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Showing metabocard for 3-Methoxyphenylacetic acid (HMDB0059969)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-04-09 21:16:51 UTC
Update Date2023-02-21 17:29:39 UTC
HMDB IDHMDB0059969
Secondary Accession Numbers
  • HMDB59969
Metabolite Identification
Common Name3-Methoxyphenylacetic acid
Description3-Methoxyphenylacetic acid, also known as m-Methoxyphenylacetic acid (m-OMePAA), a derivative of m-hydroxyphenylacetic acid (m-OHPAA) having the same chemical composition as that of the phytotoxic compound produced in culture by Rhizoctonia solani, a fungal pathogen of soybean. That phytotoxic compound reduced growth and symbiotic N2-fixation activity of Tracy soybeans in soil. The data indicate that phytotoxic compounds of R. solani are involved in nodule impairment and reduced N2-fixation in soybean (R. G. Orellana, and N. B. Mandava (1983) m-Hydroxyphenylacetic and m-Methoxyphenylacetic Acids of Rhizoctonia solani: Their Effect on Specific Root-Nodule Activity and Histopathology in Soybean. Journal of Phytopathology. Volume 107, Issue 2, pages 159167, June 1983).
Structure
Data?1677000579
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059969 (3-Methoxyphenylacetic acid)

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011272D          

 12 12  0  0  0  0            999 V2000
    5.9238   -2.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0988   -2.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864   -2.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0988   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864   -0.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -0.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6284   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -2.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -2.0844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6284   -2.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -2.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0059969 (3-Methoxyphenylacetic acid)

HMDB0059969
     RDKit          3D
3-Methoxyphenylacetic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
   -3.7444    0.8981   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    1.1986    0.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3920    0.2660    0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070   -1.0236   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735   -1.9170   -0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6978   -1.5340   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467   -0.2470    0.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3100    0.1443    0.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    0.6787   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.7631   -1.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4047    1.0865   -0.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315    0.6321    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -0.0109    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753    1.7746   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    0.7632   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -1.2819   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -2.9178   -0.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939   -2.2600   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -0.7088    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790    0.9477    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316    1.1206    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.6276    0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  8 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0059969 (3-Methoxyphenylacetic acid)

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011272D          

 12 12  0  0  0  0            999 V2000
    5.9238   -2.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0988   -2.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864   -2.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0988   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6864   -0.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -0.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6284   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159   -2.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3909   -2.0844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6284   -2.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8614   -2.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 12  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059969

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC(O)=O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c1-12-8-4-2-3-7(5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)

> <INCHI_KEY>
LEGPZHPSIPPYIO-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.732797570776736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.4533228396666666

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.11643275400136

> <JCHEM_PKA_STRONGEST_BASIC>
-4.826163508284621

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.82880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
M-methoxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0059969 (3-Methoxyphenylacetic acid)

HMDB0059969
     RDKit          3D
3-Methoxyphenylacetic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
   -3.7444    0.8981   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4224    1.1986    0.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3920    0.2660    0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070   -1.0236   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735   -1.9170   -0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6978   -1.5340   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467   -0.2470    0.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3100    0.1443    0.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    0.6787   -0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.7631   -1.4429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4047    1.0865   -0.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315    0.6321    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1475   -0.0109    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753    1.7746   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7891    0.7632   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6277   -1.2819   -0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -2.9178   -0.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939   -2.2600   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -0.7088    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790    0.9477    1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316    1.1206    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.6276    0.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  2  0
 12  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  6 18  1  0
  8 19  1  0
  8 20  1  0
 11 21  1  0
 12 22  1  0
M  END
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PDB for HMDB0059969 (3-Methoxyphenylacetic acid)

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  C   UNK     0      11.058  -5.219   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.518  -5.219   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.748  -3.891   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.518  -2.554   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.748  -1.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.208  -1.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.446  -2.554   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.906  -2.554   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.136  -3.891   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.596  -3.891   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.906  -5.219   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.208  -3.891   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3    7                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0059969 (3-Methoxyphenylacetic acid)

COMPND    HMDB0059969
HETATM    1  C1  UNL     1      -3.744   0.898  -0.267  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.422   1.199   0.110  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.392   0.266   0.052  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.607  -1.024  -0.384  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.574  -1.917  -0.429  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.698  -1.534  -0.038  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.947  -0.247   0.404  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.310   0.144   0.817  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.110   0.679  -0.298  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.624   0.763  -1.443  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.405   1.087  -0.067  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.131   0.632   0.435  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.148  -0.011   0.192  1.00  0.00           H  
HETATM   14  H2  UNL     1      -4.375   1.775  -0.002  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.789   0.763  -1.369  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.628  -1.282  -0.683  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.795  -2.918  -0.779  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.494  -2.260  -0.085  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.832  -0.709   1.308  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.279   0.948   1.608  1.00  0.00           H  
HETATM   21  H9  UNL     1       4.832   1.121   0.849  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.076   1.628   0.780  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   16
CONECT    5    6    6   17
CONECT    6    7   18
CONECT    7    8   12   12
CONECT    8    9   19   20
CONECT    9   10   10   11
CONECT   11   21
CONECT   12   22
END
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SMILES for HMDB0059969 (3-Methoxyphenylacetic acid)

COC1=CC(CC(O)=O)=CC=C1
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INCHI for HMDB0059969 (3-Methoxyphenylacetic acid)

InChI=1S/C9H10O3/c1-12-8-4-2-3-7(5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H10O3
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
IUPAC Name2-(3-methoxyphenyl)acetic acid
Traditional NameM-methoxyphenylacetic acid
CAS Registry Number1798-09-0
SMILES
COC1=CC(CC(O)=O)=CC=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-8-4-2-3-7(5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChI KeyLEGPZHPSIPPYIO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
Substituents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.549 +/- 0.125 umol/mmol creatinineAdult (>18 years old)MaleNormal 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15719
PDB IDNot Available
ChEBI IDNot Available
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. Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]