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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:03:34 UTC

Update Date

2021-09-26 22:59:00 UTC

HMDB ID

HMDB0248628

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Articaine

Description

N-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid, also known as carticaine, belongs to the class of organic compounds known as thiophene carboxylic acids and derivatives. Thiophene carboxylic acids and derivatives are compounds containing a thiophene ring which bears a carboxylic acid group (or a salt/ester thereof). Based on a literature review very few articles have been published on N-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Articaine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Articaine 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

HMDB0248628
     RDKit          3D
Articaine
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.0998   -1.2294   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891   -0.6640   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2955    0.0555    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    0.7073    0.7013 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.0439    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5863   -0.8155   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696    0.8011    1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    1.2157    2.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2899    1.1671    0.6409 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387    1.0419   -0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    1.6914   -1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    2.6419   -1.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973    1.4819   -2.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956    0.3938   -2.3725 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637    0.2159   -0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672   -0.5975    0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957   -0.5964    1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688   -1.3669    0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4153   -2.1802    1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136   -0.4612   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -1.3832    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370   -2.1772   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686   -1.5411   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267    0.0359   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0978    0.8320    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3694   -0.6737    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334    1.4610   -0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -0.8296    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587   -1.8936   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352   -0.3616   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726   -0.8223   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960    0.4584    3.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526    2.6538   -0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698    3.6761   -2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979    2.3799   -2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    1.9417   -3.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7826   -3.0740    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -2.4716    1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2583   -1.6696    1.5030 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
  5  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 15 10  2  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
  5 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END


  Mrv0541 06201410472D          

 19 19  0  0  0  0            999 V2000
    3.1406   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6150    0.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9984   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4648   -1.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0351    0.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2281    0.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9984   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1418   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8955   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0671   -1.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840   -0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4274   -1.0164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129    0.2210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4540   -2.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8517   -2.0014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4476   -0.3264    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  8  2  1  0  0  0  0
  8  7  2  0  0  0  0
  9  3  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  4  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18  4  1  0  0  0  0
 18 13  1  0  0  0  0
 19  7  1  0  0  0  0
 19 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248628

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C13H20N2O3S/c1-5-6-14-9(3)12(16)15-10-8(2)7-19-11(10)13(17)18-4/h7,9,14H,5-6H2,1-4H3,(H,15,16)

> <INCHI_KEY>
QTGIAADRBBLJGA-UHFFFAOYSA-N

> <FORMULA>
C13H20N2O3S

> <MOLECULAR_WEIGHT>
284.374

> <EXACT_MASS>
284.119463206

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.800813059088995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
0.9551475814068912

