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Showing metabocard for 4-Methoxyphenylacetic acid (HMDB0002072)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2023-02-21 17:16:07 UTC
HMDB IDHMDB0002072
Secondary Accession Numbers
  • HMDB02072
Metabolite Identification
Common Name4-Methoxyphenylacetic acid
Description4-methoxyphenylacetic acid is a monocarboxylic acid that is phenylacetic acid carrying a 4-methoxy substituent. It is used as an intermediate for pharmaceuticals and other organic synthesis. It has been found to inhibit the germination of cress and lettuce seeds. It has a role as a plant metabolite, a plant growth retardant and an Aspergillus metabolite. It is a monocarboxylic acid and a monomethoxybenzene. 4-Methoxyphenylacetic acid, also known as 4-methoxybenzeneacetate or 2-(p-anisyl)acetic acid, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 4-Methoxyphenylacetic acid is a 4-O-Methylated catecholamine metabolite found in normal human urine, cerebrospinal fluid and brain tissue.
Structure
Data?1676999767
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002072 (4-Methoxyphenylacetic acid)

  Mrv1652305261923592D          

 12 12  0  0  0  0            999 V2000
   25.9719   -8.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -3.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4009   -4.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -4.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -8.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -4.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -7.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -5.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for HMDB0002072 (4-Methoxyphenylacetic acid)

HMDB0002072
     RDKit          3D
4-Methoxyphenylacetic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
   -4.0110    0.1751    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478    0.7435   -0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373    0.3402   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7235    1.0646   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5995    0.7275   -0.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -0.3740   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154   -0.6608   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.0374    0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039   -0.6011    2.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8391    1.1717    0.7872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -1.0888    0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827   -0.7381    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    1.0012    0.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017   -0.3077    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5604   -0.6042    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765    1.9212   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    1.2616   -1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -0.2503   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -1.7655   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.2501    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.9371    1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8916   -1.2917    1.2175 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  2  0
  8 10  1  0
  6 11  1  0
 11 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
  7 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for HMDB0002072 (4-Methoxyphenylacetic acid)

  Mrv1652305261923592D          

 12 12  0  0  0  0            999 V2000
   25.9719   -8.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -3.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4009   -4.9387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -4.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -8.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -4.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -7.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9719   -5.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -7.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6865   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2575   -6.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002072

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
NRPFNQUDKRYCNX-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.855201156554454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.4533228396666666

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.116021917653093

> <JCHEM_PKA_STRONGEST_BASIC>
-4.824732645952242

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.8288

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxyphenylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002072 (4-Methoxyphenylacetic acid)

HMDB0002072
     RDKit          3D
4-Methoxyphenylacetic acid
 22 22  0  0  0  0  0  0  0  0999 V2000
   -4.0110    0.1751    0.6283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478    0.7435   -0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6373    0.3402   -0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7235    1.0646   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5995    0.7275   -0.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -0.3740   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5154   -0.6608   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -0.0374    0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039   -0.6011    2.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8391    1.1717    0.7872 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -1.0888    0.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1827   -0.7381    0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984    1.0012    0.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017   -0.3077    1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5604   -0.6042    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765    1.9212   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    1.2616   -1.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -0.2503   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -1.7655   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.2501    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4630   -1.9371    1.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8916   -1.2917    1.2175 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  2  0
  8 10  1  0
  6 11  1  0
 11 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
  7 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

PDB for HMDB0002072 (4-Methoxyphenylacetic 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      48.481 -15.379   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      49.815  -6.909   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      51.148  -9.219   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      48.481  -9.219   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.147 -16.149   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.815  -8.449   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.481 -13.839   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      48.481 -10.759   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.815 -13.069   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      47.147 -13.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.815 -11.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.147 -11.529   0.000  0.00  0.00           C+0
CONECT    1    5    7                                                       
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    6    8                                                       
CONECT    5    1                                                            
CONECT    6    2    3    4                                                  
CONECT    7    1    9   10                                                  
CONECT    8    4   11   12                                                  
CONECT    9    7   11                                                       
CONECT   10    7   12                                                       
CONECT   11    8    9                                                       
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0002072 (4-Methoxyphenylacetic acid)

COMPND    HMDB0002072
HETATM    1  C1  UNL     1      -4.011   0.175   0.628  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.948   0.743  -0.085  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.637   0.340  -0.101  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.724   1.065  -0.886  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.599   0.728  -0.956  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.059  -0.374  -0.225  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.515  -0.661  -0.287  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.168  -0.037   0.895  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.104  -0.601   2.011  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.839   1.172   0.787  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.178  -1.089   0.544  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.183  -0.738   0.614  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.698   1.001   0.939  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.602  -0.308   1.561  1.00  0.00           H  
HETATM   15  H3  UNL     1      -4.560  -0.604   0.081  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.076   1.921  -1.462  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.321   1.262  -1.559  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.960  -0.250  -1.212  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.629  -1.766  -0.304  1.00  0.00           H  
HETATM   20  H8  UNL     1       4.494   1.250   0.019  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.463  -1.937   1.130  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.892  -1.292   1.218  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   11
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   12   12   21
CONECT   12   22
END
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SMILES for HMDB0002072 (4-Methoxyphenylacetic acid)

COC1=CC=C(CC(O)=O)C=C1
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INCHI for HMDB0002072 (4-Methoxyphenylacetic acid)

InChI=1S/C9H10O3/c1-12-8-4-2-7(3-5-8)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-(4-methoxyphenyl)acetic acid
Traditional Name4-methoxyphenylacetic acid
CAS Registry Number104-01-8
SMILES
COC1=CC=C(CC(O)=O)C=C1
InChI Identifier
InChI=1S/C9H10O3/c1-12-8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChI KeyNRPFNQUDKRYCNX-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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point87 °CNot Available
Boiling Point138.00 to 140.00 °C. @ 3.00 mm HgThe Good Scents Company Information System
Water Solubility18 mg/mLNot Available
LogP1.42HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos137.4430932474
[M+H]+Not Available137.951http://allccs.zhulab.cn/database/detail?ID=AllCCS00000528
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral leukoplakia (OLK) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022832
KNApSAcK IDNot Available
Chemspider ID7406
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6472
PubChem Compound7690
PDB IDNot Available
ChEBI ID55501
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1204611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]