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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:25:58 UTC

Update Date

2021-09-26 23:10:39 UTC

HMDB ID

HMDB0255647

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nitrofenac

Description

Nitrofenac belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. Based on a literature review a significant number of articles have been published on Nitrofenac. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nitrofenac is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nitrofenac 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

  Mrv1652309112117262D          

 27 28  0  0  0  0            999 V2000
   -0.7145   -4.5375    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
   -1.4289   -3.3000    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   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 N   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
   -2.1434   -2.0625    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
   -2.8579   -0.8250    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
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
M  CHG  2  16   1  18  -1
M  END

HMDB0255647
     RDKit          3D
Nitrofenac
 45 46  0  0  0  0  0  0  0  0999 V2000
    0.4800   -1.6143    0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -1.8827   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4644   -2.3134   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.3912   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3076   -3.5906   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4961   -3.7063    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092   -2.5676    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039   -1.3401   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -1.2585   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    0.0063   -1.0905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6450    1.2250   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5342    1.7585   -1.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    0.9061   -3.2399 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    2.9459   -1.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798    3.6240   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0890    3.1074    0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303    1.9123    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    1.2554    1.4967 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -1.7525   -1.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739   -1.3618   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739   -0.0047   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4476    0.1619    0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    1.4816    1.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9271    1.4970    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4031    2.5882    2.4534 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.3812    2.5325    3.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568    3.7768    2.2946 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1947   -3.2986   -2.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -1.6277   -2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -4.4859   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8564   -4.7108    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1545   -2.6736    0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -0.4506    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    0.0652   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9089    3.3548   -2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4911    4.5593   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883    3.6229    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -2.1026    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394   -1.4160   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    0.7691   -0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.0986    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -0.6258    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2664   -0.0270   -0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    1.6779    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.2753    0.4194 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
  9  4  1  0
 17 11  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
M  CHG  2  25   1  27  -1
M  END

  Mrv1652309112117262D          

 27 28  0  0  0  0            999 V2000
   -0.7145   -4.5375    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
   -1.4289   -3.3000    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   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 N   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
   -2.1434   -2.0625    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
   -2.8579   -0.8250    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
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 27  1  0  0  0  0
M  CHG  2  16   1  18  -1
M  END
> <DATABASE_ID>
HMDB0255647

> <DATABASE_NAME>
hmdb

> <SMILES>
[O-][N+](=O)OCCCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C18H18Cl2N2O5/c19-14-7-5-8-15(20)18(14)21-16-9-2-1-6-13(16)12-17(23)26-10-3-4-11-27-22(24)25/h1-2,5-9,21H,3-4,10-12H2

> <INCHI_KEY>
CQVHWLHWUZRTQC-UHFFFAOYSA-N

> <FORMULA>
C18H18Cl2N2O5

> <MOLECULAR_WEIGHT>
413.25

> <EXACT_MASS>
412.0592771

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
40.18541021657314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(nitrooxy)butyl 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate

> <ALOGPS_LOGP>
5.23

> <JCHEM_LOGP>
4.990638328666666

> <ALOGPS_LOGS>
-6.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.401793177928838

