Np mrd loader

Showing NP-Card for 3-Hydroxyphenylacetic acid (NP0000982)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:19:13 UTC
NP-MRD IDNP0000982
Natural Product DOIhttps://doi.org/10.57994/1676
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Hydroxyphenylacetic acid
Description3-Hydroxyphenylacetic acid is a rutin metabolite and an antioxidant. It has a protective biological activity in human. It is a substrate of enzyme 4-hydroxyphenylacetate 3-monooxygenase [EC 1.14.13.3] In the pathway tyrosine metabolism (KEGG, PMID 155437 ). 3-Hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000982 (3-Hydroxyphenylacetic acid)


  Mrv1652305261923572D          

 11 11  0  0  0  0            999 V2000
    1.6500   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0000982 (3-Hydroxyphenylacetic acid)

HMDB0000440
     RDKit          3D
3-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8465    1.6047    1.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    0.6502    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    0.5211    0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -0.3217   -0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -0.1082   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    0.6857   -1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380    0.8583   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.2457   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -0.5478    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.1529    1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.7281    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3452    0.0522    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687   -1.3372    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329   -0.3411   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.1765   -1.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    1.4756   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372    0.3712   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -1.7365    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1915   -1.3677    1.4824 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  1  0
  9 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
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0000982 (3-Hydroxyphenylacetic acid)


  Mrv1652305261923572D          

 11 11  0  0  0  0            999 V2000
    1.6500   -1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000982

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
FVMDYYGIDFPZAX-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.777919898848198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.3074287836666667

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.470982050154852

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9988857987295043

> <JCHEM_PKA_STRONGEST_BASIC>
-5.965684195856604

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
39.346500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000982 (3-Hydroxyphenylacetic acid)

HMDB0000440
     RDKit          3D
3-Hydroxyphenylacetic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.8465    1.6047    1.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824    0.6502    0.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    0.5211    0.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -0.3217   -0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244   -0.1082   -0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3900    0.6857   -1.2006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7380    0.8583   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5579    0.2457   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9503   -0.5478    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027   -1.1529    1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.7281    0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3452    0.0522    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8687   -1.3372    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1329   -0.3411   -1.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    1.1765   -1.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    1.4756   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372    0.3712   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -1.7365    2.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1915   -1.3677    1.4824 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  1  0
  9 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
  8 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0000982 (3-Hydroxyphenylacetic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0       3.080  -3.226   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081   3.704   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415   1.394   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.747  -0.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747   1.394   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -0.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -0.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -2.456   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -2.456   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -3.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   2.164   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    5    6    7                                                  
CONECT    5    4   11                                                       
CONECT    6    4    8                                                       
CONECT    7    4    9                                                       
CONECT    8    1    6   10                                                  
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
CONECT   11    2    3    5                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
Download

3D PDB for NP0000982 (3-Hydroxyphenylacetic acid)

COMPND    HMDB0000440
HETATM    1  O1  UNL     1       1.846   1.605   1.289  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.382   0.650   0.669  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.759   0.521   0.796  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.670  -0.322  -0.165  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.224  -0.108  -0.240  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.390   0.686  -1.201  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.738   0.858  -1.236  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.558   0.246  -0.310  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.950  -0.548   0.651  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.803  -1.153   1.572  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.579  -0.728   0.693  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.345   0.052   0.135  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.869  -1.337   0.274  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.133  -0.341  -1.179  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.227   1.177  -1.937  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.232   1.476  -1.980  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.637   0.371  -0.321  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.378  -1.736   2.282  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.191  -1.368   1.482  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   17
CONECT    9   10   11   11
CONECT   10   18
CONECT   11   19
END
Download

SMILES for NP0000982 (3-Hydroxyphenylacetic acid)

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

INCHI for NP0000982 (3-Hydroxyphenylacetic acid)

InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
Download
View in JSmol
Synonyms
ValueSource
(m-Hydroxyphenyl)acetic acidChEBI
3-Hydroxybenzeneacetic acidChEBI
m-Hydroxyphenylacetic acidChEBI
(m-Hydroxyphenyl)acetateGenerator
3-HydroxybenzeneacetateGenerator
m-HydroxyphenylacetateGenerator
3-HydroxyphenylacetateGenerator
(3-Hydroxy-phenyl)-acetateHMDB
(3-Hydroxy-phenyl)-acetic acidHMDB
3-Hydroxy-benzeneacetateHMDB
3-Hydroxy-benzeneacetic acidHMDB
Meta-hydroxyphenylacetic acidHMDB
3'-Hydroxyphenylacetic acidHMDB
2-(3-Hydroxyphenyl)acetic acidHMDB
3-Hydroxyphenylacetic acidKEGG
3-Hydroxyphenylethanoic acid
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name2-(3-hydroxyphenyl)acetic acid
Traditional Name3-hydroxyphenylacetic acid
CAS Registry Number621-37-4
SMILES
OC(=O)CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyFVMDYYGIDFPZAX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-26View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-26View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-26View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-26View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-01-26View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 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 Available2021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Ginkgo bilobaLOTUS Database
Homo sapiensLOTUS Database
Thanatephorus cucumerisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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 Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP0.85Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility6.98 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
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000440
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022047
KNApSAcK IDNot Available
Chemspider ID11624
KEGG Compound IDC05593
BioCyc ID3-HYDROXYPHENYLACETATE
BiGG IDNot Available
Wikipedia Link4-Hydroxyphenylacetic acid
METLIN ID5429
PubChem Compound12122
PDB IDNot Available
ChEBI ID17445
Good Scents IDrw1190711
References
General References
  1. 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 ]
  2. Davis BA, Durden DA, Boulton AA: Plasma concentrations of p- and m-hydroxyphenylacetic acid and phenylacetic acid in humans: gas chromatographic--high-resolution mass spectrometric analysis. J Chromatogr. 1982 Jul 9;230(2):219-30. [PubMed:7107773 ]
  3. Davis BA, Boulton AA: Longitudinal urinary excretion of some "trace" acids in a human male. J Chromatogr. 1981 Feb 13;222(2):161-9. [PubMed:7251734 ]
  4. Nahmias C, Wahl LM, Amano S, Asselin MC, Chirakal R: Equilibration of 6-[18F]fluoro-L-m-tyrosine between plasma and erythrocytes. J Nucl Med. 2000 Oct;41(10):1636-41. [PubMed:11037992 ]
  5. Baba S, Furuta T, Horie M, Nakagawa H: Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans. J Pharm Sci. 1981 Jul;70(7):780-2. [PubMed:7264927 ]
  6. Konishi Y: Transepithelial transport of microbial metabolites of quercetin in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2005 Feb 9;53(3):601-7. [PubMed:15686408 ]