Showing Compound Card for p-Vinylphenol (CDB005790)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-27 16:56:51 UTC
Updated at2021-01-04 18:49:21 UTC
CannabisDB IDCDB005790
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namep-Vinylphenol
Descriptionp-Vinylphenol or 4-Vinylphenol also known as 4-Hydroxystyrene is a vinyl derivative of phenol. It belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. 4-Hydroxystyrene is one of three structural isomers of vinylphenol wherein the vinyl group is substituted at three positions of phenol (the ortho, meta and para positions). p-Vinylphenol exists as a white to pale yellow solid. It is moderately water soluble and has is a sweet, vanilla, phenolic or musty odor and a spicy, medicinal taste. In the cosmetic industry it is used as a perfuming agent. p-Vinylphenol is found in many different plant foods and beverages, such as cooked apples, coffee, cognac, coriander, corn, beer, mangos, mushrooms, peanuts, popcorn, tacos, highbush blueberries, tortilla chips, bilberries, asparagus, cauliflowers, evergreen blackberries, raspberries, sherry, strawberries, tea, and wine. In wine, p-Vinylphenol is produced by the spoilage yeast Brettanomyces. When p-Vinylphenol reaches concentrations greater than the sensory threshold, it can give the wine a barnyard, medicinal, or mousy odor. In white wines p-Vinylphenol can be found in concentrations approaching 150 μg/L. p-Vinylphenol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-VinylphenolChEBI
p-HydroxystyreneChEBI
p-VinylphenolChEBI
Chemical FormulaC8H8O
Average Molecular Weight120.15
Monoisotopic Molecular Weight120.0575
IUPAC Name4-ethenylphenol
Traditional Name4-vinylphenol
CAS Registry Number2628-17-3
SMILES
OC1=CC=C(C=C)C=C1
InChI Identifier
InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2
InChI KeyFUGYGGDSWSUORM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassStyrenes
Direct ParentStyrenes
Alternative Parents
Substituents
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point73.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.07ALOGPS
logP2.41ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.73 m³·mol⁻¹ChemAxon
Polarizability13.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSp-Vinylphenol, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-78e97f8689a1bddce8d1Spectrum
GC-MSp-Vinylphenol, non-derivatized, GC-MS Spectrumsplash10-004l-1900000000-aabb90db206495e1949cSpectrum
GC-MSp-Vinylphenol, non-derivatized, GC-MS Spectrumsplash10-0006-0900000000-78e97f8689a1bddce8d1Spectrum
GC-MSp-Vinylphenol, non-derivatized, GC-MS Spectrumsplash10-004l-1900000000-aabb90db206495e1949cSpectrum
Predicted GC-MSp-Vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6900000000-e4b2ae72210dba8376c5Spectrum
Predicted GC-MSp-Vinylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-8900000000-96525d05990bd44a73e6Spectrum
Predicted GC-MSp-Vinylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-0900000000-4748791daa3cc6db33cb2020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-b529604eb0086ce7d85a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-cc4e2accb5dbfca1223a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9300000000-1a680f497983265f70002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-992515c0effcfff517392016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-adf06e57ffef41aa20d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9600000000-7855fd6420cc0a980f562016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-2c381eb3871f5dbd6a942021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-9800000000-e2093cd31e1a5d12f8252021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9000000000-dd7dfadb6034e83a56c02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-972f865a96261dcb891a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-cc2986e6d45482e40a362021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i2d-9000000000-6a5b5c88ab894e1f72332021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0004072
DrugBank IDNot Available
Phenol Explorer Compound ID706
FoodDB IDFDB010540
KNApSAcK IDNot Available
Chemspider ID56234
KEGG Compound IDC05627
BioCyc IDCPD-1075
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7012
PubChem Compound62453
PDB IDNot Available
ChEBI ID1883
References
General ReferencesNot Available

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
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