Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:29:59 UTC

Update Date

2021-09-26 22:59:37 UTC

HMDB ID

HMDB0249019

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester

Description

Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Based on a literature review a small amount of articles have been published on Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl 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

HMDB0249019
     RDKit          3D
Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester
 37 38  0  0  0  0  0  0  0  0999 V2000
    1.0947    3.1969   -0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    1.9437   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7548    2.0512    1.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0811    0.6886   -0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.4275    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -1.0737    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391   -0.5473   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8380   -1.2637   -0.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591   -1.4056    0.5632 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.4161   -0.6384    1.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879   -2.4017    0.6997 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7616   -2.1712    0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234   -2.6609    1.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4951   -2.0314    1.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102   -0.9198    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -0.2754    0.9120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168   -0.6358    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6569   -1.5730   -0.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.0279   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    1.0586    0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591    1.6665    0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154    1.2515   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.2345   -0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561   -0.3794   -0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    3.8638   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    3.6641   -0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9501    3.0341   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8868    0.5166   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.5346   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769   -2.7065    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760   -3.5201    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -2.3668    2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169    1.4221    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0543    2.4829    1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6904    1.7129   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1366   -0.1013   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9774   -1.1818   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 15  5  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  7 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 23 36  1  0
 24 37  1  0
M  CHG  2   9   1  11  -1
M  END


  Mrv1652309112105302D          

 24 25  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 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
    1.4289   -1.6500    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   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
   -2.1434   -2.8875    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
   -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 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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  CHG  2  22   1  24  -1
M  END
> <DATABASE_ID>
HMDB0249019

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1=C(CO[N+]([O-])=O)C=CC=C1OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13NO7/c1-11(18)23-15-13(10-22-17(20)21)8-5-9-14(15)24-16(19)12-6-3-2-4-7-12/h2-9H,10H2,1H3

> <INCHI_KEY>
LQGDSTMEWBGZPH-UHFFFAOYSA-N

> <FORMULA>
C16H13NO7

> <MOLECULAR_WEIGHT>
331.28

> <EXACT_MASS>
331.069201763

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.38524739385415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl benzoate

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
3.173107077

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.009359434888056

> <JCHEM_POLAR_SURFACE_AREA>
104.97

> <JCHEM_REFRACTIVITY>
81.49900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249019
     RDKit          3D
Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester
 37 38  0  0  0  0  0  0  0  0999 V2000
    1.0947    3.1969   -0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    1.9437   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7548    2.0512    1.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0811    0.6886   -0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.4275    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -1.0737    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391   -0.5473   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8380   -1.2637   -0.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591   -1.4056    0.5632 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.4161   -0.6384    1.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879   -2.4017    0.6997 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7616   -2.1712    0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234   -2.6609    1.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4951   -2.0314    1.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102   -0.9198    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -0.2754    0.9120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168   -0.6358    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6569   -1.5730   -0.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.0279   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    1.0586    0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591    1.6665    0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154    1.2515   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.2345   -0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561   -0.3794   -0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    3.8638   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    3.6641   -0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9501    3.0341   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8868    0.5166   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.5346   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769   -2.7065    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760   -3.5201    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -2.3668    2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169    1.4221    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0543    2.4829    1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6904    1.7129   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1366   -0.1013   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9774   -1.1818   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 15  5  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  7 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 23 36  1  0
 24 37  1  0
M  CHG  2   9   1  11  -1
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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -5.390   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  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  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+1
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    6   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0249019
HETATM    1  C1  UNL     1       1.095   3.197  -0.898  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.319   1.944  -0.141  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.755   2.051   1.037  1.00  0.00           O  
HETATM    4  O2  UNL     1       1.081   0.689  -0.646  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.322  -0.428   0.141  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.571  -1.074   0.156  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.639  -0.547  -0.695  1.00  0.00           C  
HETATM    8  O3  UNL     1       4.838  -1.264  -0.587  1.00  0.00           O  
HETATM    9  N1  UNL     1       5.559  -1.406   0.563  1.00  0.00           N1+
HETATM   10  O4  UNL     1       5.416  -0.638   1.557  1.00  0.00           O  
HETATM   11  O5  UNL     1       6.488  -2.402   0.700  1.00  0.00           O1-
HETATM   12  C6  UNL     1       2.762  -2.171   0.948  1.00  0.00           C  
HETATM   13  C7  UNL     1       1.723  -2.661   1.749  1.00  0.00           C  
HETATM   14  C8  UNL     1       0.495  -2.031   1.739  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.310  -0.920   0.933  1.00  0.00           C  
HETATM   16  O6  UNL     1      -0.918  -0.275   0.912  1.00  0.00           O  
HETATM   17  C10 UNL     1      -1.917  -0.636   0.017  1.00  0.00           C  
HETATM   18  O7  UNL     1      -1.657  -1.573  -0.773  1.00  0.00           O  
HETATM   19  C11 UNL     1      -3.213   0.028  -0.022  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.517   1.059   0.838  1.00  0.00           C  
HETATM   21  C13 UNL     1      -4.759   1.667   0.772  1.00  0.00           C  
HETATM   22  C14 UNL     1      -5.715   1.251  -0.156  1.00  0.00           C  
HETATM   23  C15 UNL     1      -5.404   0.234  -0.998  1.00  0.00           C  
HETATM   24  C16 UNL     1      -4.156  -0.379  -0.934  1.00  0.00           C  
HETATM   25  H1  UNL     1       1.969   3.864  -0.686  1.00  0.00           H  
HETATM   26  H2  UNL     1       0.178   3.664  -0.480  1.00  0.00           H  
HETATM   27  H3  UNL     1       0.950   3.034  -1.973  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.887   0.517  -0.460  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.361  -0.535  -1.776  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.677  -2.706   1.002  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.876  -3.520   2.368  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.340  -2.367   2.337  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.817   1.422   1.576  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.054   2.483   1.423  1.00  0.00           H  
HETATM   35  H11 UNL     1      -6.690   1.713  -0.223  1.00  0.00           H  
HETATM   36  H12 UNL     1      -6.137  -0.101  -1.726  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.977  -1.182  -1.635  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6   15
CONECT    6    7   12
CONECT    7    8   28   29
CONECT    8    9
CONECT    9   10   10   11
CONECT   12   13   13   30
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   20   20   24
CONECT   20   21   33
CONECT   21   22   22   34
CONECT   22   23   35
CONECT   23   24   24   36
CONECT   24   37
END

