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Showing NP-Card for p-hydroxy phenylacetic acid (NP0332544)

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Record Information
Version1.0
Created at2024-02-22 12:00:52 UTC
Updated at2024-04-19 10:10:58 UTC
NP-MRD IDNP0332544
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-hydroxy phenylacetic acid
DescriptionP-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate or 4-carboxymethylphenol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. P-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to plants to humans. In humans, p-hydroxyphenylacetic acid is involved in the metabolic disorder called tyrosinemia type I. P-Hydroxyphenylacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. P-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer, spina bifida, perillyl alcohol administration for cancer treatment, and schizophrenia; p-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria. It was first documented in 2017 (PMID: 29096095). Based on a literature review a significant number of articles have been published on p-Hydroxyphenylacetic acid (PMID: 34475403) (PMID: 34251171) (PMID: 33903806) (PMID: 33086681) (PMID: 32889133) (PMID: 32844861).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0332544 (p-hydroxy phenylacetic 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 NP0332544 (p-hydroxy phenylacetic 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 NP0332544 (p-hydroxy phenylacetic 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>
NP0332544

> <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 NP0332544 (p-hydroxy phenylacetic 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 NP0332544 (p-hydroxy phenylacetic 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
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3D PDB for NP0332544 (p-hydroxy phenylacetic 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
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SMILES for NP0332544 (p-hydroxy phenylacetic acid)

OC(=O)CC1=CC=C(O)C=C1
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INCHI for NP0332544 (p-hydroxy phenylacetic acid)

InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
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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 NumberNot Available
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 NMR[13C, ] NMR Spectrum (2D, 151 MHz, C2D6OS, experimental)yijing0212@163.com南方医科大学Jing Yi2024-02-22View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)yijing0212@163.com南方医科大学Jing Yi2024-02-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, C2D6OS, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150.918653341 MHz, C2D6OS, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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. Yan Y, Ren S, Duan Y, Lu C, Niu Y, Wang Z, Inglis B, Ji W, Zheng Y, Si W: Gut microbiota and metabolites of alpha-synuclein transgenic monkey models with early stage of Parkinson's disease. NPJ Biofilms Microbiomes. 2021 Sep 2;7(1):69. doi: 10.1038/s41522-021-00242-3. [PubMed:34475403 ]
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