Np mrd loader

Showing NP-Card for m-Toluic acid (NP0002789)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2020-11-23 19:40:29 UTC
Updated at2021-08-19 23:59:23 UTC
NP-MRD IDNP0002789
Secondary Accession NumbersNone
Natural Product Identification
Common Namem-Toluic acid
Provided ByBMRBBMRB logo
DescriptionM-toluic Acid, also known as 3-toluate or b-bethylbenzoate, 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. M-toluic Acid exists in all living organisms, ranging from bacteria to humans. M-toluic Acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. m-Toluic acid was first documented in 2001 (PMID: 11339298). Based on a literature review a small amount of articles have been published on M-toluic Acid (PMID: 11470206) (PMID: 22451532).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002789 (m-Toluic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.4178   -1.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -0.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    1.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763    2.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8601    1.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038    0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6401   -0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7327    0.8359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838   -1.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111   -0.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4455   -0.2898    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -2.4751    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104   -2.4101    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1052    1.5377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    3.5931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    2.7284    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -2.0843    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -2.2472    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  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10  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
  9 17  1  0
 10 18  1  0
M  END
Download

3D MOL for NP0002789 (m-Toluic acid)

NP0002789
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.5528   -0.4811    0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784    0.0516    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523    1.2737   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    1.7000   -0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    0.9651   -0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1008   -0.2550   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105   -1.0660    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2800   -2.1674    0.6958 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5150   -0.6013   -0.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1173   -0.6825    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4038    0.1274    0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -0.5652    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -1.5277    0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593    1.8598   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430    2.6737   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566    1.3313   -1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8031   -0.9908   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -1.6457    0.9494 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  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10  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
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0002789 (m-Toluic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.4178   -1.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3252   -0.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    1.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5763    2.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8601    1.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038    0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6401   -0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7327    0.8359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838   -1.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111   -0.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4455   -0.2898    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -2.4751    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104   -2.4101    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1052    1.5377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    3.5931    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527    2.7284    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201   -2.0843    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -2.2472    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  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10  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
  9 17  1  0
 10 18  1  0
M  END
> <DATABASE_ID>
NP0002789

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
GPSDUZXPYCFOSQ-UHFFFAOYSA-N

> <FORMULA>
C8H8O2

> <MOLECULAR_WEIGHT>
136.15

> <EXACT_MASS>
136.052429498

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.109789515611823

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylbenzoic acid

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.1442501133333334

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.076520131112524

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.3554

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
toluic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002789 (m-Toluic acid)

NP0002789
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.5528   -0.4811    0.8759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784    0.0516    0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523    1.2737   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375    1.7000   -0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171    0.9651   -0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1008   -0.2550   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105   -1.0660    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2800   -2.1674    0.6958 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5150   -0.6013   -0.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1173   -0.6825    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4038    0.1274    0.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -0.5652    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -1.5277    0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1593    1.8598   -0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0430    2.6737   -1.3253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566    1.3313   -1.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8031   -0.9908   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -1.6457    0.9494 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  1  0
  7  8  2  0
  7  9  1  0
  6 10  2  0
 10  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
  9 17  1  0
 10 18  1  0
M  END
Download

PDB for NP0002789 (m-Toluic acid)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.770   4.001   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.080   2.667   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    6    7                                                       
CONECT    6    1    3    5                                                  
CONECT    7    4    5    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
Download

3D PDB for NP0002789 (m-Toluic acid)

COMPND    NP0002789
HETATM    1  C1  UNL     1      -2.553  -0.481   0.876  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.278   0.052   0.317  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.252   1.274  -0.327  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.038   1.700  -0.817  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.117   0.965  -0.687  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.101  -0.255  -0.045  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.311  -1.066   0.113  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.280  -2.167   0.696  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.515  -0.601  -0.395  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.117  -0.683   0.446  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.404   0.127   0.529  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.510  -0.565   1.984  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.713  -1.528   0.499  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.159   1.860  -0.435  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.043   2.674  -1.325  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.057   1.331  -1.085  1.00  0.00           H  
HETATM   17  H7  UNL     1       3.803  -0.991  -1.295  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.116  -1.646   0.949  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3   10
CONECT    3    4   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7   10   10
CONECT    7    8    8    9
CONECT    9   17
CONECT   10   18
END
Download

SMILES for NP0002789 (m-Toluic acid)

CC1=CC(=CC=C1)C(O)=O
Download

INCHI for NP0002789 (m-Toluic acid)

InChI=1S/C8H8O2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3,(H,9,10)
Download
View in JSmol
Synonyms
ValueSource
3-Toluic acidChEBI
beta-Bethylbenzoic acidChEBI
beta-Methylbenzoic acidChEBI
m-Toluylic acidChEBI
Meta-toluic acidChEBI
3-ToluateGenerator
b-BethylbenzoateGenerator
b-Bethylbenzoic acidGenerator
beta-BethylbenzoateGenerator
Β-bethylbenzoateGenerator
Β-bethylbenzoic acidGenerator
b-MethylbenzoateGenerator
b-Methylbenzoic acidGenerator
beta-MethylbenzoateGenerator
Β-methylbenzoateGenerator
Β-methylbenzoic acidGenerator
m-ToluylateGenerator
Meta-toluateGenerator
m-ToluateGenerator
3-Toluic acid, cadmium saltHMDB
3-Toluic acid, zinc saltHMDB
3-Toluic acid, barium saltHMDB
Chemical FormulaC8H8O2
Average Mass136.1500 Da
Monoisotopic Mass136.05243 Da
IUPAC Name3-methylbenzoic acid
Traditional Nametoluic acid
CAS Registry NumberNot Available
SMILES
CC1=CC(=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O2/c1-6-3-2-4-7(5-6)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyGPSDUZXPYCFOSQ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point232.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point266.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.770 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.08ALOGPS
logP2.14ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.36 m³·mol⁻¹ChemAxon
Polarizability14.11 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0062810
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7140
KEGG Compound IDC07211
BioCyc IDCPD-8775
BiGG IDNot Available
Wikipedia LinkM-Toluic_acid
METLIN IDNot Available
PubChem Compound7418
PDB IDNot Available
ChEBI ID10589
Good Scents IDrw1389521
References
General References
  1. Abu-Qare AW, Abou-Donia MB: Development of a high-performance liquid chromatographic method for the quantification of chlorpyrifos, pyridostigmine bromide, N,N-diethyl-m-toluamide and their metabolites in rat plasma and urine. J Chromatogr B Biomed Sci Appl. 2001 Apr 25;754(2):533-8. doi: 10.1016/s0378-4347(01)00028-7. [PubMed:11339298 ]
  2. Abu-Qare AW, Abou-Donia MB: Simultaneous determination of malathion, permethrin, DEET (N,N-diethyl-m-toluamide), and their metabolites in rat plasma and urine using high performance liquid chromatography. J Pharm Biomed Anal. 2001 Sep;26(2):291-9. doi: 10.1016/s0731-7085(01)00407-1. [PubMed:11470206 ]
  3. Yuan N, Qiao JQ, Lian HZ: Simultaneous determination of nine related substances in p-phthalic acid residue by RP-HPLC. J Chromatogr Sci. 2012 May;50(5):410-3. doi: 10.1093/chromsci/bms018. Epub 2012 Mar 26. [PubMed:22451532 ]