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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:24:33 UTC

Update Date

2021-09-26 22:55:26 UTC

HMDB ID

HMDB0246385

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Chloro-3-ethoxy-7-guanidinoisocoumarin

Description

4-Chloro-3-ethoxy-7-guanidinoisocoumarin, also known as CEGIC, belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Based on a literature review a small amount of articles have been published on 4-Chloro-3-ethoxy-7-guanidinoisocoumarin. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-chloro-3-ethoxy-7-guanidinoisocoumarin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Chloro-3-ethoxy-7-guanidinoisocoumarin 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

HMDB0246385
     RDKit          3D
4-Chloro-3-ethoxy-7-guanidinoisocoumarin
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9526    0.6091   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9599   -0.8480   -0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101   -1.6221    0.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -1.3324   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -1.8044   -1.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534   -1.5786   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0894   -2.0667   -2.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074   -0.8233   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -0.6263   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2058    0.1164    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733    0.4393    0.0937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    0.8266   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6378   -0.0949   -0.3940 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9981    2.2250   -0.0289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102    0.6020    1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1710    0.4085    1.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -0.3156    0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941   -0.5650    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7509    0.0758    2.3419 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6615    1.1424   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634    0.7430    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9632    1.0896   -0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9772   -0.9182   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9020   -1.3439   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610   -0.9926   -1.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9656   -0.1617   -1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0376   -0.6434    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702    2.6928   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8447    2.7828    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922    1.1782    2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    0.8058    2.5521 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18  4  2  0
 17  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  9 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
M  END


  Mrv1652309112101242D          

 19 20  0  0  0  0            999 V2000
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   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
    0.0000   -1.6500    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
    0.7145   -0.4125    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.8579   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   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    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 Cl  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  2  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
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  4 18  1  0  0  0  0
  5 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246385

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC1=C(Cl)C2=C(C=C(C=C2)N=C(N)N)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H12ClN3O3/c1-2-18-11-9(13)7-4-3-6(16-12(14)15)5-8(7)10(17)19-11/h3-5H,2H2,1H3,(H4,14,15,16)

> <INCHI_KEY>
YFGMFEAGVQMIFH-UHFFFAOYSA-N

> <FORMULA>
C12H12ClN3O3

> <MOLECULAR_WEIGHT>
281.7

> <EXACT_MASS>
281.056719

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.494867465202766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N''-(4-chloro-3-ethoxy-1-oxo-1H-isochromen-7-yl)guanidine

