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Showing NP-Card for o-Toluic acid (NP0002792)

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Record Information
Version1.0
Created at2020-11-23 19:40:34 UTC
Updated at2021-08-12 19:52:09 UTC
NP-MRD IDNP0002792
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-Toluic acid
Provided ByBMRBBMRB logo
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 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. o-Toluic acid is found in Arabidopsis thaliana and Homo sapiens. It was first documented in 2005 (PMID: 16012080). Based on a literature review a small amount of articles have been published on 2-Methylbenzoic acid (PMID: 17984079) (PMID: 28342601) (PMID: 18215358) (PMID: 21793062).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002792 (o-Toluic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.2416   -1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481   -0.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290   -0.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389    1.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    1.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    2.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154    0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1502   -0.4774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3330   -2.8643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351   -2.5795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -2.8294    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126   -1.0122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324    1.9636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    3.1222    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1990    0.9756    0.0000 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  6
  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
Download

3D MOL for NP0002792 (o-Toluic acid)

NP0002792
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.0605    1.8542   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    0.7955   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256    1.1940   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.2264    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708   -1.1168    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6385   -1.4699    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -0.5278   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818   -0.9065   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6858   -0.0540   -0.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1325   -2.2353    0.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    1.8733    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    2.8753   -0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290    1.7803   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018    2.2532   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425    0.5577    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -1.8752    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3048   -2.5061    0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2551   -2.7183    0.8864 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
Download

3D SDF for NP0002792 (o-Toluic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.2416   -1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481   -0.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290   -0.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389    1.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6219    1.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8120    2.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8154    0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1502   -0.4774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3330   -2.8643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351   -2.5795    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256   -2.8294    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126   -1.0122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5324    1.9636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651    3.1222    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1990    0.9756    0.0000 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  6
  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
> <DATABASE_ID>
NP0002792

> <DATABASE_NAME>
NP-MRD

> <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 NP0002792 (o-Toluic acid)

NP0002792
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.0605    1.8542   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    0.7955   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256    1.1940   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    0.2264    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9708   -1.1168    0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6385   -1.4699    0.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -0.5278   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7818   -0.9065   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6858   -0.0540   -0.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1325   -2.2353    0.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    1.8733    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    2.8753   -0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290    1.7803   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6018    2.2532   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425    0.5577    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7291   -1.8752    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3048   -2.5061    0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2551   -2.7183    0.8864 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
Download

PDB for NP0002792 (o-Toluic 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 NP0002792 (o-Toluic acid)

COMPND    NP0002792
HETATM    1  C1  UNL     1      -1.061   1.854  -0.168  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.010   0.795  -0.088  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.326   1.194  -0.072  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.314   0.226   0.001  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.971  -1.117   0.057  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.638  -1.470   0.039  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.390  -0.528  -0.035  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.782  -0.906  -0.053  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.686  -0.054  -0.119  1.00  0.00           O  
HETATM   10  O2  UNL     1      -2.132  -2.235   0.002  1.00  0.00           O  
HETATM   11  H1  UNL     1      -1.698   1.873   0.750  1.00  0.00           H  
HETATM   12  H2  UNL     1      -0.584   2.875  -0.188  1.00  0.00           H  
HETATM   13  H3  UNL     1      -1.629   1.780  -1.102  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.602   2.253  -0.116  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.342   0.558   0.013  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.729  -1.875   0.114  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.305  -2.506   0.080  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.255  -2.718   0.886  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 NP0002792 (o-Toluic acid)

CC1=C(C=CC=C1)C(O)=O
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INCHI for NP0002792 (o-Toluic 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 JSmol
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-Methylbenzoic acidChEBI
2-Toluic acid, cadmium saltMeSH, HMDB
2-Toluic acid, sodium salt, 11C-labeledMeSH, HMDB
Chemical FormulaC8H8O2
Average Mass136.1479 Da
Monoisotopic Mass136.05243 Da
IUPAC Name2-methylbenzoic acid
Traditional Nameo-toluic acid
CAS Registry NumberNot Available
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaLOTUS Database
Homo sapiensLOTUS Database
Species Where Detected
Species NameSourceReference
Hypoxylon rubiginosumKNApSAcK Database
Lobaria yunnanensisKNApSAcK Database
Penicillium cyclopiumKNApSAcK Database
Stereum hirsutumKNApSAcK Database
Umbilicaria hypococcineaKNApSAcK Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0002340
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
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