Showing NP-Card for 4-Methylcatechol (NP0000415)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:40:01 UTC
NP-MRD IDNP0000415
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Methylcatechol
Description4-Methylcatechol, also known as homocatechol or toluene-3,4-diol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Outside of the human body, 4-Methylcatechol is found, on average, in the highest concentration within a few different foods such as coffee and cocoa powders and in a lower concentration in beers. 4-Methylcatechol has also been detected, but not quantified in eggplants. This could make 4-methylcatechol a potential biomarker for the consumption of these foods. Recent studies have suggested that a lack of brain-derived neurotrophic factor (BDNF) in the limbic system may cause neuropathic pain (PMID: 22198556 ). It is both a substrate and a suicide inhibitor of catechol 2,3-dioxygenase (PMID: 15006807 ). 4-Methylcatechol is a metabolite of homoprotocatechuic acid (PMID: 4974346 ). 4-Methylcatechol is known to induce the production of BDNF.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000415 (4-Methylcatechol)

  Mrv1652304272019022D          

  9  9  0  0  0  0            999 V2000
    0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for NP0000415 (4-Methylcatechol)

HMDB0000873
     RDKit          3D
4-Methylcatechol
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.5524   -0.0888   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456   -0.1512    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.3767    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.3862    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652   -0.2169    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612   -0.2395    0.0573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0361    0.9980   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944    2.1753   -0.2701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.0199   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    0.4194   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -1.0895    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    0.5875    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -2.2641    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -2.3327    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547   -1.1052    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229    3.0619   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    1.9890   -0.2634 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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for NP0000415 (4-Methylcatechol)

  Mrv1652304272019022D          

  9  9  0  0  0  0            999 V2000
    0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000415

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3

> <INCHI_KEY>
ZBCATMYQYDCTIZ-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.1372

> <EXACT_MASS>
124.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.819775304884702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylbenzene-1,2-diol

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.8795365619999997

> <ALOGPS_LOGS>
-0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.01183434905554

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.552176595160123

> <JCHEM_PKA_STRONGEST_BASIC>
-6.244242730605078

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
35.06099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methyl-1,2-benzenediol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000415 (4-Methylcatechol)

HMDB0000873
     RDKit          3D
4-Methylcatechol
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.5524   -0.0888   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456   -0.1512    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.3767    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.3862    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652   -0.2169    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612   -0.2395    0.0573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0361    0.9980   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944    2.1753   -0.2701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.0199   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    0.4194   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -1.0895    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    0.5875    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -2.2641    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -2.3327    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547   -1.1052    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229    3.0619   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    1.9890   -0.2634 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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for NP0000415 (4-Methylcatechol)

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       0.770   1.334   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      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4    5    7                                                       
CONECT    5    1    2    4                                                  
CONECT    6    3    7    8                                                  
CONECT    7    4    6    9                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0000415 (4-Methylcatechol)

COMPND    HMDB0000873
HETATM    1  C1  UNL     1       2.552  -0.089  -0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.046  -0.151   0.018  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.436  -1.377   0.183  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.944  -1.386   0.194  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.665  -0.217   0.045  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.061  -0.240   0.057  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.036   0.998  -0.120  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.794   2.175  -0.270  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.340   1.020  -0.132  1.00  0.00           C  
HETATM   10  H1  UNL     1       2.796   0.419  -0.975  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.987  -1.090   0.046  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.833   0.587   0.814  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.037  -2.264   0.296  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.466  -2.333   0.323  1.00  0.00           H  
HETATM   15  H6  UNL     1      -3.555  -1.105   0.175  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.323   3.062  -0.390  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.817   1.989  -0.263  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    9
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6    7
CONECT    6   15
CONECT    7    8    9    9
CONECT    8   16
CONECT    9   17
END
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SMILES for NP0000415 (4-Methylcatechol)

CC1=CC(O)=C(O)C=C1
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INCHI for NP0000415 (4-Methylcatechol)

InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
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Synonyms
ValueSource
1,2-Dihydroxy-4-methylbenzeneChEBI
2-Hydroxy-4-methylphenolChEBI
3,4-DihydroxytolueneChEBI
4-Methyl-1,2-benzenediolChEBI
4-Methyl-1,2-dihydroxybenzeneChEBI
4-MethylpyrocatecholChEBI
HomocatecholChEBI
HomopyrocatecholChEBI
p-MethylcatecholChEBI
p-MethylpyrocatecholChEBI
Toluene-3,4-diolChEBI
1-Methyl-3,4-dihydroxybenzeneHMDB
4-Methyl-pyrocatecholHMDB
4-MethylcateholHMDB
4-MetylcatecholHMDB
5-MethylcatecholHMDB
Chemical FormulaC7H8O2
Average Mass124.1372 Da
Monoisotopic Mass124.05243 Da
IUPAC Name4-methylbenzene-1,2-diol
Traditional Name4-methyl-1,2-benzenediol
CAS Registry Number452-86-8
SMILES
CC1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
InChI KeyZBCATMYQYDCTIZ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • P-cresol
  • M-cresol
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling Point247.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility24900 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.37Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility37.9 g/LALOGPS
logP1.02ALOGPS
logP1.88ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)9.55ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.06 m³·mol⁻¹ChemAxon
Polarizability12.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000873
DrugBank IDDB04120
Phenol Explorer Compound ID704
FoodDB IDFDB008861
KNApSAcK IDC00002660
Chemspider ID9564
KEGG Compound IDC06730
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methylcatechol
METLIN ID5834
PubChem Compound9958
PDB IDNot Available
ChEBI ID17254
Good Scents IDrw1205021
References
General References