Hmdb loader

Showing metabocard for 2-Methoxy-4-vinylphenol (HMDB0013744)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:48 UTC
Update Date2023-02-21 17:18:02 UTC
HMDB IDHMDB0013744
Secondary Accession Numbers
  • HMDB13744
Metabolite Identification
Common Name2-Methoxy-4-vinylphenol
Description2-Methoxy-4-vinylphenol, also known as 4-hydroxy-3-methoxystyrene or 4-vinylguaiacol, 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. 2-Methoxy-4-vinylphenol exists in all eukaryotes, ranging from yeast to plants to humans. 2-Methoxy-4-vinylphenol is a clove, curry, and peanut tasting compound. 2-Methoxy-4-vinylphenol is found, on average, in the highest concentration within a few different foods, such as wild carrots (Daucus carota), carrots (Daucus carota ssp. sativus), and red wine and in a lower concentration in arabica coffees (Coffea arabica), kohlrabis (Brassica oleracea var. gongylodes), and beer. 2-Methoxy-4-vinylphenol has also been detected, but not quantified in, several different foods, such as oats (Avena sativa), tortilla, asparagus (Asparagus officinalis), spearmints (Mentha spicata), and tortilla chip. This could make 2-methoxy-4-vinylphenol a potential biomarker for the consumption of these foods. 2-Methoxy-4-vinylphenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2-Methoxy-4-vinylphenol.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013744 (2-Methoxy-4-vinylphenol)

  Mrv1652304272018572D          

 11 11  0  0  0  0            999 V2000
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    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  3  2  0  0  0  0
  2 11  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0013744 (2-Methoxy-4-vinylphenol)

HMDB0013744
     RDKit          3D
2-Methoxy-4-vinylphenol
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.4621   -0.8290    0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327   -1.2023   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -0.2402    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239    1.0515    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768    1.9473    0.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100    1.5283    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    2.4026    0.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2324    0.2385   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -0.1235   -0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -1.4067   -0.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1772   -0.6231   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977    0.1303    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2777   -1.5589   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186   -2.2039   -0.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    1.4087    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465    2.9595    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    3.3492    0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579   -1.8503   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963   -2.0510    0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.2992   -1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353   -1.6278   -0.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
 10 18  1  0
 10 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for HMDB0013744 (2-Methoxy-4-vinylphenol)

  Mrv1652304272018572D          

 11 11  0  0  0  0            999 V2000
    1.6500    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    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  3  2  0  0  0  0
  2 11  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013744

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3

> <INCHI_KEY>
YOMSJEATGXXYPX-UHFFFAOYSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.98631844617077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-ethenyl-2-methoxyphenol

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
2.2487112966666665

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.034622277956638

> <JCHEM_PKA_STRONGEST_BASIC>
-4.89373168768089

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
44.18840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-4-vinyl-phenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0013744 (2-Methoxy-4-vinylphenol)

HMDB0013744
     RDKit          3D
2-Methoxy-4-vinylphenol
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.4621   -0.8290    0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2327   -1.2023   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1460   -0.2402    0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239    1.0515    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768    1.9473    0.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100    1.5283    0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963    2.4026    0.5320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2324    0.2385   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -0.1235   -0.3219 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -1.4067   -0.7686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1772   -0.6231   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7977    0.1303    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2777   -1.5589   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186   -2.2039   -0.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    1.4087    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465    2.9595    0.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    3.3492    0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579   -1.8503   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9963   -2.0510    0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.2992   -1.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353   -1.6278   -0.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
 10 18  1  0
 10 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

PDB for HMDB0013744 (2-Methoxy-4-vinylphenol)

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       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   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       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   11                                                            
CONECT    3    1    7                                                       
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    7    9                                                       
CONECT    7    3    4    6                                                  
CONECT    8    5    9   10                                                  
CONECT    9    6    8   11                                                  
CONECT   10    8                                                            
CONECT   11    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
Download

3D PDB for HMDB0013744 (2-Methoxy-4-vinylphenol)

COMPND    HMDB0013744
HETATM    1  C1  UNL     1      -3.462  -0.829   0.114  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.233  -1.202  -0.140  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.146  -0.240   0.047  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.324   1.052   0.478  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.277   1.947   0.648  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.010   1.528   0.373  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.096   2.403   0.532  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.232   0.239  -0.062  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.549  -0.123  -0.322  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.896  -1.407  -0.769  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.177  -0.623  -0.220  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.798   0.130   0.456  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.278  -1.559  -0.029  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.019  -2.204  -0.482  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.296   1.409   0.698  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.447   2.960   0.989  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.937   3.349   0.851  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.158  -1.850  -1.447  1.00  0.00           H  
HETATM   19  H8  UNL     1       2.996  -2.051   0.132  1.00  0.00           H  
HETATM   20  H9  UNL     1       3.891  -1.299  -1.291  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.335  -1.628  -0.557  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   14
CONECT    3    4    4   11
CONECT    4    5   15
CONECT    5    6    6   16
CONECT    6    7    8
CONECT    7   17
CONECT    8    9   11   11
CONECT    9   10
CONECT   10   18   19   20
CONECT   11   21
END
Download

SMILES for HMDB0013744 (2-Methoxy-4-vinylphenol)

COC1=C(O)C=CC(C=C)=C1
Download

INCHI for HMDB0013744 (2-Methoxy-4-vinylphenol)

InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3
Download
View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Name4-ethenyl-2-methoxyphenol
Traditional Name2-methoxy-4-vinyl-phenol
CAS Registry Number7786-61-0
SMILES
COC1=C(O)C=CC(C=C)=C1
InChI Identifier
InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3
InChI KeyYOMSJEATGXXYPX-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
  • Styrene
  • Phenol ether
  • Anisole
  • 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 locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
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 IDDB03514
Phenol Explorer Compound ID632
FooDB IDFDB000857
KNApSAcK IDC00029546
Chemspider ID325
KEGG Compound IDC17883
BioCyc IDCPD-1072
BiGG IDNot Available
Wikipedia Link2-Methoxy-4-vinylphenol
METLIN IDNot Available
PubChem Compound332
PDB IDNot Available
ChEBI ID42438
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wagenstaller M, Buettner A: Quantitative determination of common urinary odorants and their glucuronide conjugates in human urine. Metabolites. 2013 Aug 7;3(3):637-57. doi: 10.3390/metabo3030637. [PubMed:24958143 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Methoxy-4-vinylphenol → 6-(4-ethenyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Enzyme Details
2. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
2-Methoxy-4-vinylphenol → (4-ethenyl-2-methoxyphenyl)oxidanesulfonic aciddetails