HMDB0249019
     RDKit          3D
Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester
 37 38  0  0  0  0  0  0  0  0999 V2000
    1.0947    3.1969   -0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    1.9437   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7548    2.0512    1.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0811    0.6886   -0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.4275    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -1.0737    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391   -0.5473   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8380   -1.2637   -0.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5591   -1.4056    0.5632 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.4161   -0.6384    1.5573 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4879   -2.4017    0.6997 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.7616   -2.1712    0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234   -2.6609    1.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4951   -2.0314    1.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102   -0.9198    0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9180   -0.2754    0.9120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168   -0.6358    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6569   -1.5730   -0.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    0.0279   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    1.0586    0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591    1.6665    0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7154    1.2515   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.2345   -0.9977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561   -0.3794   -0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9694    3.8638   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    3.6641   -0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9501    3.0341   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8868    0.5166   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615   -0.5346   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6769   -2.7065    1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760   -3.5201    2.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397   -2.3668    2.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169    1.4221    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0543    2.4829    1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6904    1.7129   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1366   -0.1013   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9774   -1.1818   -1.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 15  5  1  0
 24 19  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  7 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 23 36  1  0
 24 37  1  0
M  CHG  2   9   1  11  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Benzoate 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester	Generator

Chemical Formula

C₁₆H₁₃NO₇

Average Molecular Weight

331.28

Monoisotopic Molecular Weight

331.069201763

IUPAC Name

2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl benzoate

Traditional Name

2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1=C(CO[N+]([O-])=O)C=CC=C1OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H13NO7/c1-11(18)23-15-13(10-22-17(20)21)8-5-9-14(15)24-16(19)12-6-3-2-4-7-12/h2-9H,10H2,1H3

InChI Key

LQGDSTMEWBGZPH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
Phenol ester
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alkyl nitrate
Organic nitrate
Organic nitro compound
Organic nitric acid or derivatives
Carboxylic acid ester
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	2.86	ALOGPS
logP	3.17	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	81.5 m³·mol⁻¹	ChemAxon
Polarizability	31.39 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]+	151.127	30932474
DeepCCS	[M-H]-	148.835	30932474
DeepCCS	[M-2H]-	183.112	30932474
DeepCCS	[M+Na]+	158.869	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.2074 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2208.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	390.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	560.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	587.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1240.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	481.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1521.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	420.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	314.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	277.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	74.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester	CC(=O)OC1=C(CO[N+]([O-])=O)C=CC=C1OC(=O)C1=CC=CC=C1	3679.7	Standard polar	33892256
Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester	CC(=O)OC1=C(CO[N+]([O-])=O)C=CC=C1OC(=O)C1=CC=CC=C1	2464.5	Standard non polar	33892256
Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester	CC(=O)OC1=C(CO[N+]([O-])=O)C=CC=C1OC(=O)C1=CC=CC=C1	2391.3	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 - Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1920000000-dbf38b5607ce1fbafe8f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90752661

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 Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester (HMDB0249019)

MOL for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

3D MOL for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

3D SDF for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

3D-SDF for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

PDB for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

3D PDB for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

SMILES for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

INCHI for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

Structure for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

3D Structure for HMDB0249019 (Benzoic acid 2-(acetyloxy)-3-[(nitrooxy)methyl]phenyl ester)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra