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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:47:59 UTC

Update Date

2021-09-26 22:52:33 UTC

HMDB ID

HMDB0244654

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Coumarin-3-carboxylic acid succinimidyl ester

Description

Coumarin-3-carboxylic acid succinimidyl ester, also known as secca ester or succinimidyl coumarin-3-carboxylate, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Based on a literature review very few articles have been published on Coumarin-3-carboxylic acid succinimidyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). Coumarin-3-carboxylic acid succinimidyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Coumarin-3-carboxylic acid succinimidyl ester 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

HMDB0244654
     RDKit          3D
Coumarin-3-carboxylic acid succinimidyl ester
 30 32  0  0  0  0  0  0  0  0999 V2000
    1.3243    1.5421    0.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448    0.6350    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5564   -0.2718   -0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -0.2030   -0.5221 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112   -1.2945   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982   -2.4792    0.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048   -0.7694    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    0.7181    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055    0.9036   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    1.7979   -1.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    0.6213    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295   -0.4504   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -0.3923   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5019   -1.4836   -0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -1.4609   -0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5437   -0.3524   -0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141    0.7298    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4360    0.7326    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7169    1.7423    0.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176    1.7120    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395    2.7047    0.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7427   -0.9745   -0.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7114   -1.1834    0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.9145    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8320    1.3450   -0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3247   -0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886   -2.3518   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3970   -2.3323   -1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6243   -0.3595   -0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3579    1.5844    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 20 11  1  0
 18 13  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END


  Mrv1652309102123482D          

 21 23  0  0  0  0            999 V2000
   -2.7346    0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221    0.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152    0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9021    1.3725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1826   -0.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3541   -1.1425    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    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 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
    2.8579    0.0000    0.0000 C   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244654

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(ON1C(=O)CCC1=O)C1=CC2=CC=CC=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H9NO6/c16-11-5-6-12(17)15(11)21-14(19)9-7-8-3-1-2-4-10(8)20-13(9)18/h1-4,7H,5-6H2

> <INCHI_KEY>
NTXGVUJAUMMHQO-UHFFFAOYSA-N

> <FORMULA>
C14H9NO6

> <MOLECULAR_WEIGHT>
287.227

> <EXACT_MASS>
287.042987014

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.539243297166422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dioxopyrrolidin-1-yl 2-oxo-2H-chromene-3-carboxylate

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
0.9735214256666667

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.696003910171896

> <JCHEM_PKA_STRONGEST_BASIC>
-7.129734900778146

> <JCHEM_POLAR_SURFACE_AREA>
89.97999999999999

> <JCHEM_REFRACTIVITY>
68.17670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dioxopyrrolidin-1-yl 2-oxochromene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244654
     RDKit          3D
Coumarin-3-carboxylic acid succinimidyl ester
 30 32  0  0  0  0  0  0  0  0999 V2000
    1.3243    1.5421    0.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448    0.6350    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5564   -0.2718   -0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -0.2030   -0.5221 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112   -1.2945   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982   -2.4792    0.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048   -0.7694    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    0.7181    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055    0.9036   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    1.7979   -1.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    0.6213    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295   -0.4504   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -0.3923   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5019   -1.4836   -0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -1.4609   -0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5437   -0.3524   -0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141    0.7298    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4360    0.7326    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7169    1.7423    0.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176    1.7120    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395    2.7047    0.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7427   -0.9745   -0.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7114   -1.1834    0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.9145    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8320    1.3450   -0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3247   -0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886   -2.3518   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3970   -2.3323   -1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6243   -0.3595   -0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3579    1.5844    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 20 11  1  0
 18 13  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0      -5.105   0.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.335   1.852   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.828   1.532   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.684   2.562   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -2.667   0.000   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -4.074  -0.626   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.394  -2.133   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   11   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0244654
HETATM    1  O1  UNL     1       1.324   1.542   0.741  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.745   0.635   0.062  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.556  -0.272  -0.598  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.946  -0.203  -0.522  1.00  0.00           N  
HETATM    5  C2  UNL     1       3.811  -1.295  -0.146  1.00  0.00           C  
HETATM    6  O3  UNL     1       3.498  -2.479   0.029  1.00  0.00           O  
HETATM    7  C3  UNL     1       5.205  -0.769   0.009  1.00  0.00           C  
HETATM    8  C4  UNL     1       4.965   0.718   0.148  1.00  0.00           C  
HETATM    9  C5  UNL     1       3.805   0.904  -0.780  1.00  0.00           C  
HETATM   10  O4  UNL     1       3.588   1.798  -1.608  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.715   0.621   0.028  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.430  -0.450  -0.432  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.812  -0.392  -0.383  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.502  -1.484  -0.844  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.887  -1.461  -0.804  1.00  0.00           C  
HETATM   16  C11 UNL     1      -5.544  -0.352  -0.309  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.814   0.730   0.146  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.436   0.733   0.119  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.717   1.742   0.550  1.00  0.00           O  
HETATM   20  C14 UNL     1      -1.418   1.712   0.517  1.00  0.00           C  
HETATM   21  O6  UNL     1      -0.739   2.705   0.941  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.743  -0.974  -0.921  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.711  -1.183   0.904  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.564   0.915   1.171  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.832   1.345  -0.113  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.913  -1.325  -0.823  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.989  -2.352  -1.230  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.397  -2.332  -1.174  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.624  -0.359  -0.294  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.358   1.584   0.528  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4
CONECT    4    5    9
CONECT    5    6    6    7
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   10
CONECT   11   12   12   20
CONECT   12   13   26
CONECT   13   14   14   18
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19
CONECT   19   20
CONECT   20   21   21
END

