Np mrd loader

Showing NP-Card for p-Hydroxyphenylacetic acid (NP0000436)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-10 18:04:08 UTC
NP-MRD IDNP0000436
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Hydroxyphenylacetic acid
DescriptionP-hydroxyphenylacetic acid, also known as 4-Hydroxybenzeneacetate or Parahydroxy phenylacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that a unsubstituted at the 2-position. P-hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic. P-hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate. P-hydroxyphenylacetic acid can be found throughout numerous foods such as Olives, Cocoa beans, Oats, and Mushrooms. P-hydroxyphenylacetic acid can be found throughout all human tissues; and in all biofluids. Within a cell, P-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000436 (p-Hydroxyphenylacetic acid)


  Mrv1652303182019222D          

 11 11  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002   -1.3275    0.0000 O   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
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000436 (p-Hydroxyphenylacetic acid)

HMDB0000020
     RDKit          3D
p-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.4487    0.0429    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225    0.1968    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628   -0.4203   -0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.0739   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2892    0.4737   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248   -0.0988   -1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4754   -0.6740   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -0.7166   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100   -1.3120    0.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903   -0.1298    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.4544    1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.0323   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451    2.0547    0.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0052    1.2732   -1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -0.0591   -2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -1.1181   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -0.7342   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885   -0.1594    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0791    0.8850    1.9925 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  2  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0000436 (p-Hydroxyphenylacetic acid)


  Mrv1652303182019222D          

 11 11  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2002   -1.3275    0.0000 O   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
  6  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000436

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)

> <INCHI_KEY>
XQXPVVBIMDBYFF-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.826780263933244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.3074287836666667

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.508099347910598

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9984367127077793

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9585563884254755

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
39.3465

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000436 (p-Hydroxyphenylacetic acid)

HMDB0000020
     RDKit          3D
p-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.4487    0.0429    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225    0.1968    0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6628   -0.4203   -0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.0739   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2892    0.4737   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248   -0.0988   -1.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4754   -0.6740   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2431   -0.7166   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5100   -1.3120    0.0105 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6903   -0.1298    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.4544    1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.0323   -0.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451    2.0547    0.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0052    1.2732   -1.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3777   -0.0591   -2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826   -1.1181   -2.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3170   -0.7342   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885   -0.1594    2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0791    0.8850    1.9925 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  2  0
 11  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0000436 (p-Hydroxyphenylacetic acid)

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.042  -3.248   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.960  -0.168   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.374  -2.478   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7   11   10                                                  
CONECT    9    4                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
Download

3D PDB for NP0000436 (p-Hydroxyphenylacetic acid)

COMPND    HMDB0000020
HETATM    1  O1  UNL     1      -2.449   0.043   1.827  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.623   0.197   0.593  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.663  -0.420  -0.072  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.646   1.074  -0.094  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.289   0.474  -0.078  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.225  -0.099  -1.228  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.475  -0.674  -1.158  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.243  -0.717  -0.017  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.510  -1.312   0.010  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.690  -0.130   1.120  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.439   0.454   1.073  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.453  -1.032  -0.883  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.645   2.055   0.394  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.005   1.273  -1.139  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.378  -0.059  -2.125  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.883  -1.118  -2.050  1.00  0.00           H  
HETATM   17  H6  UNL     1       4.317  -0.734  -0.197  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.289  -0.159   2.032  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.079   0.885   1.993  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6    6   11
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   10
CONECT    9   17
CONECT   10   11   11   18
CONECT   11   19
END
Download

SMILES for NP0000436 (p-Hydroxyphenylacetic acid)

OC(=O)CC1=CC=C(O)C=C1
Download

INCHI for NP0000436 (p-Hydroxyphenylacetic acid)

InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
Download
View in JSmol
Synonyms
ValueSource
(p-Hydroxyphenyl)acetic acidChEBI
4-CarboxymethylphenolChEBI
4-Hydroxybenzeneacetic acidChEBI
4-HydroxyphenylacetateChEBI
4-Hydroxyphenylacetic acidKegg
(p-Hydroxyphenyl)acetateGenerator
4-HydroxybenzeneacetateGenerator
p-HydroxyphenylacetateGenerator
(4-Hydroxy-phenyl)-acetateHMDB
(4-Hydroxy-phenyl)-acetic acidHMDB
(4-Hydroxy-phenyl)-essigsaeureHMDB
(4-Hydroxyphenyl)acetateHMDB
(4-Hydroxyphenyl)acetic acidHMDB
(p-Hydroxyphenyl)-acetateHMDB
(p-Hydroxyphenyl)-acetic acidHMDB
4-Hydroxy-benzeneacetateHMDB
4-Hydroxy-benzeneacetic acidHMDB
4-Hydroxyphenyl-acetic acidHMDB
Parahydroxy phenylacetateHMDB
Parahydroxy phenylacetic acidHMDB
ParahydroxyphenylacetateHMDB
Para-hydroxyphenylacetic acidHMDB
4'-Hydroxyphenylacetic acidHMDB
2-(4-Hydroxyphenyl)acetic acidHMDB
p-Hydroxyphenylacetic acidChEBI
4-Hydroxyphenylethanoic acid
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name2-(4-hydroxyphenyl)acetic acid
Traditional Name4-hydroxyphenylacetic acid
CAS Registry Number156-38-7
SMILES
OC(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyXQXPVVBIMDBYFF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-10View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-01View Spectrum
Species
Species of Origin
Species NameSourceReference
Althaea cannabinaLOTUS Database
Althaea officinalisLOTUS Database
Arbutus unedoLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Cichorium intybusLOTUS Database
Citrus limoniaKNApSAcK Database
Drypetes gossweileriLOTUS Database
Epichloe typhinaLOTUS Database
Ficaria vernaLOTUS Database
Forsythia suspensaLOTUS Database
Forsythia viridissimaLOTUS Database
Grosmannia crassivaginataLOTUS Database
Homo sapiensLOTUS Database
Isatis tinctoriaLOTUS Database
Lupinus angustifoliusLOTUS Database
Melilotus officinalisKNApSAcK Database
Moringa oleiferaLOTUS Database
Oenothera biennisLOTUS Database
Olea europaeaLOTUS Database
Ophiocordyceps sinensisLOTUS Database
Pelargonium reniformeKNApSAcK Database
Penicillium chrysogenumLOTUS Database
Penicillium herqueiLOTUS Database
Penicillium javanicumLOTUS Database
Pinus pinasterLOTUS Database
Pteroxygonum giraldiiLOTUS Database
Sargentodoxa cuneataLOTUS Database
Secamone afzeliiLOTUS Database
Senecio scandensKNApSAcK Database
Taraxacum formosanumLOTUS Database
Thanatephorus cucumerisLOTUS Database
Tragopogon pratensisLOTUS Database
Undaria pinnatifidaLOTUS Database
Vaccinium macrocarponLOTUS Database
Vitis viniferaLOTUS Database
Zea maysLOTUS Database
Zyzzya fuliginosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling Point346.63 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility60.7 mg/mLNot Available
LogP0.75Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility7.12 g/LALOGPS
logP0.93ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000020
DrugBank IDNot Available
Phenol Explorer Compound ID573
FoodDB IDFDB010534
KNApSAcK IDC00050490
Chemspider ID124
KEGG Compound IDC00642
BioCyc ID4-HYDROXYPHENYLACETATE
BiGG ID35599
Wikipedia Link4-hydroxyphenylacetic_acid
METLIN ID130
PubChem Compound127
PDB IDNot Available
ChEBI ID18101
Good Scents IDrw1203851
References
General References
  1. Hirota S, Takahama U, Ly TN, Yamauchi R: Quercetin-dependent inhibition of nitration induced by peroxidase/H2O2/nitrite systems in human saliva and characterization of an oxidation product of quercetin formed during the inhibition. J Agric Food Chem. 2005 May 4;53(9):3265-72. [PubMed:15853358 ]
  2. 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 ]
  3. Kobayashi K, Koide Y, Shohmori T: Determination of p-hydroxyphenylacetic acid in cerebrospinal fluid by high-performance liquid chromatography with electrochemical detection. Clin Chim Acta. 1982 Aug 4;123(1-2):161-8. [PubMed:7116636 ]
  4. Tyce GM, Stockard J, Sharpless NS, Muenter MD: Excretion of amines and their metabolites by two patients in hepatic coma treated with L-dopa. Clin Pharmacol Ther. 1983 Sep;34(3):390-8. [PubMed:6883916 ]
  5. Young SN, Davis BA, Gauthier S: Precursors and metabolites of phenylethylamine, m and p-tyramine and tryptamine in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1982 Jul;45(7):633-9. [PubMed:6181210 ]
  6. Muskiet FA, Groen A: Urinary excretion of conjugated homovanillic acid, 3,4-dihydroxyphenylacetic acid, p-hydroxyphenylacetic acid, and vanillic acid by persons on their usual diet and patients with neuroblastoma. Clin Chem. 1979 Jul;25(7):1281-4. [PubMed:455649 ]
  7. 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 ]
  8. Takahama U, Hirota S, Nishioka T, Oniki T: Human salivary peroxidase-catalyzed oxidation of nitrite and nitration of salivary components 4-hydroxyphenylacetic acid and proteins. Arch Oral Biol. 2003 Oct;48(10):679-90. [PubMed:12971945 ]
  9. Quijano C, Hernandez-Saavedra D, Castro L, McCord JM, Freeman BA, Radi R: Reaction of peroxynitrite with Mn-superoxide dismutase. Role of the metal center in decomposition kinetics and nitration. J Biol Chem. 2001 Apr 13;276(15):11631-8. Epub 2001 Jan 4. [PubMed:11152462 ]
  10. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
  11. Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72. [PubMed:15721987 ]
  12. Shen YP, Liao YL, Lu Q, He X, Yan ZB, Liu JZ: ATP and NADPH engineering of Escherichia coli to improve the production of 4-hydroxyphenylacetic acid using CRISPRi. Biotechnol Biofuels. 2021 Apr 20;14(1):100. doi: 10.1186/s13068-021-01954-6. [PubMed:33879249 ]