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Showing metabocard for 4-hydroxy-3-nitrophenylacetate (HMDB0062403)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-21 06:14:48 UTC
Update Date2023-02-21 17:30:52 UTC
HMDB IDHMDB0062403
Secondary Accession Numbers
  • HMDB62403
Metabolite Identification
Common Name4-hydroxy-3-nitrophenylacetate
Description4-hydroxy-3-nitrophenylacetate, also known as 3-nitro-4-hydroxyphenylacetic acid, is slightly soluble (in water). It is a mildly acidic compound. This metabolite is a member of the class of compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. Free nitrotyrosine undergoes metabolism to form 3-nitro-4-hydroxyphenylacetic acid (NHPA) which is excreted in the urine (Wikipedia). However, it is not known whether NHPA is derived exclusively from metabolism of nitrotyrosine, or whether it can be formed by nitration of circulating para -hydroxyphenylacetic acid (PHPA), a metabolite of tyrosine (PMID: 12797864 ). Since the plasma concentration of PHPA is markedly higher than free nitrotyrosine (approx. 400-fold), the nitration of high-circulating endogenous PHPA to form NHPA becomes very significant and accounts for the majority of NHPA excreted in urine (PMID: 12797864 ).
Structure
Data?1677000652
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)


  Mrv1652305171803112D          

 14 14  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  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
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 10  5  1  0  0  0  0
 14  8  1  0  0  0  0
M  CHG  2  11   1  12  -1
M  END
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3D MOL for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

HMDB0062403
     RDKit          3D
4-hydroxy-3-nitrophenylacetate
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.3470    0.0351    1.5483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436   -0.3603    0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1700   -0.7449    0.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -0.4037   -0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6213    0.0574   -0.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2556    1.3759   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    1.8070   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    0.8949    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    1.2758    0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -0.4410    0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614   -1.3587    0.5303 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.5774   -0.9644    1.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6699   -2.6847    0.1085 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.3487   -0.8411   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4768   -1.6985    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -1.4533   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040    0.2357   -1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    2.0925   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012    2.8503   -0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340    2.2123    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0877   -1.8863    0.0004 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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14  5  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 14 21  1  0
M  CHG  2  11   1  13  -1
M  END
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3D SDF for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)


  Mrv1652305171803112D          

 14 14  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  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
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 10  5  1  0  0  0  0
 14  8  1  0  0  0  0
M  CHG  2  11   1  12  -1
M  END
> <DATABASE_ID>
HMDB0062403

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO5/c10-7-2-1-5(4-8(11)12)3-6(7)9(13)14/h1-3,10H,4H2,(H,11,12)

> <INCHI_KEY>
QBHBHOSRLDPIHG-UHFFFAOYSA-N

> <FORMULA>
C8H7NO5

> <MOLECULAR_WEIGHT>
197.1449

> <EXACT_MASS>
197.032422339

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.100612415475975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxy-3-nitrophenyl)acetic acid

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.2474129729999999

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.602306026638564

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0188807984153976

> <JCHEM_PKA_STRONGEST_BASIC>
-6.879134626471463

> <JCHEM_POLAR_SURFACE_AREA>
100.67

> <JCHEM_REFRACTIVITY>
45.667

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-hydroxy-3-nitrophenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

HMDB0062403
     RDKit          3D
4-hydroxy-3-nitrophenylacetate
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.3470    0.0351    1.5483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8436   -0.3603    0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1700   -0.7449    0.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096   -0.4037   -0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6213    0.0574   -0.4855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2556    1.3759   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    1.8070   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9862    0.8949    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    1.2758    0.2525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545   -0.4410    0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614   -1.3587    0.5303 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.5774   -0.9644    1.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6699   -2.6847    0.1085 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.3487   -0.8411   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4768   -1.6985    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -1.4533   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040    0.2357   -1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    2.0925   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012    2.8503   -0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340    2.2123    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0877   -1.8863    0.0004 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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  2  0
 14  5  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  6 18  1  0
  7 19  1  0
  9 20  1  0
 14 21  1  0
M  CHG  2  11   1  13  -1
M  END
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PDB for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+1
HETATM   12  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

COMPND    HMDB0062403
HETATM    1  O1  UNL     1      -2.347   0.035   1.548  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.844  -0.360   0.470  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.170  -0.745   0.458  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.010  -0.404  -0.741  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.621   0.057  -0.486  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.256   1.376  -0.613  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.029   1.807  -0.376  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.986   0.895   0.001  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.295   1.276   0.253  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.655  -0.441   0.140  1.00  0.00           C  
HETATM   11  N1  UNL     1       2.661  -1.359   0.530  1.00  0.00           N1+
HETATM   12  O4  UNL     1       3.577  -0.964   1.282  1.00  0.00           O  
HETATM   13  O5  UNL     1       2.670  -2.685   0.108  1.00  0.00           O1-
HETATM   14  C8  UNL     1       0.349  -0.841  -0.107  1.00  0.00           C  
HETATM   15  H1  UNL     1      -4.477  -1.699   0.386  1.00  0.00           H  
HETATM   16  H2  UNL     1      -1.994  -1.453  -1.158  1.00  0.00           H  
HETATM   17  H3  UNL     1      -2.504   0.236  -1.527  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.023   2.093  -0.914  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.301   2.850  -0.481  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.634   2.212   0.181  1.00  0.00           H  
HETATM   21  H7  UNL     1       0.088  -1.886   0.000  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5   16   17
CONECT    5    6    6   14
CONECT    6    7   18
CONECT    7    8    8   19
CONECT    8    9   10
CONECT    9   20
CONECT   10   11   14   14
CONECT   11   12   12   13
CONECT   14   21
END
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SMILES for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O
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INCHI for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