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.420687824194913

> <JCHEM_PKA_STRONGEST_BASIC>
8.91146087608256

> <JCHEM_POLAR_SURFACE_AREA>
70.92

> <JCHEM_REFRACTIVITY>
77.5333

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carticaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248628
     RDKit          3D
Articaine
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.0998   -1.2294   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891   -0.6640   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2955    0.0555    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    0.7073    0.7013 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.0439    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5863   -0.8155   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696    0.8011    1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    1.2157    2.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2899    1.1671    0.6409 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387    1.0419   -0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    1.6914   -1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    2.6419   -1.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973    1.4819   -2.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956    0.3938   -2.3725 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637    0.2159   -0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672   -0.5975    0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957   -0.5964    1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688   -1.3669    0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4153   -2.1802    1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136   -0.4612   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -1.3832    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370   -2.1772   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686   -1.5411   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267    0.0359   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0978    0.8320    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3694   -0.6737    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334    1.4610   -0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -0.8296    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587   -1.8936   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352   -0.3616   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726   -0.8223   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960    0.4584    3.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526    2.6538   -0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698    3.6761   -2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979    2.3799   -2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    1.9417   -3.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7826   -3.0740    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -2.4716    1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2583   -1.6696    1.5030 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
  5  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 15 10  2  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
  5 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 20-JUN-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-14         0                                  
HETATM    1  C   UNK     0       5.862  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.215   1.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.197  -3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.534  -2.705   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.196  -1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.530  -1.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.866   0.724   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.359   0.404   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.197  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.198  -1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.605  -1.754   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.531  -1.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.925  -3.260   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.863  -1.127   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      13.864  -1.897   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      12.531   0.413   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      15.781  -4.291   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      18.390  -3.736   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0      17.636  -0.609   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   18                                                            
CONECT    5    1    6                                                       
CONECT    6    5   14                                                       
CONECT    7    8   19                                                       
CONECT    8    2    7   10                                                  
CONECT    9    3   12   14                                                  
CONECT   10    8   11   15                                                  
CONECT   11   10   13   19                                                  
CONECT   12    9   15   16                                                  
CONECT   13   11   17   18                                                  
CONECT   14    6    9                                                       
CONECT   15   10   12                                                       
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18    4   13                                                       
CONECT   19    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0248628
HETATM    1  C1  UNL     1       5.100  -1.229  -0.344  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.689  -0.664  -0.601  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.296   0.056   0.660  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.063   0.707   0.701  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.854  -0.044   0.705  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.586  -0.816  -0.544  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.270   0.801   1.197  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.031   1.216   2.572  1.00  0.00           O  
HETATM    9  N2  UNL     1      -1.290   1.167   0.641  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.939   1.042  -0.609  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.565   1.691  -1.747  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.369   2.642  -1.779  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.297   1.482  -2.877  1.00  0.00           C  
HETATM   14  S1  UNL     1      -3.496   0.394  -2.372  1.00  0.00           S  
HETATM   15  C11 UNL     1      -3.064   0.216  -0.752  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.667  -0.597   0.330  1.00  0.00           C  
HETATM   17  O2  UNL     1      -3.196  -0.596   1.486  1.00  0.00           O  
HETATM   18  O3  UNL     1      -4.769  -1.367   0.045  1.00  0.00           O  
HETATM   19  C13 UNL     1      -5.415  -2.180   1.015  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.814  -0.461  -0.692  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.227  -1.383   0.727  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.237  -2.177  -0.932  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.069  -1.541  -0.830  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.727   0.036  -1.454  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.098   0.832   0.835  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.369  -0.674   1.522  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.033   1.461  -0.020  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.946  -0.830   1.562  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.859  -1.894  -0.401  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.135  -0.362  -1.399  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.473  -0.822  -0.858  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.096   0.458   3.241  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.153   2.654  -0.825  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.770   3.676  -2.005  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.298   2.380  -2.595  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.106   1.942  -3.867  1.00  0.00           H  
HETATM   37  H18 UNL     1      -5.783  -3.074   0.450  1.00  0.00           H  
HETATM   38  H19 UNL     1      -4.699  -2.472   1.809  1.00  0.00           H  
HETATM   39  H20 UNL     1      -6.258  -1.670   1.503  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
CONECT    5    6    7   28
CONECT    6   29   30   31
CONECT    7    8    9    9
CONECT    8   32
CONECT    9   10
CONECT   10   11   15   15
CONECT   11   12   13   13
CONECT   12   33   34   35
CONECT   13   14   36
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   37   38   39
END

HMDB0248628
     RDKit          3D
Articaine
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.0998   -1.2294   -0.3440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6891   -0.6640   -0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2955    0.0555    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    0.7073    0.7013 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.0439    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5863   -0.8155   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696    0.8011    1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    1.2157    2.5717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2899    1.1671    0.6409 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9387    1.0419   -0.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650    1.6914   -1.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    2.6419   -1.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973    1.4819   -2.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956    0.3938   -2.3725 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0637    0.2159   -0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672   -0.5975    0.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1957   -0.5964    1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688   -1.3669    0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4153   -2.1802    1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136   -0.4612   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -1.3832    0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2370   -2.1772   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0686   -1.5411   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267    0.0359   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0978    0.8320    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3694   -0.6737    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334    1.4610   -0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -0.8296    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8587   -1.8936   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1352   -0.3616   -1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726   -0.8223   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0960    0.4584    3.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526    2.6538   -0.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698    3.6761   -2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979    2.3799   -2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    1.9417   -3.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7826   -3.0740    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -2.4716    1.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2583   -1.6696    1.5030 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
  5  7  1  0
  7  8  1  0
  7  9  2  3
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 15 10  2  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
  5 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Carticaine	Kegg
N-[2-(Methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidate	Generator
Carticain	MeSH
Carticaine hydrochloride	MeSH
Hoe 045	MeSH
Articain	MeSH
Hoechst brand OF carticaine hydrochloride	MeSH
Hydrochloride, carticaine	MeSH
Ultracaine	MeSH
Hoe-045	MeSH

