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Showing metabocard for 2-Methoxybenzoic acid (HMDB0032604)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:50:44 UTC
Update Date2023-02-21 17:22:27 UTC
HMDB IDHMDB0032604
Secondary Accession Numbers
  • HMDB32604
Metabolite Identification
Common Name2-Methoxybenzoic acid
Description2-Methoxybenzoic acid, also known as 2-methoxybenzoate or O-anisic acid, belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group. 2-Methoxybenzoic acid has been detected, but not quantified in, several different foods, such as sugar apples (Annona squamosa), cereals and cereal products, fruits, cowpeas (Vigna unguiculata), and other cereal product. This could make 2-methoxybenzoic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Methoxybenzoic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032604 (2-Methoxybenzoic acid)

  Mrv0541 05061306352D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
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3D MOL for HMDB0032604 (2-Methoxybenzoic acid)

HMDB0032604
     RDKit          3D
2-Methoxybenzoic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    2.1059   -1.9282    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821   -0.5782    0.2348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -0.3317    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856   -1.3518   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -1.0261   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    0.2753   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206    1.2793   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.9791   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    2.0274    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262    1.8015    0.2592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895    3.3388   -0.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940   -2.0404    0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -2.4732    1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7669   -2.4586   -0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -2.3691   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051   -1.8324   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4027    0.5007   -0.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    2.3180   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0933    3.8694    0.7396 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 11 19  1  0
M  END
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3D SDF for HMDB0032604 (2-Methoxybenzoic acid)

  Mrv0541 05061306352D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032604

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H,9,10)

> <INCHI_KEY>
ILUJQPXNXACGAN-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.78169561375502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxybenzoic acid

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.4731574583333336

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7270812043190795

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890269112323763

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
39.7774

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
o-anisic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0032604 (2-Methoxybenzoic acid)

HMDB0032604
     RDKit          3D
2-Methoxybenzoic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    2.1059   -1.9282    0.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821   -0.5782    0.2348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351   -0.3317    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5856   -1.3518   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9103   -1.0261   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    0.2753   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206    1.2793   -0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812    0.9791   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9116    2.0274    0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262    1.8015    0.2592 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895    3.3388   -0.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1940   -2.0404    0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -2.4732    1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7669   -2.4586   -0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -2.3691   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051   -1.8324   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4027    0.5007   -0.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    2.3180   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0933    3.8694    0.7396 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  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
 11 19  1  0
M  END
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PDB for HMDB0032604 (2-Methoxybenzoic acid)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    7    8                                                  
CONECT    7    5    6   11                                                  
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1    7                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0032604 (2-Methoxybenzoic acid)

COMPND    HMDB0032604
HETATM    1  C1  UNL     1       2.106  -1.928   0.326  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.682  -0.578   0.235  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.335  -0.332   0.022  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.586  -1.352  -0.102  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.910  -1.026  -0.313  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.359   0.275  -0.407  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.421   1.279  -0.280  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.081   0.979  -0.067  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.912   2.027   0.067  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.126   1.802   0.259  1.00  0.00           O  
HETATM   11  O3  UNL     1       0.490   3.339  -0.023  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.194  -2.040   0.355  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.584  -2.473   1.151  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.767  -2.459  -0.612  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.223  -2.369  -0.027  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.605  -1.832  -0.406  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.403   0.501  -0.573  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.701   2.318  -0.343  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.093   3.869   0.740  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   15
CONECT    5    6    6   16
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   19
END
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SMILES for HMDB0032604 (2-Methoxybenzoic acid)

COC1=CC=CC=C1C(O)=O
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INCHI for HMDB0032604 (2-Methoxybenzoic acid)

InChI=1S/C8H8O3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-methoxybenzoic acid
Traditional Nameo-anisic acid
CAS Registry Number579-75-9
SMILES
COC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C8H8O3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyILUJQPXNXACGAN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentO-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • O-methoxybenzoic acid or derivatives
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point106 °CNot Available
Boiling Point279.00 to 280.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility5 mg/mL at 30 °CNot Available
LogP1.59Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010544
KNApSAcK IDC00034769
Chemspider ID10892
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Methoxybenzoic_acid
METLIN IDNot Available
PubChem Compound11370
PDB IDNot Available
ChEBI ID421840
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1056551
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Methoxybenzoic acid → 3,4,5-trihydroxy-6-(2-methoxybenzoyloxy)oxane-2-carboxylic aciddetails
Enzyme Details
2. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
2-Methoxybenzoic acid → 2-{[hydroxy(2-methoxyphenyl)methylidene]amino}acetic aciddetails