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Showing metabocard for 2-Methylbenzoic acid (HMDB0002340)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2023-02-21 17:16:21 UTC
HMDB IDHMDB0002340
Secondary Accession Numbers
  • HMDB02340
Metabolite Identification
Common Name2-Methylbenzoic acid
Description2-Methylbenzoic acid, also known as 2-toluic acid or O-methylbenzoate, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. 2-Methylbenzoic acid has been detected, but not quantified in, milk (cow). This could make 2-methylbenzoic acid a potential biomarker for the consumption of these foods. 2-Methylbenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2-Methylbenzoic acid.
Structure
Data?1676999781
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002340 (2-Methylbenzoic acid)


  Mrv1652304032018422D          

 10 10  0  0  0  0            999 V2000
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for HMDB0002340 (2-Methylbenzoic acid)

HMDB0002340
     RDKit          3D
2-Methylbenzoic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    0.9682   -1.7304    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297   -0.6637    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -1.0075   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603   -0.0644   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0478    1.2726    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    1.6202    0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929    0.6700    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872    1.0301    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846    2.2565    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    0.1403    0.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4945   -1.6775    1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -2.7194    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7383   -1.6750   -0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822   -2.0439   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4113   -0.3235   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7977    2.0522    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965    2.6553    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300    0.2080   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
 10 18  1  0
M  END
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3D SDF for HMDB0002340 (2-Methylbenzoic acid)


  Mrv1652304032018422D          

 10 10  0  0  0  0            999 V2000
    0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002340

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H,9,10)

> <INCHI_KEY>
ZWLPBLYKEWSWPD-UHFFFAOYSA-N

> <FORMULA>
C8H8O2

> <MOLECULAR_WEIGHT>
136.1479

> <EXACT_MASS>
136.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.952352341678761

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbenzoic acid

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.1442501133333334

> <ALOGPS_LOGS>
-1.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9579559636385615

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.355399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
o-toluic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0002340 (2-Methylbenzoic acid)

HMDB0002340
     RDKit          3D
2-Methylbenzoic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    0.9682   -1.7304    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297   -0.6637    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638   -1.0075   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3603   -0.0644   -0.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0478    1.2726    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    1.6202    0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929    0.6700    0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6872    1.0301    0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846    2.2565    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441    0.1403    0.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4945   -1.6775    1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687   -2.7194    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7383   -1.6750   -0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6822   -2.0439   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4113   -0.3235   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7977    2.0522    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3965    2.6553    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300    0.2080   -0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
  6 17  1  0
 10 18  1  0
M  END
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PDB for HMDB0002340 (2-Methylbenzoic acid)

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    3    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0002340 (2-Methylbenzoic acid)

COMPND    HMDB0002340
HETATM    1  C1  UNL     1       0.968  -1.730   0.147  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.030  -0.664   0.118  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.364  -1.008  -0.020  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.360  -0.064  -0.056  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.048   1.273   0.047  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.719   1.620   0.185  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.293   0.670   0.222  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.687   1.030   0.366  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.985   2.257   0.462  1.00  0.00           O  
HETATM   10  O2  UNL     1       2.744   0.140   0.408  1.00  0.00           O  
HETATM   11  H1  UNL     1       1.494  -1.677   1.142  1.00  0.00           H  
HETATM   12  H2  UNL     1       0.469  -2.719   0.157  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.738  -1.675  -0.642  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.682  -2.044  -0.107  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.411  -0.324  -0.164  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.798   2.052   0.024  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.396   2.655   0.272  1.00  0.00           H  
HETATM   18  H8  UNL     1       3.430   0.208  -0.337  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    7
CONECT    3    4   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7   17
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   18
END
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SMILES for HMDB0002340 (2-Methylbenzoic acid)

CC1=C(C=CC=C1)C(O)=O
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INCHI for HMDB0002340 (2-Methylbenzoic acid)

InChI=1S/C8H8O2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Toluic acidChEBI
O-Toluylic acidChEBI
Orthotoluic acidChEBI
O-MethylbenzoateKegg
O-Toluic acidKegg
2-ToluateGenerator
O-ToluylateGenerator
OrthotoluateGenerator
O-Methylbenzoic acidGenerator
O-ToluateGenerator
2-MethylbenzoateGenerator
2-Toluic acid, cadmium saltHMDB
2-Toluic acid, sodium salt, 11C-labeledHMDB
2-Methylbenzoic acidChEBI
Chemical FormulaC8H8O2
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
IUPAC Name2-methylbenzoic acid
Traditional Nameo-toluic acid
CAS Registry Number118-90-1
SMILES
CC1=C(C=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyZWLPBLYKEWSWPD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • Benzoyl
  • Toluene
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Point103.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.18 mg/mL at 25 °CNot Available
LogP2.46HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.02 g/LALOGPS
logP2.03ALOGPS
logP2.14ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.36 m³·mol⁻¹ChemAxon
Polarizability13.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.60631661259
DarkChem[M-H]-122.51131661259
DeepCCS[M+H]+128.03730932474
DeepCCS[M-H]-124.4230932474
DeepCCS[M-2H]-161.33130932474
DeepCCS[M+Na]+136.630932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.132859911
AllCCS[M+NH4]+131.332859911
AllCCS[M+Na]+132.532859911
AllCCS[M-H]-124.032859911
AllCCS[M+Na-2H]-125.632859911
AllCCS[M+HCOO]-127.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.4.57 minutes32390414
Predicted by Siyang on May 30, 202211.8223 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.66 minutes32390414

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methylbenzoic acidCC1=CC=CC=C1C(O)=O2172.4Standard polar33892256
2-Methylbenzoic acidCC1=CC=CC=C1C(O)=O1197.6Standard non polar33892256
2-Methylbenzoic acidCC1=CC=CC=C1C(O)=O1288.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methylbenzoic acid,1TMS,isomer #1CC1=CC=CC=C1C(=O)O[Si](C)(C)C1337.0Semi standard non polar33892256
2-Methylbenzoic acid,1TBDMS,isomer #1CC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C1558.5Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified2.8(1.0-4.2) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB098186
KNApSAcK IDC00000487
Chemspider ID8070
KEGG Compound IDC07215
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Toluic_acid
METLIN IDNot Available
PubChem Compound8373
PDB IDNot Available
ChEBI ID36632
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRen, Jun. Study on preparation of o-methylbenzoic acid from liquid-phase oxidation of o-xylene. Huagong Shikan (1997), 11(6), 19-20.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yu WY, Yang LX, Xie JS, Zhou L, Jiang XY, Zhu DX, Muramatsu M, Wang MW: Derivatives of aryl-4-guanidinomethylbenzoate and N-aryl-4-guanidinomethylbenzamide as new antibacterial agents: synthesis and bioactivity. Acta Pharmacol Sin. 2008 Feb;29(2):267-77. [PubMed:18215358 ]