Chemical Formula

C₁₃H₂₀N₂O₃S

Average Molecular Weight

284.374

Monoisotopic Molecular Weight

284.119463206

IUPAC Name

N-[2-(methoxycarbonyl)-4-methylthiophen-3-yl]-2-(propylamino)propanimidic acid

Traditional Name

carticaine

CAS Registry Number

Not Available

SMILES

CCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC

InChI Identifier

InChI=1S/C13H20N2O3S/c1-5-6-14-9(3)12(16)15-10-8(2)7-19-11(10)13(17)18-4/h7,9,14H,5-6H2,1-4H3,(H,15,16)

InChI Key

QTGIAADRBBLJGA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiophene carboxylic acids and derivatives. Thiophene carboxylic acids and derivatives are compounds containing a thiophene ring which bears a carboxylic acid group (or a salt/ester thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiophenes

Sub Class

Thiophene carboxylic acids and derivatives

Direct Parent

Thiophene carboxylic acids and derivatives

Alternative Parents

Substituents

Thiophene carboxylic acid or derivatives
Methyl ester
Heteroaromatic compound
Amino acid or derivatives
Carboxylic acid ester
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Organic oxygen compound
Amine
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.9	ALOGPS
logP	0.96	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	77.53 m³·mol⁻¹	ChemAxon
Polarizability	30.8 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]+	163.619	30932474
DeepCCS	[M-H]-	161.261	30932474
DeepCCS	[M-2H]-	194.147	30932474
DeepCCS	[M+Na]+	169.712	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	168.2	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	169.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Articaine	CCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC	2786.9	Standard polar	33892256
Articaine	CCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC	2221.2	Standard non polar	33892256
Articaine	CCCNC(C)C(O)=NC1=C(SC=C1C)C(=O)OC	2144.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Articaine,2TMS,isomer #1	CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C)[Si](C)(C)C	2191.0	Semi standard non polar	33892256
Articaine,2TMS,isomer #1	CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C)[Si](C)(C)C	2166.1	Standard non polar	33892256
Articaine,2TMS,isomer #1	CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C)[Si](C)(C)C	2840.5	Standard polar	33892256
Articaine,2TBDMS,isomer #1	CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2627.8	Semi standard non polar	33892256
Articaine,2TBDMS,isomer #1	CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2503.3	Standard non polar	33892256
Articaine,2TBDMS,isomer #1	CCCN(C(C)C(=NC1=C(C(=O)OC)SC=C1C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2988.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Articaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g0-9710000000-17a712ab6964343fb8f4	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Articaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Articaine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Articaine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Articaine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Articaine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Articaine 10V, Positive-QTOF	splash10-000i-5190000000-2f877abe52116e1258b4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 20V, Positive-QTOF	splash10-000l-9000000000-0a18b19266dbc8f3bc9c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 40V, Positive-QTOF	splash10-0006-9100000000-91e2bdeec7aabd58a49d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 10V, Negative-QTOF	splash10-0f89-0190000000-8c22a5f16cbfcc830f1a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 20V, Negative-QTOF	splash10-0fl0-0590000000-3c5b853eac8c14c771b8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 40V, Negative-QTOF	splash10-0a6s-9720000000-ad595a95bd3d6a9368de	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 10V, Positive-QTOF	splash10-000i-0090000000-96d0ca67edf9c6365a45	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 20V, Positive-QTOF	splash10-059i-9440000000-17da9b566219ea11abbd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 40V, Positive-QTOF	splash10-0abc-9200000000-30cacb6ff9fab18becff	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 10V, Negative-QTOF	splash10-0udi-0190000000-ece2126e2377c42c05a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 20V, Negative-QTOF	splash10-02ji-2940000000-aaa8465919bcdabc7df9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Articaine 40V, Negative-QTOF	splash10-000i-5900000000-e1c427cc8b6e8e4ae1fb	2021-10-12	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

29837

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 Articaine (HMDB0248628)

MOL for HMDB0248628 (Articaine)

3D MOL for HMDB0248628 (Articaine)

3D SDF for HMDB0248628 (Articaine)

3D-SDF for HMDB0248628 (Articaine)

PDB for HMDB0248628 (Articaine)

3D PDB for HMDB0248628 (Articaine)

SMILES for HMDB0248628 (Articaine)

INCHI for HMDB0248628 (Articaine)

Structure for HMDB0248628 (Articaine)

3D Structure for HMDB0248628 (Articaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra