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Showing NP-Card for 3-methoxycatechol (NP0225548)

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Record Information
Version2.0
Created at2022-09-06 04:18:05 UTC
Updated at2022-09-06 04:18:05 UTC
NP-MRD IDNP0225548
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-methoxycatechol
Description3-Methoxybenzene-1,2-diol, also known as 1-O-methylpyrogallol or 2,3-dihydroxyanisole, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-methoxycatechol was first documented in 1946 (PMID: 20280766). 3-Methoxybenzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 15231803) (PMID: 2121686) (PMID: 23402862) (PMID: 24276120).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0225548 (3-methoxycatechol)


  Mrv1652308191921392D          

 10 10  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
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3D MOL for NP0225548 (3-methoxycatechol)

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3D SDF for NP0225548 (3-methoxycatechol)

  Mrv1652308191921392D          

 10 10  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O3/c1-10-6-4-2-3-5(8)7(6)9/h2-4,8-9H,1H3

> <INCHI_KEY>
LPYUENQFPVNPHY-UHFFFAOYSA-N

> <FORMULA>
C7H8O3

> <MOLECULAR_WEIGHT>
140.138

> <EXACT_MASS>
140.047344118

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.509709402304981

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.52

> <JCHEM_LOGP>
1.208443907

> <ALOGPS_LOGS>
-0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.129812802093767

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.564343786749696

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9020918663184805

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
36.483

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.70e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-benzenediol, 3-methoxy-

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0225548 (3-methoxycatechol)
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PDB for NP0225548 (3-methoxycatechol)
HEADER    PROTEIN                                 19-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-AUG-19         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    7   10                                                  
CONECT    7    5    6    9                                                  
CONECT    8    5                                                            
CONECT    9    7                                                            
CONECT   10    1    6                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0225548 (3-methoxycatechol)
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SMILES for NP0225548 (3-methoxycatechol)
COC1=CC=CC(O)=C1O
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INCHI for NP0225548 (3-methoxycatechol)
InChI=1S/C7H8O3/c1-10-6-4-2-3-5(8)7(6)9/h2-4,8-9H,1H3
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View in JSmol
Synonyms
ValueSource
1,2-Dihydroxy-3-methoxybenzeneChEBI
1-O-MethylpyrogallolChEBI
2,3-DihydroxyanisoleChEBI
3-Methoxy-O-hydroquinoneChEBI
3-MethoxypyrocatecholChEBI
6-MethoxycatecholChEBI
Pyrogallol 1-methyl etherChEBI
Pyrogallol 1-monomethyl etherChEBI
Chemical FormulaC7H8O3
Average Mass140.1380 Da
Monoisotopic Mass140.04734 Da
IUPAC Name3-methoxybenzene-1,2-diol
Traditional Name1,2-benzenediol, 3-methoxy-
CAS Registry NumberNot Available
SMILES
COC1=CC=CC(O)=C1O
InChI Identifier
InChI=1S/C7H8O3/c1-10-6-4-2-3-5(8)7(6)9/h2-4,8-9H,1H3
InChI KeyLPYUENQFPVNPHY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassMethoxyphenols  
Direct ParentMethoxyphenols  
Alternative Parents
Substituents
  • Methoxyphenol
    • 

  • Phenoxy compound
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Catechol
    • 

  • Anisole
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.52ALOGPS
logP1.21ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.48 m³·mol⁻¹ChemAxon
Polarizability13.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0125538  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB084417  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13622  
PDB IDNot Available
ChEBI ID141700  
Good Scents IDNot Available
References
General References
  1. Tao Y, Fishman A, Bentley WE, Wood TK: Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone. J Bacteriol. 2004 Jul;186(14):4705-13. doi: 10.1128/JB.186.14.4705-4713.2004. [PubMed:15231803  ] 
  2. SURREY AR: Pyrogallol 1-monomethyl ether. Organic Synth. 1946;26:90-2. doi: 10.1002/0471264180.os026.26. [PubMed:20280766  ] 
  3. Hirose M, Fukushima S, Hasegawa R, Kato T, Tanaka H, Ito N: Effects of sodium nitrite and catechol or 3-methoxycatechol in combination on rat stomach epithelium. Jpn J Cancer Res. 1990 Sep;81(9):857-61. doi: 10.1111/j.1349-7006.1990.tb02657.x. [PubMed:2121686  ] 
  4. Hossain MZ, Gilbert SF, Patel K, Ghosh S, Bhunia AK, Kern SE: Biological clues to potent DNA-damaging activities in food and flavoring. Food Chem Toxicol. 2013 May;55:557-67. doi: 10.1016/j.fct.2013.01.058. Epub 2013  Feb 8. [PubMed:23402862  ] 
  5. Deng H, Fang Y: The Three Catecholics Benserazide, Catechol and Pyrogallol are GPR35 Agonists. Pharmaceuticals (Basel). 2013 Apr 8;6(4):500-9. doi: 10.3390/ph6040500. [PubMed:24276120  ] 
  6. LOTUS database [Link]