Showing Compound Card for 5-ethenylbenzene-1,2,3-triol (CDB006106)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-27 17:30:09 UTC
Updated at2021-01-06 19:07:03 UTC
CannabisDB IDCDB006106
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name5-ethenylbenzene-1,2,3-triol
Description5-Ethenylbenzene-1,2,3-triol belongs to the class of organic compounds known as pyrogallols and derivatives. Pyrogallols and derivatives are compounds containing a 1,2,3-trihydroxybenzene moiety. 5-Ethenylbenzene-1,2,3-triol is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ). 5-Ethenylbenzene-1,2,3-triol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(3,4,5-trihydroxyphenyl)prop-2-enoic acid. It is generated by Hydroxycinnamate-decarboxylase enzyme via a hydroxycinnamic-acid-decarboxylation reaction. This hydroxycinnamic-acid-decarboxylation occurs in human gut microbiota.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC8H8O3
Average Molecular Weight152.15
Monoisotopic Molecular Weight152.0473
IUPAC Name5-ethenylbenzene-1,2,3-triol
Traditional Name5-ethenylbenzene-1,2,3-triol
CAS Registry NumberNot Available
SMILES
OC1=CC(C=C)=CC(O)=C1O
InChI Identifier
InChI=1S/C8H8O3/c1-2-5-3-6(9)8(11)7(10)4-5/h2-4,9-11H,1H2
InChI KeyZZMFDMIBZYLXQE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrogallols and derivatives. Pyrogallols and derivatives are compounds containing a 1,2,3-trihydroxybenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct ParentPyrogallols and derivatives
Alternative Parents
Substituents
  • Pyrogallol derivative
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

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
logP1.16ALOGPS
logP1.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)8.95ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.69 m³·mol⁻¹ChemAxon
Polarizability14.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-ethenylbenzene-1,2,3-triol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uxr-5296000000-07308ad7abc17c4bf259Spectrum
Predicted GC-MS5-ethenylbenzene-1,2,3-triol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-2900000000-88a4177c6d2e530c59daSpectrum
Predicted GC-MS5-ethenylbenzene-1,2,3-triol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS5-ethenylbenzene-1,2,3-triol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-aeb03b4e277ccaa135972019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-5885d0ef1db7b3e5b85a2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9100000000-4e597e394f0e95e66e9f2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-8e637eb26077dee4efbf2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-6a1fa55aa5073b9503e42019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9500000000-4cccd87ea1df5966596d2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-1750905022a298264c012021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-39f151a02a4660c39d352021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udm-9000000000-06c78d4f82d1805df2972021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-48f307d3f04da22f70872021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fvj-9700000000-5f3160346bfe86c4957b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-e4ac5d9b70861e1748602021-09-22View 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 IDHMDB0125528
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB084407
KNApSAcK IDNot Available
Chemspider ID11265650
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22247518
PDB IDNot Available
ChEBI IDNot Available
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