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Showing metabocard for Guaiacol (HMDB0001398)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:40 UTC
HMDB IDHMDB0001398
Secondary Accession Numbers
  • HMDB01398
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
Data?1676999740
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001398 (Guaiacol)

  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 HMDB0001398 (Guaiacol)

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 HMDB0001398 (Guaiacol)

  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>
HMDB0001398

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0001398 (Guaiacol)

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 HMDB0001398 (Guaiacol)

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 HMDB0001398 (Guaiacol)

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 HMDB0001398 (Guaiacol)

COC1=C(O)C=CC=C1
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INCHI for HMDB0001398 (Guaiacol)

InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC7H8O2
Average Molecular Weight124.139
Monoisotopic Molecular Weight124.052429498
IUPAC Name2-methoxyphenol
Traditional Nameguaiacol
CAS Registry Number90-05-1
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
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
  • 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 Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.7 mg/mL at 15 °CNot Available
LogP1.32HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified8.5 +/- 1.0 uMAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Intestinal infections		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Enteritis
  1. Probert CS, Jones PR, Ratcliffe NM: A novel method for rapidly diagnosing the causes of diarrhoea. Gut. 2004 Jan;53(1):58-61. [PubMed:14684577 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDDB11359
Phenol Explorer Compound ID650
FooDB IDFDB011885
KNApSAcK IDC00029459
Chemspider ID447
KEGG Compound IDC15572
BioCyc IDCPD-400
BiGG IDNot Available
Wikipedia LinkGuaiacol
METLIN ID6217
PubChem Compound460
PDB IDNot Available
ChEBI ID28591
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChen, Jiehua; Xu, Baocai; Zhang, Hong; Ye, Jianfeng. Method for preparing guaiacol from catechol and dimethyl carbonate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 6pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tsibris JC, Virgin SD, Khan-Dawood FS, Langenberg PW, Thomason JL, Spellacy WN: Cervicovaginal peroxidases: markers of the fertile period. Obstet Gynecol. 1986 Mar;67(3):316-20. [PubMed:3003635 ]
  2. Bieniek G, Kurkiewicz S, Wilczok T, Klimek K, Swiatkowska L, Lusiak A: occupational exposure to aromatic hydrocarbons at a coke plant: Part II. Exposure assessment of volatile organic compounds. J Occup Health. 2004 May;46(3):181-6. [PubMed:15215658 ]
  3. Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. [PubMed:11334365 ]
  4. Mutlib AE, Klein JT: Application of liquid chromatography/mass spectrometry in accelerating the identification of human liver cytochrome P450 isoforms involved in the metabolism of iloperidone. J Pharmacol Exp Ther. 1998 Sep;286(3):1285-93. [PubMed:9732390 ]
  5. Rogers LE, Lyon GM Jr, Porter FS: Spot test for vanillylmandelic acid and other guaiacols in urine of patients with neuroblastoma. Am J Clin Pathol. 1972 Oct;58(4):383-7. [PubMed:4344880 ]
  6. Pruitt KM, Kamau DN, Miller K, Mansson-Rahemtulla B, Rahemtulla F: Quantitative, standardized assays for determining the concentrations of bovine lactoperoxidase, human salivary peroxidase, and human myeloperoxidase. Anal Biochem. 1990 Dec;191(2):278-86. [PubMed:1964765 ]
  7. Kupfer A, Lawson J, Branch RA: Stereoselectivity of the arene epoxide pathway of mephenytoin hydroxylation in man. Epilepsia. 1984 Feb;25(1):1-7. [PubMed:6420144 ]
  8. Mimurai T, Yazaki K, Sawaki K, Ozawa T, Kawaguchi M: Hydroxyl radical scavenging effects of guaiacol used in traditional dental pulp sedation: reaction kinetic study. Biomed Res. 2005 Aug;26(4):139-45. [PubMed:16152729 ]

Enzymes

Enzyme Details
1. Catechol O-methyltransferase
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Pyrocatechol → Guaiacoldetails
Enzyme Details
2. Transmembrane O-methyltransferase
General function:
Involved in O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones (By similarity). Required for auditory function.
Gene Name:
LRTOMT
Uniprot ID:
Q8WZ04
Molecular weight:
32154.43