Showing metabocard for Guaiacol (MMDBc0053306)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-05-16 21:20:22 UTC
Update Date2024-09-28 00:38:52 UTC
Metabolite IDMMDBc0053306
Metabolite Identification
Common NameGuaiacol
DescriptionGuaiacol is a phenolic compound with a methoxy group and is the monomethyl ether of catechol. Guaiacol is readily oxidized by the heme iron of peroxidases including the peroxidase of cyclooxygenase (COX) enzymes. It therefore serves as a reducing co-substrate for COX reactions. Guaiacol is a phenolic natural product first isolated from Guaiac resin and the oxidation of lignin. It is a yellowish aromatic oil that is now commonly derived from guaiacum or wood creosote. It is used medicinally as an expectorant, antiseptic, and local anesthetic. Guaiacol is used in traditional dental pulp sedation, and has the property of inducing cell proliferation; guaiacol is a potent scavenger of reactive oxygen radicals and its radical scavenging activity may be associated with its effect on cell proliferation. Guaiacol is also used in the preparation of synthetic vanillin. Guaiacol is also present in wood smoke, as a product of pyrolysis of lignin. Guaiacol has been found in the urine of patients with neuroblastoma and pheochromocytoma. (PMID 4344880 , 16152729 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f920706a1a8>


  Mrv1652309272007312D          

  9  9  0  0  0  0            999 V2000
    6.7181   -6.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -5.3890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -6.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -7.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4476   -6.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f920706a1a8>

HMDB0001398
     RDKit          3D
Guaiacol
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.3932    0.9830   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638   -0.1930   -0.0709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3784   -0.1498    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.9388   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678    0.9600   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817   -0.1835    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6698   -1.3102    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.2781    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -2.3974    0.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    1.7597    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403    1.3398   -1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4584    0.7099   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    1.8265   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255    1.8596   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4644   -0.2152    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388   -2.2136    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4415   -2.4365    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f920706a1a8>


  Mrv1652309272007312D          

  9  9  0  0  0  0            999 V2000
    6.7181   -6.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -5.3890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -6.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0095   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -6.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008   -7.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4476   -6.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  2  4  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053306

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C=CC=C1

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

> <INCHI_KEY>
LHGVFZTZFXWLCP-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.139

> <EXACT_MASS>
124.052429498

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.686283084612246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxyphenol

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
1.5120092286666669

> <ALOGPS_LOGS>
-0.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.977540753803286

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8904950754181264

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
34.5021

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.74e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guaiacol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x00007f920706a1a8>

HMDB0001398
     RDKit          3D
Guaiacol
 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.3932    0.9830   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7638   -0.1930   -0.0709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3784   -0.1498    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.9388   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678    0.9600   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817   -0.1835    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6698   -1.3102    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976   -1.2781    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -2.3974    0.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    1.7597    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9403    1.3398   -1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4584    0.7099   -0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1231    1.8265   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255    1.8596   -0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4644   -0.2152    0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1388   -2.2136    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4415   -2.4365    0.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
M  END
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PDB for #<Metabolite:0x00007f920706a1a8>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0      12.540 -11.618   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.895 -10.059   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.218 -12.398   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.895 -11.618   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.218 -13.956   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.567 -12.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.895 -14.736   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.567 -13.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.902 -12.406   0.000  0.00  0.00           C+0
CONECT    1    3    9                                                       
CONECT    2    4                                                            
CONECT    3    1    4    5                                                  
CONECT    4    2    3    6                                                  
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x00007f920706a1a8>

COMPND    HMDB0001398
HETATM    1  C1  UNL     1      -2.393   0.983  -0.547  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.764  -0.193  -0.071  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.378  -0.150   0.026  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.381   0.939  -0.306  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.768   0.960  -0.201  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.382  -0.183   0.262  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.670  -1.310   0.611  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.298  -1.278   0.488  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.445  -2.397   0.832  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.483   1.760   0.238  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.940   1.340  -1.480  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.458   0.710  -0.809  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.123   1.826  -0.667  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.326   1.860  -0.480  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.464  -0.215   0.361  1.00  0.00           H  
HETATM   16  H7  UNL     1       2.139  -2.214   0.975  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.442  -2.437   0.765  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   13
CONECT    5    6    6   14
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9
CONECT    9   17
END
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SMILES for #<Metabolite:0x00007f920706a1a8>

COC1=C(O)C=CC=C1
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INCHI for #<Metabolite:0x00007f920706a1a8>

InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
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Synonyms
ValueSource
1-Hydroxy-2-methoxybenzeneChEBI
2-HydroxyanisoleChEBI
Catechol monomethyl etherChEBI
O-MethoxyphenolChEBI
CreodonKegg
2-MethoxyphenolHMDB
2-Methoxy-phenolHMDB
AnastilHMDB
Guaiacol (liquid) extra pureHMDB
GuaiastilHMDB
GuaicolHMDB
GuaicolinaHMDB
GuajakolHMDB
GuajolHMDB
GuasolHMDB
GuiacolHMDB
MethoxyphenolHMDB
MethylcatacholHMDB
MethylcatecholHMDB
O-GuaiacolHMDB
O-HydroxyanisoleHMDB
O-Methoxy-phenolHMDB
O-Methyl catecholHMDB
Pyrocatechol monomethyl etherHMDB
Pyroguaiac acidHMDB
2-Hydroxy-anisoleHMDB
Catechol, methylHMDB
Methyl catecholHMDB
2-Methoxyl-4-vinylphenolHMDB
GuaiacolHMDB
Molecular FormulaC7H8O2
Average Mass124.139
Monoisotopic Mass124.052429498
IUPAC Name2-methoxyphenol
Traditional Nameguaiacol
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC=C1
InChI Identifier
InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
InChI KeyLHGVFZTZFXWLCP-UHFFFAOYSA-N