InChI=1S/C8H7NO5/c10-7-2-1-5(4-8(11)12)3-6(7)9(13)14/h1-3,10H,4H2,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-(4-HYDROXY-3-nitrophenyl)acetIC ACIDChEBI
4-Hydroxy-3-nitrophenylacetic acidChEBI
NO2hpaChEBI
2-(4-HYDROXY-3-nitrophenyl)acetateGenerator
NP-HaptenHMDB
Hapten NPHMDB
(4-Hydroxy-3-nitrophenyl)acetylHMDB
4-Hydroxy-3-nitrophenylacetylHMDB
3-Nitro-4-hydroxyphenylacetic acidHMDB
4-OHNOPHAXHMDB
4-Hydroxy-3-nitrophenyl acetylHMDB
4-Hydroxy-5-nitrophenyl acetic acidHMDB
4-Hydroxy-3-nitrophenylacetateGenerator
Chemical FormulaC8H7NO5
Average Molecular Weight197.1449
Monoisotopic Molecular Weight197.032422339
IUPAC Name2-(4-hydroxy-3-nitrophenyl)acetic acid
Traditional Name(4-hydroxy-3-nitrophenyl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C8H7NO5/c10-7-2-1-5(4-8(11)12)3-6(7)9(13)14/h1-3,10H,4H2,(H,11,12)
InChI KeyQBHBHOSRLDPIHG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassNitrophenols
Direct ParentNitrophenols
Alternative Parents
Substituents
  • Nitrophenol
  • Nitrobenzene
  • Nitroaromatic compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • C-nitro compound
  • Organic nitro compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • 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 Solubility2.74 g/lALOGPS
LogP1.14ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.01ALOGPS
logP1.25ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.02ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.67 m³·mol⁻¹ChemAxon
Polarizability17.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.15431661259
DarkChem[M-H]-141.39131661259
DeepCCS[M+H]+134.63130932474
DeepCCS[M-H]-131.37130932474
DeepCCS[M-2H]-167.25130932474
DeepCCS[M+Na]+142.9630932474
AllCCS[M+H]+140.832859911
AllCCS[M+H-H2O]+136.732859911
AllCCS[M+NH4]+144.732859911
AllCCS[M+Na]+145.832859911
AllCCS[M-H]-136.132859911
AllCCS[M+Na-2H]-136.532859911
AllCCS[M+HCOO]-137.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.02 minutes32390414
Predicted by Siyang on May 30, 202211.4784 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.34 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1454.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid360.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid121.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid210.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid97.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid428.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid387.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)253.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid891.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid378.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1155.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid288.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid355.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate532.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA299.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water256.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-hydroxy-3-nitrophenylacetateOC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O2870.8Standard polar33892256
4-hydroxy-3-nitrophenylacetateOC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O1558.1Standard non polar33892256
4-hydroxy-3-nitrophenylacetateOC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O1762.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-hydroxy-3-nitrophenylacetate,1TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=C(O)C([N+](=O)[O-])=C11857.8Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1[N+](=O)[O-]1892.3Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,2TMS,isomer #1C[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C11968.3Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O)C([N+](=O)[O-])=C12108.8Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1[N+](=O)[O-]2194.1Semi standard non polar33892256
4-hydroxy-3-nitrophenylacetate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C12455.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxy-3-nitrophenylacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-6900000000-e5a377fa30be1cf9599c2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-hydroxy-3-nitrophenylacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Positive-QTOFsplash10-0002-0900000000-79a4c32d8d4140950f152017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Positive-QTOFsplash10-006x-0900000000-f46310eb481a53ce8a732017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Positive-QTOFsplash10-006y-2900000000-1198cd045e8ca04126ed2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Negative-QTOFsplash10-0002-0900000000-edf1df88d14334cd76092017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Negative-QTOFsplash10-0002-1900000000-de624db331c7d7c2ad292017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Negative-QTOFsplash10-0a4i-9400000000-fd42775792f6028d92ba2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Negative-QTOFsplash10-001i-0900000000-4322905b69ee20c9fe7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Negative-QTOFsplash10-0zgi-0900000000-32060e9dd1d20b4cbfba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Negative-QTOFsplash10-0002-9600000000-ddfb1263633ffe02e6082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Positive-QTOFsplash10-0002-0900000000-cd198104c5c4f1e9625d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Positive-QTOFsplash10-0udj-0900000000-740cc01eff010d7e68262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Positive-QTOFsplash10-0a4i-8900000000-e126a2d3aff76df1c47b2021-09-23Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08294
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound447364
PDB IDNPA
ChEBI ID546274
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. Takahama U, Oniki T, Murata H: The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002 May 8;518(1-3):116-8. [PubMed:11997029 ]
  2. Mani AR, Pannala AS, Orie NN, Ollosson R, Harry D, Rice-Evans CA, Moore KP: Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine. Biochem J. 2003 Sep 1;374(Pt 2):521-7. [PubMed:12797864 ]