You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 05:40:15 UTC
Update Date2019-11-12 17:21:42 UTC
HMDB IDHMDB0128660
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoic acid
Description3-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoic acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 3-(6,7-dimethoxy-2h-1,3-benzodioxol-5-yl)prop-2-enoic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(6,7-dimethoxy-2h-1,3-benzodioxol-5-yl)prop-2-enal. 3-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by cyp1a2 and cyp3a4 enzymes via an aldehyde-oxidation reaction. This aldehyde-oxidation occurs in humans.
Structure
Data?1563875415
Synonyms
ValueSource
3-(6,7-Dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoateGenerator
Chemical FormulaC12H12O6
Average Molecular Weight252.222
Monoisotopic Molecular Weight252.063388106
IUPAC Name3-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoic acid
Traditional Name3-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C(C=CC(O)=O)=CC2=C1OCO2
InChI Identifier
InChI=1S/C12H12O6/c1-15-10-7(3-4-9(13)14)5-8-11(12(10)16-2)18-6-17-8/h3-5H,6H2,1-2H3,(H,13,14)
InChI KeyNLWULWMJACYONC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Benzodioxole
  • Anisole
  • Styrene
  • Alkyl aryl ether
  • Benzenoid
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.76ALOGPS
logP1.44ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity61.75 m³·mol⁻¹ChemAxon
Polarizability24.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0abc-3093000000-71159a6f0beb24d1af17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-0190000000-3bd0c4bb6d2045b97631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-29eacfadccbc02478185Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbi-0190000000-67d966402cf1c92ae249Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-3920000000-a58f6c6301bd195b2d22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d54f3b3b91e3626ee4a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgi-0190000000-ad977f801388dc7b208eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00vi-3900000000-918122ee728bf569778dSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53397112
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

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
3-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoic acid → 6-{[3-(6,7-dimethoxy-2H-1,3-benzodioxol-5-yl)prop-2-enoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails