Np mrd loader

Showing NP-Card for 3-Methylcatechol (NP0002702)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2020-11-23 19:38:19 UTC
Updated at2021-08-19 23:59:15 UTC
NP-MRD IDNP0002702
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methylcatechol
Provided ByBMRBBMRB logo
Description3-Methylcatechol, also known as 2,3-toluenediol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3-Methylcatechol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3-Methylcatechol is found in Apis cerana and Verbascum lychnitis. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on 3-Methylcatechol (PMID: 20582618) (PMID: 22854893) (PMID: 23250222) (PMID: 32168145) (PMID: 31850419) (PMID: 31811044).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002702 (3-Methylcatechol)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.2500   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -1.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500    2.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    2.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    1.1179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -1.8821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -0.3821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -2.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -2.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500   -0.3821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    3.5150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    2.2160    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
  6  8  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  9 17  1  0
M  END
Download

3D MOL for NP0002702 (3-Methylcatechol)

NP0002702
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.2555    0.0578   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.2323   -0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -1.5441   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -1.8309   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522   -0.8185   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    0.4900    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3606    1.4829    0.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958    0.8083    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4330    2.0747    0.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829    0.4028   -1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565   -0.8497    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5539    0.8374    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449   -2.3459   -0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -2.8658   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9217   -1.0106    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885    2.4443    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    2.8996    0.4301 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
  6  8  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0002702 (3-Methylcatechol)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.2500   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -1.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500    2.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    2.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    1.1179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500   -1.8821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -0.3821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -2.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -2.9801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7500   -0.3821    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    3.5150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    2.2160    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
  6  8  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  1
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  9 17  1  0
M  END
> <DATABASE_ID>
NP0002702

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
PGSWEKYNAOWQDF-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.1372

> <EXACT_MASS>
124.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.727085176271174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.8795365619999997

> <ALOGPS_LOGS>
-0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.04231581149143

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.594384881130571

> <JCHEM_PKA_STRONGEST_BASIC>
-6.26938194286343

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
35.061

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylcatechol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002702 (3-Methylcatechol)

NP0002702
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.2555    0.0578   -0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.2323   -0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4264   -1.5441   -0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -1.8309   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522   -0.8185   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    0.4900    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3606    1.4829    0.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958    0.8083    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4330    2.0747    0.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829    0.4028   -1.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8565   -0.8497    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5539    0.8374    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449   -2.3459   -0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -2.8658   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9217   -1.0106    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885    2.4443    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    2.8996    0.4301 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
  6  8  2  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  9 17  1  0
M  END
Download

PDB for NP0002702 (3-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    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    1    3    7                                                  
CONECT    6    4    7    8                                                  
CONECT    7    5    6    9                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0002702 (3-Methylcatechol)

COMPND    NP0002702
HETATM    1  C1  UNL     1       2.255   0.058  -0.111  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.810  -0.232  -0.076  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.426  -1.544  -0.246  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.928  -1.831  -0.216  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.852  -0.818  -0.019  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.418   0.490   0.148  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.361   1.483   0.343  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.096   0.808   0.124  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.433   2.075   0.280  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.583   0.403  -1.123  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.856  -0.850   0.108  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.554   0.837   0.630  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.145  -2.346  -0.401  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.272  -2.866  -0.348  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.922  -1.011   0.010  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.089   2.444   0.468  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.126   2.900   0.430  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    8
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    8    8
CONECT    7   16
CONECT    8    9
CONECT    9   17
END
Download

SMILES for NP0002702 (3-Methylcatechol)

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

INCHI for NP0002702 (3-Methylcatechol)

InChI=1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3
Download
View in JSmol
Synonyms
ValueSource
2,3-DihydroxytolueneChEBI
2,3-ToluenediolHMDB
3-MethylcatecholKEGG
Chemical FormulaC7H8O2
Average Mass124.1372 Da
Monoisotopic Mass124.05243 Da
IUPAC Name3-methylbenzene-1,2-diol
Traditional Name3-methylcatechol
CAS Registry NumberNot Available
SMILES
CC1=C(O)C(O)=CC=C1
InChI Identifier
InChI=1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3
InChI KeyPGSWEKYNAOWQDF-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
Apis ceranaLOTUS Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Verbascum lychnitisLOTUS Database
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
  • O-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
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point68.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point241.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility16480 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.340 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.03ALOGPS
logP1.88ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)9.59ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.06 m³·mol⁻¹ChemAxon
Polarizability12.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0301753
DrugBank IDDB03454
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000357
KNApSAcK IDNot Available
Chemspider ID333
KEGG Compound IDC02923
BioCyc IDCPD-111
BiGG IDNot Available
Wikipedia Link3-Methylcatechol
METLIN IDNot Available
PubChem Compound340
PDB IDNot Available
ChEBI ID18404
Good Scents IDrw1192001
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. Mulla SI, Hoskeri RS, Shouche YS, Ninnekar HZ: Biodegradation of 2-nitrotoluene by Micrococcus sp. strain SMN-1. Biodegradation. 2011 Feb;22(1):95-102. doi: 10.1007/s10532-010-9379-3. Epub 2010 Jun 27. [PubMed:20582618 ]
  3. Ma F, Shi SN, Sun TH, Li A, Zhou JT, Qu YY: Biotransformation of benzene and toluene to catechols by phenol hydroxylase from Arthrobacter sp. W1. Appl Microbiol Biotechnol. 2013 Jun;97(11):5097-103. doi: 10.1007/s00253-012-4301-z. Epub 2012 Aug 2. [PubMed:22854893 ]
  4. Tian XJ, Liu XY, Liu H, Wang SJ, Zhou NY: Biodegradation of 3-nitrotoluene by Rhodococcus sp. strain ZWL3NT. Appl Microbiol Biotechnol. 2013 Oct;97(20):9217-23. doi: 10.1007/s00253-012-4619-6. Epub 2012 Dec 19. [PubMed:23250222 ]
  5. Zhang AJ, Aschenbeck KA, Law BF, B'Hymer C, Siegel PD, Hylwa SA: Urushiol Compounds Detected in Toxicodendron-Labeled Consumer Products Using Mass Spectrometry. Dermatitis. 2020 Mar/Apr;31(2):134-139. doi: 10.1097/DER.0000000000000544. [PubMed:32168145 ]
  6. Kroflic A, Schaefer T, Hus M, Phuoc Le H, Otto T, Herrmann H: OH radicals reactivity towards phenol-related pollutants in water: temperature dependence of the rate constants and novel insights into the [OH-phenol] adduct formation. Phys Chem Chem Phys. 2020 Jan 21;22(3):1324-1332. doi: 10.1039/c9cp05533a. Epub 2019 Dec 18. [PubMed:31850419 ]
  7. Gao YZ, Liu XY, Liu H, Guo Y, Zhou NY: A Bph-Like Nitroarene Dioxygenase Catalyzes the Conversion of 3-Nitrotoluene to 3-Methylcatechol by Rhodococcus sp. Strain ZWL3NT. Appl Environ Microbiol. 2020 Feb 3;86(4). pii: AEM.02517-19. doi: 10.1128/AEM.02517-19. Print 2020 Feb 3. [PubMed:31811044 ]