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0760961974822187

> <JCHEM_POLAR_SURFACE_AREA>
90.7

> <JCHEM_REFRACTIVITY>
101.7226

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(nitrooxy)butyl {2-[(2,6-dichlorophenyl)amino]phenyl}acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255647
     RDKit          3D
Nitrofenac
 45 46  0  0  0  0  0  0  0  0999 V2000
    0.4800   -1.6143    0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -1.8827   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4644   -2.3134   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.3912   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3076   -3.5906   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4961   -3.7063    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092   -2.5676    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039   -1.3401   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -1.2585   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    0.0063   -1.0905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6450    1.2250   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5342    1.7585   -1.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    0.9061   -3.2399 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    2.9459   -1.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798    3.6240   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0890    3.1074    0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303    1.9123    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    1.2554    1.4967 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -1.7525   -1.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739   -1.3618   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739   -0.0047   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4476    0.1619    0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    1.4816    1.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9271    1.4970    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4031    2.5882    2.4534 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.3812    2.5325    3.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568    3.7768    2.2946 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1947   -3.2986   -2.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -1.6277   -2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -4.4859   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8564   -4.7108    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1545   -2.6736    0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -0.4506    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    0.0652   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9089    3.3548   -2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4911    4.5593   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883    3.6229    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -2.1026    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394   -1.4160   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    0.7691   -0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.0986    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -0.6258    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2664   -0.0270   -0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    1.6779    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.2753    0.4194 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
  9  4  1  0
 17 11  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
M  CHG  2  25   1  27  -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  -8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      12.003  -5.390   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0      13.337  -6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O-1
HETATM   19  N   UNK     0      -1.334  -3.850   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   26 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   27 Cl   UNK     0      -4.001  -5.390   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    4   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   21                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0255647
HETATM    1  O1  UNL     1       0.480  -1.614   0.310  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.666  -1.883  -0.905  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.464  -2.313  -1.720  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.750  -2.391  -1.024  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.308  -3.591  -0.631  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.496  -3.706   0.016  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.209  -2.568   0.312  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.704  -1.340  -0.055  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.472  -1.259  -0.723  1.00  0.00           C  
HETATM   10  N1  UNL     1      -1.969   0.006  -1.091  1.00  0.00           N  
HETATM   11  C9  UNL     1      -2.645   1.225  -0.834  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.534   1.759  -1.739  1.00  0.00           C  
HETATM   13 CL1  UNL     1      -3.829   0.906  -3.240  1.00  0.00          CL  
HETATM   14  C11 UNL     1      -4.211   2.946  -1.516  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.980   3.624  -0.327  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.089   3.107   0.601  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.430   1.912   0.338  1.00  0.00           C  
HETATM   18 CL2  UNL     1      -1.309   1.255   1.497  1.00  0.00          CL  
HETATM   19  O2  UNL     1       1.930  -1.752  -1.391  1.00  0.00           O  
HETATM   20  C15 UNL     1       3.074  -1.362  -0.736  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.074  -0.005  -0.114  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.448   0.162   0.534  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.623   1.482   1.210  1.00  0.00           C  
HETATM   24  O3  UNL     1       5.927   1.497   1.758  1.00  0.00           O  
HETATM   25  N2  UNL     1       6.403   2.588   2.453  1.00  0.00           N1+
HETATM   26  O4  UNL     1       7.381   2.533   3.206  1.00  0.00           O  
HETATM   27  O5  UNL     1       5.757   3.777   2.295  1.00  0.00           O1-
HETATM   28  H1  UNL     1      -0.195  -3.299  -2.210  1.00  0.00           H  
HETATM   29  H2  UNL     1      -0.595  -1.628  -2.598  1.00  0.00           H  
HETATM   30  H3  UNL     1      -1.755  -4.486  -0.859  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.856  -4.711   0.287  1.00  0.00           H  
HETATM   32  H5  UNL     1      -5.154  -2.674   0.828  1.00  0.00           H  
HETATM   33  H6  UNL     1      -4.276  -0.451   0.184  1.00  0.00           H  
HETATM   34  H7  UNL     1      -1.052   0.065  -1.577  1.00  0.00           H  
HETATM   35  H8  UNL     1      -4.909   3.355  -2.239  1.00  0.00           H  
HETATM   36  H9  UNL     1      -4.491   4.559  -0.113  1.00  0.00           H  
HETATM   37  H10 UNL     1      -2.888   3.623   1.549  1.00  0.00           H  
HETATM   38  H11 UNL     1       3.296  -2.103   0.068  1.00  0.00           H  
HETATM   39  H12 UNL     1       3.939  -1.416  -1.430  1.00  0.00           H  
HETATM   40  H13 UNL     1       2.984   0.769  -0.881  1.00  0.00           H  
HETATM   41  H14 UNL     1       2.329   0.099   0.698  1.00  0.00           H  
HETATM   42  H15 UNL     1       4.482  -0.626   1.342  1.00  0.00           H  
HETATM   43  H16 UNL     1       5.266  -0.027  -0.162  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.895   1.678   2.002  1.00  0.00           H  
HETATM   45  H18 UNL     1       4.618   2.275   0.419  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   28   29
CONECT    4    5    5    9
CONECT    5    6   30
CONECT    6    7    7   31
CONECT    7    8   32
CONECT    8    9    9   33
CONECT    9   10
CONECT   10   11   34
CONECT   11   12   12   17
CONECT   12   13   14
CONECT   14   15   15   35
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18
CONECT   19   20
CONECT   20   21   38   39
CONECT   21   22   40   41
CONECT   22   23   42   43
CONECT   23   24   44   45
CONECT   24   25
CONECT   25   26   26   27
END

HMDB0255647
     RDKit          3D
Nitrofenac
 45 46  0  0  0  0  0  0  0  0999 V2000
    0.4800   -1.6143    0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -1.8827   -0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4644   -2.3134   -1.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7497   -2.3912   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3076   -3.5906   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4961   -3.7063    0.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2092   -2.5676    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039   -1.3401   -0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4715   -1.2585   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9692    0.0063   -1.0905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6450    1.2250   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5342    1.7585   -1.7389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8292    0.9061   -3.2399 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113    2.9459   -1.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9798    3.6240   -0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0890    3.1074    0.6013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303    1.9123    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3092    1.2554    1.4967 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -1.7525   -1.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739   -1.3618   -0.7361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739   -0.0047   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4476    0.1619    0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    1.4816    1.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9271    1.4970    1.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4031    2.5882    2.4534 N   0  0  0  0  0  4  0  0  0  0  0  0
    7.3812    2.5325    3.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7568    3.7768    2.2946 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1947   -3.2986   -2.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -1.6277   -2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -4.4859   -0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8564   -4.7108    0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1545   -2.6736    0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -0.4506    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    0.0652   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9089    3.3548   -2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4911    4.5593   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883    3.6229    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2962   -2.1026    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394   -1.4160   -1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    0.7691   -0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.0986    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4818   -0.6258    1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2664   -0.0270   -0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    1.6779    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.2753    0.4194 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
  9  4  1  0
 17 11  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 23 45  1  0
M  CHG  2  25   1  27  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-((2,6-Dichlorophenyl) amino)benzeneacetate-4-hydroxybutylnitric ester	HMDB

Chemical Formula

C₁₈H₁₈Cl₂N₂O₅

Average Molecular Weight

413.25

Monoisotopic Molecular Weight

412.0592771

IUPAC Name

4-(nitrooxy)butyl 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate

Traditional Name

4-(nitrooxy)butyl {2-[(2,6-dichlorophenyl)amino]phenyl}acetate

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)OCCCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl

InChI Identifier

InChI=1S/C18H18Cl2N2O5/c19-14-7-5-8-15(20)18(14)21-16-9-2-1-6-13(16)12-17(23)26-10-3-4-11-27-22(24)25/h1-2,5-9,21H,3-4,10-12H2

InChI Key

CQVHWLHWUZRTQC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

Aniline or substituted anilines
1,3-dichlorobenzene
Aryl halide
Aryl chloride
Alkyl nitrate
Organic nitrate
Organic nitro compound
Organic nitric acid or derivatives
Carboxylic acid ester
Amino acid or derivatives
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Amine
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	5.23	ALOGPS
logP	4.99	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	16.4	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	90.7 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	101.72 m³·mol⁻¹	ChemAxon
Polarizability	40.19 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]+	181.185	30932474
DeepCCS	[M-H]-	178.827	30932474
DeepCCS	[M-2H]-	212.52	30932474
DeepCCS	[M+Na]+	187.747	30932474
AllCCS	[M+H]+	186.3	32859911
AllCCS	[M+H-H2O]+	183.9	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.0	32859911
AllCCS	[M-H]-	187.1	32859911
AllCCS	[M+Na-2H]-	186.9	32859911
AllCCS	[M+HCOO]-	186.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nitrofenac	[O-][N+](=O)OCCCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	4679.5	Standard polar	33892256
Nitrofenac	[O-][N+](=O)OCCCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	3031.3	Standard non polar	33892256
Nitrofenac	[O-][N+](=O)OCCCCOC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	3042.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nitrofenac,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1CC(=O)OCCCCO[N+](=O)[O-])C1=C(Cl)C=CC=C1Cl	3019.2	Semi standard non polar	33892256
Nitrofenac,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1CC(=O)OCCCCO[N+](=O)[O-])C1=C(Cl)C=CC=C1Cl	2891.9	Standard non polar	33892256
Nitrofenac,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1CC(=O)OCCCCO[N+](=O)[O-])C1=C(Cl)C=CC=C1Cl	4044.8	Standard polar	33892256
Nitrofenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1CC(=O)OCCCCO[N+](=O)[O-])C1=C(Cl)C=CC=C1Cl	3207.2	Semi standard non polar	33892256
Nitrofenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1CC(=O)OCCCCO[N+](=O)[O-])C1=C(Cl)C=CC=C1Cl	3092.9	Standard non polar	33892256
Nitrofenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1CC(=O)OCCCCO[N+](=O)[O-])C1=C(Cl)C=CC=C1Cl	4050.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrofenac GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1190000000-cb1db757a2ae386cfbed	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitrofenac 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

117353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132976

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 Nitrofenac (HMDB0255647)

MOL for HMDB0255647 (Nitrofenac)

3D MOL for HMDB0255647 (Nitrofenac)

3D SDF for HMDB0255647 (Nitrofenac)

3D-SDF for HMDB0255647 (Nitrofenac)

PDB for HMDB0255647 (Nitrofenac)

3D PDB for HMDB0255647 (Nitrofenac)

SMILES for HMDB0255647 (Nitrofenac)

INCHI for HMDB0255647 (Nitrofenac)

Structure for HMDB0255647 (Nitrofenac)

3D Structure for HMDB0255647 (Nitrofenac)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra