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Showing NP-Card for 3-Methylphenylacetic acid (NP0000945)

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Record Information
Version2.0
Created at2006-05-22 14:17:42 UTC
Updated at2021-10-07 20:40:46 UTC
NP-MRD IDNP0000945
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methylphenylacetic acid
Description3-Methylphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 3-methylphenyl group. It has a role as a fungal xenobiotic metabolite. It is a monocarboxylic acid and a member of benzenes. It derives from an acetic acid. 3-Methylphenylacetic acid belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000945 (3-Methylphenylacetic acid)


  Mrv1652305261923582D          

 11 11  0  0  0  0            999 V2000
   27.0368   -3.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7513   -4.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3224   -4.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8933   -7.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0368   -4.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3224   -5.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6078   -7.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6078   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0368   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3224   -7.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0368   -7.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  5  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0000945 (3-Methylphenylacetic acid)

HMDB0002222
     RDKit          3D
3-Methylphenylacetic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.7478   -1.1572    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -0.2414    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763    1.0382   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046    1.8628   -0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    1.4191   -0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505    0.1300   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473   -0.3328   -0.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7716   -0.0388    0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375    0.5312    1.4529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -0.3545    0.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -0.6704    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6289   -0.6200    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144   -1.7011    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -1.9185    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    1.3800    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589    2.8649   -0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662    2.0599   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353    0.1268   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -1.4497   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597   -1.2652    0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -1.6633    0.3430 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  1  0
  8  9  2  0
  8 10  1  0
  6 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0000945 (3-Methylphenylacetic acid)


  Mrv1652305261923582D          

 11 11  0  0  0  0            999 V2000
   27.0368   -3.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7513   -4.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3224   -4.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8933   -7.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0368   -4.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3224   -5.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6078   -7.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6078   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0368   -6.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3224   -7.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0368   -7.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  5  2  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000945

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c1-7-3-2-4-8(5-7)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)

> <INCHI_KEY>
GJMPSRSMBJLKKB-UHFFFAOYSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.932781072003067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-methylphenyl)acetic acid

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.1244154946666667

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.690378075607591

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
42.406800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylphenylacetic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000945 (3-Methylphenylacetic acid)

HMDB0002222
     RDKit          3D
3-Methylphenylacetic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
   -2.7478   -1.1572    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7262   -0.2414    0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0763    1.0382   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046    1.8628   -0.6957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867    1.4191   -0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505    0.1300   -0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9473   -0.3328   -0.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7716   -0.0388    0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375    0.5312    1.4529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1162   -0.3545    0.5779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -0.6704    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6289   -0.6200    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144   -1.7011    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9723   -1.9185    0.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896    1.3800    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3589    2.8649   -0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662    2.0599   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353    0.1268   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -1.4497   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4597   -1.2652    0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -1.6633    0.3430 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  1  0
  8  9  2  0
  8 10  1  0
  6 11  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

PDB for NP0000945 (3-Methylphenylacetic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      50.469  -6.911   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      51.802  -9.221   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      49.135  -9.221   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      46.467 -13.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      50.469  -8.451   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.135 -10.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.801 -13.071   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.801 -11.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      50.469 -11.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      49.135 -13.841   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.469 -13.071   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    5    6                                                       
CONECT    4    7                                                            
CONECT    5    1    2    3                                                  
CONECT    6    3    8    9                                                  
CONECT    7    4    8   10                                                  
CONECT    8    6    7                                                       
CONECT    9    6   11                                                       
CONECT   10    7   11                                                       
CONECT   11    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000945 (3-Methylphenylacetic acid)

COMPND    HMDB0002222
HETATM    1  C1  UNL     1      -2.748  -1.157   0.844  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.726  -0.241   0.238  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.076   1.038  -0.136  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.105   1.863  -0.696  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.187   1.419  -0.877  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.551   0.130  -0.503  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.947  -0.333  -0.705  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.772  -0.039   0.475  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.238   0.531   1.453  1.00  0.00           O  
HETATM   10  O2  UNL     1       4.116  -0.355   0.578  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.433  -0.670   0.051  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.629  -0.620   1.187  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.214  -1.701   1.653  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.972  -1.919   0.064  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.090   1.380   0.008  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.359   2.865  -0.994  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.966   2.060  -1.318  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.335   0.127  -1.634  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.950  -1.450  -0.866  1.00  0.00           H  
HETATM   20  H9  UNL     1       4.460  -1.265   0.836  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.168  -1.663   0.343  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5    5   16
CONECT    5    6   17
CONECT    6    7   11   11
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   21
END
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SMILES for NP0000945 (3-Methylphenylacetic acid)

CC1=CC(CC(O)=O)=CC=C1
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INCHI for NP0000945 (3-Methylphenylacetic acid)

InChI=1S/C9H10O2/c1-7-3-2-4-8(5-7)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
3-Tolylacetic acidChEBI
m-Methylphenylacetic acidChEBI
m-Tolylacetic acidChEBI
3-TolylacetateGenerator
m-MethylphenylacetateGenerator
m-TolylacetateGenerator
3-MethylphenylacetateGenerator
(3-Methylphenyl)acetateHMDB
(3-Methylphenyl)acetic acidHMDB
Chemical FormulaC9H10O2
Average Mass150.1745 Da
Monoisotopic Mass150.06808 Da
IUPAC Name2-(3-methylphenyl)acetic acid
Traditional Name3-methylphenylacetic acid
CAS Registry Number621-36-3
SMILES
CC1=CC(CC(O)=O)=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c1-7-3-2-4-8(5-7)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)
InChI KeyGJMPSRSMBJLKKB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-09-05View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-11View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentToluenes
Alternative Parents
Substituents
  • Toluene
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point62 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4065 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.95Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility1.54 g/LALOGPS
logP2.11ALOGPS
logP2.12ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.41 m³·mol⁻¹ChemAxon
Polarizability15.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002222
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022916
KNApSAcK IDNot Available
Chemspider ID11623
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6557
PubChem Compound12121
PDB IDNot Available
ChEBI ID88356
Good Scents IDrw1257321
References
General References
  1. de Oliveira JR, Seleghim MH, Porto AL: Biotransformation of methylphenylacetonitriles by Brazilian marine fungal strain Aspergillus sydowii CBMAI 934: eco-friendly reactions. Mar Biotechnol (NY). 2014 Apr;16(2):156-60. doi: 10.1007/s10126-013-9534-z. Epub 2013 Sep 22. [PubMed:24057165 ]