HMDB0244654
     RDKit          3D
Coumarin-3-carboxylic acid succinimidyl ester
 30 32  0  0  0  0  0  0  0  0999 V2000
    1.3243    1.5421    0.7409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448    0.6350    0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5564   -0.2718   -0.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -0.2030   -0.5221 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112   -1.2945   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982   -2.4792    0.0285 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048   -0.7694    0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    0.7181    0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055    0.9036   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    1.7979   -1.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    0.6213    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295   -0.4504   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8120   -0.3923   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5019   -1.4836   -0.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -1.4609   -0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5437   -0.3524   -0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141    0.7298    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4360    0.7326    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7169    1.7423    0.5501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176    1.7120    0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7395    2.7047    0.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7427   -0.9745   -0.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7114   -1.1834    0.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5644    0.9145    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8320    1.3450   -0.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126   -1.3247   -0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9886   -2.3518   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3970   -2.3323   -1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6243   -0.3595   -0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3579    1.5844    0.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
  9  4  1  0
 20 11  1  0
 18 13  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Coumarin-3-carboxylate succinimidyl ester	Generator
SECCA ester	HMDB
Succinimidyl coumarin-3-carboxylate	HMDB

Chemical Formula

C₁₄H₉NO₆

Average Molecular Weight

287.227

Monoisotopic Molecular Weight

287.042987014

IUPAC Name

2,5-dioxopyrrolidin-1-yl 2-oxo-2H-chromene-3-carboxylate

Traditional Name

2,5-dioxopyrrolidin-1-yl 2-oxochromene-3-carboxylate

CAS Registry Number

Not Available

SMILES

O=C(ON1C(=O)CCC1=O)C1=CC2=CC=CC=C2OC1=O

InChI Identifier

InChI=1S/C14H9NO6/c16-11-5-6-12(17)15(11)21-14(19)9-7-8-3-1-2-4-10(8)20-13(9)18/h1-4,7H,5-6H2

InChI Key

NTXGVUJAUMMHQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Pyranone
Pyran
Pyrrolidone
2-pyrrolidone
Benzenoid
Dicarboximide
Heteroaromatic compound
Pyrrolidine
Carboxylic acid salt
Lactam
Lactone
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic salt
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)

Source

Exogenous

Exogenous (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	1.31	ALOGPS
logP	0.97	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	17.7	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.18 m³·mol⁻¹	ChemAxon
Polarizability	26.54 Å³	ChemAxon
Number of Rings	3	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]+	160.503	30932474
DeepCCS	[M-H]-	158.107	30932474
DeepCCS	[M-2H]-	191.062	30932474
DeepCCS	[M+Na]+	166.53	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.4	32859911
AllCCS	[M+NH4]+	166.4	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	164.2	32859911
AllCCS	[M+Na-2H]-	163.5	32859911
AllCCS	[M+HCOO]-	162.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coumarin-3-carboxylic acid succinimidyl ester	O=C(ON1C(=O)CCC1=O)C1=CC2=CC=CC=C2OC1=O	3786.4	Standard polar	33892256
Coumarin-3-carboxylic acid succinimidyl ester	O=C(ON1C(=O)CCC1=O)C1=CC2=CC=CC=C2OC1=O	2563.9	Standard non polar	33892256
Coumarin-3-carboxylic acid succinimidyl ester	O=C(ON1C(=O)CCC1=O)C1=CC2=CC=CC=C2OC1=O	2674.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Coumarin-3-carboxylic acid succinimidyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-8920000000-5a9951cbf8127f8cfbdc	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumarin-3-carboxylic acid succinimidyl ester 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 - Coumarin-3-carboxylic acid succinimidyl ester 10V, Positive-QTOF	splash10-000i-0590000000-00ec1f3138637b225796	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-3-carboxylic acid succinimidyl ester 20V, Positive-QTOF	splash10-00di-0900000000-cacb66a1a01e330ab428	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-3-carboxylic acid succinimidyl ester 40V, Positive-QTOF	splash10-0ab9-1920000000-708fce0b689f88b4032b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-3-carboxylic acid succinimidyl ester 10V, Negative-QTOF	splash10-000j-1930000000-44f9110ab3ee17e81c1c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-3-carboxylic acid succinimidyl ester 20V, Negative-QTOF	splash10-0002-2930000000-a71dd342f63e66797451	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumarin-3-carboxylic acid succinimidyl ester 40V, Negative-QTOF	splash10-0002-1900000000-0fb31d780c089f570c5f	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

113268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127679

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 Coumarin-3-carboxylic acid succinimidyl ester (HMDB0244654)

MOL for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

3D MOL for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

3D SDF for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

3D-SDF for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

PDB for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

3D PDB for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

SMILES for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

INCHI for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

Structure for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

3D Structure for HMDB0244654 (Coumarin-3-carboxylic acid succinimidyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra