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Showing metabocard for 4-Nitrophenylacetic acid (HMDB0246546)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:33:45 UTC
Update Date2021-09-26 22:55:42 UTC
HMDB IDHMDB0246546
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Nitrophenylacetic acid
Description(4-nitrophenyl)acetic acid, also known as 4-nitrobenzeneacetate or p-nitrophenylacetate, belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. Based on a literature review very few articles have been published on (4-nitrophenyl)acetic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-nitrophenylacetic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Nitrophenylacetic acid 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0246546 (4-Nitrophenylacetic acid)

AAN
  Mrv0541 02241213212D          

 13 13  0  0  0  0            999 V2000
    1.7401    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0256    0.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033   -0.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1178   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.9745    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.5467   -0.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -1.7995    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.1178    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    0.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546    0.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401   -0.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  2  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  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
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10 11  2  0  0  0  0
M  CHG  2   7   1   9  -1
M  END
Download

3D MOL for HMDB0246546 (4-Nitrophenylacetic acid)

HMDB0246546
     RDKit          3D
4-Nitrophenylacetic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.1222   -1.6300   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694   -0.6340   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484   -0.6033   -0.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0338    0.5445    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674    0.3238    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1765    0.6644   -0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    0.4719   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -0.0824    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6262   -0.2693   -0.0444 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.2826    0.0400   -1.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2805   -0.8121    1.0257 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.4836   -0.4233    1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.2217    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7161   -0.0139    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4114    0.7251    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    1.4230   -0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    1.1046   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    0.7372   -1.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0095   -0.8553    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795   -0.4893    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13  5  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
 12 19  1  0
 13 20  1  0
M  CHG  2   9   1  11  -1
M  END
Download

3D SDF for HMDB0246546 (4-Nitrophenylacetic acid)

AAN
  Mrv0541 02241213212D          

 13 13  0  0  0  0            999 V2000
    1.7401    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0256    0.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033   -0.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1178   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -0.9745    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.5467   -0.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8323   -1.7995    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.1178    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    0.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546    0.6755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7401   -0.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  2  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  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
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10 11  2  0  0  0  0
M  CHG  2   7   1   9  -1
M  END
> <DATABASE_ID>
HMDB0246546

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO4/c10-8(11)5-6-1-3-7(4-2-6)9(12)13/h1-4H,5H2,(H,10,11)

> <INCHI_KEY>
YBADLXQNJCMBKR-UHFFFAOYSA-N

> <FORMULA>
C8H7NO4

> <MOLECULAR_WEIGHT>
181.1455

> <EXACT_MASS>
181.037507717

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.26938775574761

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-nitrophenyl)acetic acid

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.5509782946666664

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0675888589048617

> <JCHEM_PKA_STRONGEST_BASIC>
-9.695921006974134

> <JCHEM_POLAR_SURFACE_AREA>
83.12

> <JCHEM_REFRACTIVITY>
44.6903

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-nitrophenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0246546 (4-Nitrophenylacetic acid)

HMDB0246546
     RDKit          3D
4-Nitrophenylacetic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.1222   -1.6300   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7694   -0.6340   -0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484   -0.6033   -0.4281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0338    0.5445    0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674    0.3238    0.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1765    0.6644   -0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    0.4719   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -0.0824    0.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6262   -0.2693   -0.0444 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.2826    0.0400   -1.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2805   -0.8121    1.0257 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.4836   -0.4233    1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137   -0.2217    1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7161   -0.0139    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4114    0.7251    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    1.4230   -0.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    1.1046   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    0.7372   -1.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0095   -0.8553    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4795   -0.4893    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13  5  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
 12 19  1  0
 13 20  1  0
M  CHG  2   9   1  11  -1
M  END
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PDB for HMDB0246546 (4-Nitrophenylacetic acid)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: AAN                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.248   0.491   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.914   1.261   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.581   0.491   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.581  -1.049   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.753  -1.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.087  -1.049   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.420  -1.819   0.000  0.00  0.00           N+1
HETATM    8  O   UNK     0      -4.754  -1.049   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.420  -3.359   0.000  0.00  0.00           O-1
HETATM   10  C   UNK     0      -2.087   0.491   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.753   1.261   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.582   1.261   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.248  -1.049   0.000  0.00  0.00           O+0
CONECT    1    2   12   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11    3   10                                                       
CONECT   12    1                                                            
CONECT   13    1                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0246546 (4-Nitrophenylacetic acid)

COMPND    HMDB0246546
HETATM    1  O1  UNL     1      -2.122  -1.630  -0.751  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.769  -0.634  -0.377  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.148  -0.603  -0.428  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.034   0.544   0.133  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.567   0.324   0.111  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.176   0.664  -1.000  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.536   0.472  -1.050  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.225  -0.082   0.035  1.00  0.00           C  
HETATM    9  N1  UNL     1       3.626  -0.269  -0.044  1.00  0.00           N1+
HETATM   10  O3  UNL     1       4.283   0.040  -1.046  1.00  0.00           O  
HETATM   11  O4  UNL     1       4.281  -0.812   1.026  1.00  0.00           O1-
HETATM   12  C7  UNL     1       1.484  -0.423   1.145  1.00  0.00           C  
HETATM   13  C8  UNL     1       0.114  -0.222   1.177  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.716  -0.014   0.154  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.411   0.725   1.175  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.321   1.423  -0.497  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.307   1.105  -1.886  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.143   0.737  -1.926  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.010  -0.855   1.995  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.479  -0.489   2.053  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6    6   13
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9   12
CONECT    9   10   10   11
CONECT   12   13   13   19
CONECT   13   20
END
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SMILES for HMDB0246546 (4-Nitrophenylacetic acid)

OC(=O)CC1=CC=C(C=C1)[N+]([O-])=O
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INCHI for HMDB0246546 (4-Nitrophenylacetic acid)

InChI=1S/C8H7NO4/c10-8(11)5-6-1-3-7(4-2-6)9(12)13/h1-4H,5H2,(H,10,11)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-(p-Nitrophenyl)acetic acidChEBI
4-Nitrobenzeneacetic acidChEBI
4-Nitrophenylacetic acidChEBI
p-Nitrophenylacetic acidChEBI
2-(p-Nitrophenyl)acetateGenerator
4-NitrobenzeneacetateGenerator
4-NitrophenylacetateGenerator
p-NitrophenylacetateGenerator
(4-Nitrophenyl)acetateGenerator
2-(4-Nitrophenyl)acetateGenerator
2-(4-Nitrophenoxy)acetic acidMeSH
Chemical FormulaC8H7NO4
Average Molecular Weight181.1455
Monoisotopic Molecular Weight181.037507717
IUPAC Name2-(4-nitrophenyl)acetic acid
Traditional Name2-(4-nitrophenyl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C8H7NO4/c10-8(11)5-6-1-3-7(4-2-6)9(12)13/h1-4H,5H2,(H,10,11)
InChI KeyYBADLXQNJCMBKR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • C-nitro compound
  • Organic nitro compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4500
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID40443
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]