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.418749232

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.368316362673255

> <JCHEM_POLAR_SURFACE_AREA>
99.92999999999999

> <JCHEM_REFRACTIVITY>
83.05489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N''-(4-chloro-3-ethoxy-1-oxoisochromen-7-yl)guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246385
     RDKit          3D
4-Chloro-3-ethoxy-7-guanidinoisocoumarin
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9526    0.6091   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9599   -0.8480   -0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101   -1.6221    0.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -1.3324   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -1.8044   -1.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534   -1.5786   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0894   -2.0667   -2.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074   -0.8233   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -0.6263   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2058    0.1164    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733    0.4393    0.0937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    0.8266   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6378   -0.0949   -0.3940 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9981    2.2250   -0.0289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102    0.6020    1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1710    0.4085    1.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -0.3156    0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941   -0.5650    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7509    0.0758    2.3419 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6615    1.1424   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634    0.7430    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9632    1.0896   -0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9772   -0.9182   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9020   -1.3439   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610   -0.9926   -1.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9656   -0.1617   -1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0376   -0.6434    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702    2.6928   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8447    2.7828    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922    1.1782    2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    0.8058    2.5521 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18  4  2  0
 17  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  9 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335  -0.000   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       8.002  -0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   19 Cl   UNK     0       0.000  -4.620   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    4                                                       
CONECT   19    5                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0246385
HETATM    1  C1  UNL     1       4.953   0.609  -0.037  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.960  -0.848  -0.408  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.910  -1.622   0.146  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.561  -1.332  -0.013  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.924  -1.804  -1.059  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.653  -1.579  -1.263  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.089  -2.067  -2.294  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.107  -0.823  -0.386  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.444  -0.626  -0.611  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.206   0.116   0.329  1.00  0.00           C  
HETATM   11  N1  UNL     1      -3.473   0.439   0.094  1.00  0.00           N  
HETATM   12  C8  UNL     1      -4.560   0.827  -0.101  1.00  0.00           C  
HETATM   13  N2  UNL     1      -5.638  -0.095  -0.394  1.00  0.00           N  
HETATM   14  N3  UNL     1      -4.998   2.225  -0.029  1.00  0.00           N  
HETATM   15  C9  UNL     1      -1.510   0.602   1.438  1.00  0.00           C  
HETATM   16  C10 UNL     1      -0.171   0.408   1.665  1.00  0.00           C  
HETATM   17  C11 UNL     1       0.555  -0.316   0.739  1.00  0.00           C  
HETATM   18  C12 UNL     1       1.894  -0.565   0.930  1.00  0.00           C  
HETATM   19 CL1  UNL     1       2.751   0.076   2.342  1.00  0.00          CL  
HETATM   20  H1  UNL     1       5.661   1.142  -0.745  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.363   0.743   0.951  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.963   1.090  -0.225  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.977  -0.918  -1.529  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.902  -1.344  -0.036  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.961  -0.993  -1.462  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.966  -0.162  -1.372  1.00  0.00           H  
HETATM   27  H8  UNL     1      -6.038  -0.643   0.372  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.470   2.693  -0.807  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.845   2.783   0.835  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.092   1.178   2.184  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.361   0.806   2.552  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4
CONECT    4    5   18   18
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9    9   17
CONECT    9   10   25
CONECT   10   11   15   15
CONECT   11   12   12
CONECT   12   13   14
CONECT   13   26   27
CONECT   14   28   29
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18
CONECT   18   19
END

HMDB0246385
     RDKit          3D
4-Chloro-3-ethoxy-7-guanidinoisocoumarin
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.9526    0.6091   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9599   -0.8480   -0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101   -1.6221    0.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -1.3324   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9236   -1.8044   -1.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534   -1.5786   -1.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0894   -2.0667   -2.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1074   -0.8233   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -0.6263   -0.6108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2058    0.1164    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4733    0.4393    0.0937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5600    0.8266   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6378   -0.0949   -0.3940 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9981    2.2250   -0.0289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5102    0.6020    1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1710    0.4085    1.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554   -0.3156    0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941   -0.5650    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7509    0.0758    2.3419 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6615    1.1424   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634    0.7430    0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9632    1.0896   -0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9772   -0.9182   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9020   -1.3439   -0.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9610   -0.9926   -1.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9656   -0.1617   -1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0376   -0.6434    0.3719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4702    2.6928   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8447    2.7828    0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922    1.1782    2.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610    0.8058    2.5521 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18  4  2  0
 17  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  9 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CEGIC	MeSH

Chemical Formula

C₁₂H₁₂ClN₃O₃

Average Molecular Weight

281.7

Monoisotopic Molecular Weight

281.056719

IUPAC Name

N''-(4-chloro-3-ethoxy-1-oxo-1H-isochromen-7-yl)guanidine

Traditional Name

N''-(4-chloro-3-ethoxy-1-oxoisochromen-7-yl)guanidine

CAS Registry Number

Not Available

SMILES

CCOC1=C(Cl)C2=C(C=C(C=C2)N=C(N)N)C(=O)O1

InChI Identifier

InChI=1S/C12H12ClN3O3/c1-2-18-11-9(13)7-4-3-6(16-12(14)15)5-8(7)10(17)19-11/h3-5H,2H2,1H3,(H4,14,15,16)

InChI Key

YFGMFEAGVQMIFH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
2-benzopyran
Alkyl aryl ether
Pyranone
Aryl chloride
Aryl halide
Pyran
Benzenoid
Heteroaromatic compound
Guanidine
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.52	ALOGPS
logP	1.42	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	9.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.05 m³·mol⁻¹	ChemAxon
Polarizability	27.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	167.571	30932474
DeepCCS	[M-H]-	165.213	30932474
DeepCCS	[M-2H]-	198.099	30932474
DeepCCS	[M+Na]+	173.664	30932474
AllCCS	[M+H]+	159.8	32859911
AllCCS	[M+H-H2O]+	156.3	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.0	32859911
AllCCS	[M-H]-	162.1	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-3-ethoxy-7-guanidinoisocoumarin	CCOC1=C(Cl)C2=C(C=C(C=C2)N=C(N)N)C(=O)O1	3368.8	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin	CCOC1=C(Cl)C2=C(C=C(C=C2)N=C(N)N)C(=O)O1	2528.6	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin	CCOC1=C(Cl)C2=C(C=C(C=C2)N=C(N)N)C(=O)O1	2801.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,1TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N)N[Si](C)(C)C)C=C2C(=O)O1	2687.6	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,1TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N)N[Si](C)(C)C)C=C2C(=O)O1	2604.7	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,1TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N)N[Si](C)(C)C)C=C2C(=O)O1	4251.0	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C)N[Si](C)(C)C)C=C2C(=O)O1	2786.2	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C)N[Si](C)(C)C)C=C2C(=O)O1	2592.0	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C)N[Si](C)(C)C)C=C2C(=O)O1	3862.1	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TMS,isomer #2	CCOC1=C(Cl)C2=CC=C(N=C(N)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	2701.3	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TMS,isomer #2	CCOC1=C(Cl)C2=CC=C(N=C(N)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	2693.0	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TMS,isomer #2	CCOC1=C(Cl)C2=CC=C(N=C(N)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	3986.3	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,3TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	2703.0	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,3TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	2683.7	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,3TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	3452.4	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,4TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	2782.6	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,4TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	2809.9	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,4TMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C=C2C(=O)O1	3103.7	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,1TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N)N[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	2920.3	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,1TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N)N[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	2772.9	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,1TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N)N[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	4205.2	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3145.1	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	2903.5	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3713.0	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TBDMS,isomer #2	CCOC1=C(Cl)C2=CC=C(N=C(N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3131.9	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TBDMS,isomer #2	CCOC1=C(Cl)C2=CC=C(N=C(N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3016.3	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,2TBDMS,isomer #2	CCOC1=C(Cl)C2=CC=C(N=C(N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3963.5	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,3TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3314.7	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,3TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3197.0	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,3TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3506.1	Standard polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,4TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3574.9	Semi standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,4TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3479.3	Standard non polar	33892256
4-Chloro-3-ethoxy-7-guanidinoisocoumarin,4TBDMS,isomer #1	CCOC1=C(Cl)C2=CC=C(N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2C(=O)O1	3329.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-0390000000-53f687d4b2ce7b11a678	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin 10V, Positive-QTOF	splash10-001i-0090000000-803e317d24e32e406b8c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin 20V, Positive-QTOF	splash10-0f80-0090000000-5f9fa211fea18f076a27	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin 40V, Positive-QTOF	splash10-059i-1790000000-706fd8602d5938bcf1b5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin 10V, Negative-QTOF	splash10-000i-0290000000-b8ec5a29a11e30a4e600	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin 20V, Negative-QTOF	splash10-000i-1090000000-01d2719c3f2d24fd095d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3-ethoxy-7-guanidinoisocoumarin 40V, Negative-QTOF	splash10-00lu-7970000000-d43984dd3c15c72ab2bb	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

170379

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

196678

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 4-Chloro-3-ethoxy-7-guanidinoisocoumarin (HMDB0246385)

MOL for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

3D MOL for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

3D SDF for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

3D-SDF for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

PDB for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

3D PDB for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

SMILES for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

INCHI for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

Structure for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

3D Structure for HMDB0246385 (4-Chloro-3-ethoxy-7-guanidinoisocoumarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra