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Showing NP-Card for p-Toluic acid (NP0002730)

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Record Information
Version2.0
Created at2020-11-23 19:39:01 UTC
Updated at2021-08-19 23:59:17 UTC
NP-MRD IDNP0002730
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Toluic acid
Provided ByBMRBBMRB logo
Description4-Methylbenzoic acid, also known as p-toluate or toluenecarboxylate, 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. 4-Methylbenzoic acid exists in all living organisms, ranging from bacteria to humans. 4-Methylbenzoic 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. p-Toluic acid is found in Aloe africana, Artemisia afra and Homo sapiens. p-Toluic acid was first documented in 2002 (PMID: 11876420). Based on a literature review very few articles have been published on 4-Methylbenzoic acid (PMID: 21978560).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002730 (p-Toluic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.1210   -0.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257   -0.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9797    1.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156    1.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605    0.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5064    1.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100   -0.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192   -1.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386    1.3225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035   -1.6683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6164   -0.2904    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8292    2.5347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1616    2.7698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2054   -0.8216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687   -2.4104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4221   -2.6455    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
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  1
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D MOL for NP0002730 (p-Toluic acid)

NP0002730
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.8288    0.5927   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    0.1812   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4713    1.1233    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8725    0.8382    0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.4469   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6889   -0.7901    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330   -1.9503   -0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6129    0.1459    0.3805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -1.4026   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.0865   -0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    1.4326   -0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746   -0.2307   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    1.0319    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    2.1414    0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339    1.5661    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344    1.0960    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7028   -2.4067   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283   -1.8355   -0.7141 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
  6  8  1  0
  5  9  1  0
  9 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
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

3D SDF for NP0002730 (p-Toluic acid)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -3.1210   -0.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6257   -0.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9797    1.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156    1.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605    0.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5064    1.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100   -0.9391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192   -1.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2386    1.3225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035   -1.6683    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6164   -0.2904    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8292    2.5347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1616    2.7698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2054   -0.8216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5687   -2.4104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4221   -2.6455    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
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10  2  1  0
  1 11  1  1
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
> <DATABASE_ID>
NP0002730

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
LPNBBFKOUUSUDB-UHFFFAOYSA-N

> <FORMULA>
C8H8O2

> <MOLECULAR_WEIGHT>
136.1479

> <EXACT_MASS>
136.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.148327918924418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylbenzoic acid

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.1442501133333334

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.264417343965437

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.3554

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
p-toluic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002730 (p-Toluic acid)

NP0002730
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -2.8288    0.5927   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    0.1812   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4713    1.1233    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8725    0.8382    0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -0.4469   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6889   -0.7901    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0330   -1.9503   -0.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6129    0.1459    0.3805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3439   -1.4026   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.0865   -0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    1.4326   -0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746   -0.2307   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    1.0319    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    2.1414    0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6339    1.5661    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344    1.0960    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7028   -2.4067   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283   -1.8355   -0.7141 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
  6  8  1  0
  5  9  1  0
  9 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
  8 16  1  0
  9 17  1  0
 10 18  1  0
M  END
Download

PDB for NP0002730 (p-Toluic acid)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.926   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.693  -0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.693   0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.693   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.693   2.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.926   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.314   2.311   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.314   0.001   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.080  -0.769   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.080  -2.311   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    3    8   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002730 (p-Toluic acid)

COMPND    NP0002730
HETATM    1  C1  UNL     1      -2.829   0.593  -0.056  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.410   0.181  -0.058  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.471   1.123   0.320  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.872   0.838   0.351  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.262  -0.447  -0.014  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.689  -0.790   0.006  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.033  -1.950  -0.324  1.00  0.00           O  
HETATM    8  O2  UNL     1       3.613   0.146   0.380  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.344  -1.403  -0.394  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.993  -1.087  -0.415  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.018   1.433  -0.787  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.475  -0.231  -0.364  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.110   1.032   0.941  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.750   2.141   0.612  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.634   1.566   0.646  1.00  0.00           H  
HETATM   16  H6  UNL     1       3.634   1.096   0.007  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.703  -2.407  -0.675  1.00  0.00           H  
HETATM   18  H8  UNL     1      -1.728  -1.835  -0.714  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    9
CONECT    6    7    7    8
CONECT    8   16
CONECT    9   10   10   17
CONECT   10   18
END
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SMILES for NP0002730 (p-Toluic acid)

CC1=CC=C(C=C1)C(O)=O
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INCHI for NP0002730 (p-Toluic acid)

InChI=1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10)
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View in JSmol
Synonyms
ValueSource
4-Toluic acidChEBI
Crithminic acidChEBI
p-CarboxytolueneChEBI
p-Methylbenzoic acidChEBI
p-Toluylic acidChEBI
Para-toluic acidChEBI
Toluenecarboxylic acidChEBI
p-ToluateKegg
p-Toluic acidKegg
4-ToluateGenerator
CrithminateGenerator
p-MethylbenzoateGenerator
p-ToluylateGenerator
Para-toluateGenerator
ToluenecarboxylateGenerator
4-MethylbenzoateGenerator
2420-97-5 (Cadmium salt)HMDB
4-Methyl-benzoic acidHMDB
Crithmic acidHMDB
ToluateHMDB
4-Toluic acid, calcium saltHMDB
4-Toluic acid, potassium saltHMDB
p-ToluenecarboxylateHMDB
4-Toluic acid, cadmium saltHMDB
4-Toluic acid, barium saltHMDB
4-Toluic acid, zinc saltHMDB
4-Methylbenzoic acidChEBI
Chemical FormulaC8H8O2
Average Mass136.1479 Da
Monoisotopic Mass136.05243 Da
IUPAC Name4-methylbenzoic acid
Traditional Namep-toluic acid
CAS Registry NumberNot Available
SMILES
CC1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyLPNBBFKOUUSUDB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Artemisia afraLOTUS Database
Homo sapiensLOTUS Database
Solanum tuberosumKNApSAcK 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 Solubility340 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.12ALOGPS
logP2.14ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.36 m³·mol⁻¹ChemAxon
Polarizability14.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029635
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000805
KNApSAcK IDC00055682
Chemspider ID7190
KEGG Compound IDC01454
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkP-toluic_acid
METLIN IDNot Available
PubChem Compound7470
PDB ID4MA
ChEBI ID36635
Good Scents IDrw1271561
References
General References
  1. Bramucci MG, McCutchen CM, Singh M, Thomas SM, Larsen BS, Buckholz J, Nagarajan V: Pure bacterial isolates that convert p-xylene to terephthalic acid. Appl Microbiol Biotechnol. 2002 Feb;58(2):255-9. doi: 10.1007/s00253-001-0879-2. [PubMed:11876420 ]
  2. Rajalakshmi M, Indirajith R, Palanichamy M, Gopalakrishnan R: Synthesis, growth, thermal, optical and mechanical properties of 2-Aminopyridinium 4-methylbenzoate Dihydrate. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Dec 15;84(1):43-50. doi: 10.1016/j.saa.2011.08.041. Epub 2011 Aug 31. [PubMed:21978560 ]