOF	splash10-014i-0390000000-0435246ac53e48fff280	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-987e041aca4bd931c37e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine LC-ESI-QTOF , positive-QTOF	splash10-004i-2900000000-8fb0dc9fe24fa06781f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine LC-ESI-QTOF , positive-QTOF	splash10-00fu-8900000000-13f5e95cf7277be78720	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine LC-ESI-QTOF , positive-QTOF	splash10-0603-9500000000-43bdd69ad39be196db4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine LC-ESI-QFT , positive-QTOF	splash10-004i-2910000000-a6e7d7e502323aaae4e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 50V, Positive-QTOF	splash10-004i-0900000000-5675ccb86810d0c19921	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 40V, Positive-QTOF	splash10-004i-0900000000-f667e0561040fde13a6e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 10V, Positive-QTOF	splash10-014i-0390000000-0435246ac53e48fff280	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 35V, Positive-QTOF	splash10-004i-2910000000-177a9f94ee33c5e3a780	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 20V, Positive-QTOF	splash10-004i-0900000000-987e041aca4bd931c37e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 40V, Positive-QTOF	splash10-00fu-8900000000-13f5e95cf7277be78720	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 30V, Positive-QTOF	splash10-004i-2900000000-8fb0dc9fe24fa06781f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 20V, Positive-QTOF	splash10-004i-0910000000-c624685ddc6305978e32	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 40V, Positive-QTOF	splash10-00fu-8900000000-ab562b5fcc5f5c6a4d70	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 30V, Positive-QTOF	splash10-004i-0910000000-631df0fd7a7f46746624	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 10V, Positive-QTOF	splash10-016r-0790000000-7a0686e4023d6a08320a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 50V, Positive-QTOF	splash10-0603-9500000000-9bcd4ec45b8a7d946ab3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetracaine 50V, Positive-QTOF	splash10-0603-9500000000-43bdd69ad39be196db4d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetracaine 10V, Positive-QTOF	splash10-01b9-7590000000-79cdf8fa4b20ffd244d9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetracaine 20V, Positive-QTOF	splash10-05fr-9410000000-e21d86fb204c6a711827	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetracaine 40V, Positive-QTOF	splash10-0ab9-9300000000-dd6c4dcfde5f9b041900	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetracaine 10V, Negative-QTOF	splash10-03di-3590000000-242f903a843b11683464	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetracaine 20V, Negative-QTOF	splash10-08mm-5970000000-e8f29f21a99f222fb98b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetracaine 40V, Negative-QTOF	splash10-006x-9500000000-5d93cf36654dd12a934d	2017-07-26	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

DB09085

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5218

KEGG Compound ID

C07526

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetracaine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9468

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1362641

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 Tetracaine (HMDB0258868)

MOL for HMDB0258868 (Tetracaine)

3D MOL for HMDB0258868 (Tetracaine)

3D SDF for HMDB0258868 (Tetracaine)

3D-SDF for HMDB0258868 (Tetracaine)

PDB for HMDB0258868 (Tetracaine)

3D PDB for HMDB0258868 (Tetracaine)

SMILES for HMDB0258868 (Tetracaine)

INCHI for HMDB0258868 (Tetracaine)

Structure for HMDB0258868 (Tetracaine)

3D Structure for HMDB0258868 (Tetracaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra