5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione (CHEM033940)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:32:39 UTC
Update Date2016-11-09 01:21:02 UTC
Accession NumberCHEM033940
Identification
Common Name5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione
ClassSmall Molecule
Description5-Hydroxy-4-methoxy-3-methyl-2,6-canthinedione is an alkaloid from the wood of Quassia amara (Surinam quassia).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Ethoxy-5-(1-propenyl)phenol, 9ciHMDB
2-Ethoxy-5-[(1E)-1-propenyl]phenolHMDB
5-PropenylguaetholHMDB
6-Ethoxy-m-anolHMDB
FEMA 2922HMDB
Hydroxy methyl anetholHMDB
IsosafroeugenolHMDB
IsosafroeugenoleHMDB
Propenyl guaetholHMDB
PropenylguaetholHMDB
PropenylguaetholeHMDB
PropenylguaetolHMDB
trans-2-Ethoxy-5-(1-propenyl)phenolHMDB
VanitropeHMDB
Chemical FormulaC16H12N2O4
Average Molecular Mass296.278 g/mol
Monoisotopic Mass296.080 g/mol
CAS Registry Number129724-30-7
IUPAC Name3-hydroxy-4-methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),8,10,12,14-hexaene-2,7-dione
Traditional Name3-hydroxy-4-methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-3,5(16),8,10,12,14-hexaene-2,7-dione
SMILESCOC1=C(O)C(=O)N2C3=CC=CC=C3C3=CC(=O)N(C)C1=C23
InChI IdentifierInChI=1S/C16H12N2O4/c1-17-11(19)7-9-8-5-3-4-6-10(8)18-12(9)13(17)15(22-2)14(20)16(18)21/h3-7,20H,1-2H3
InChI KeyCQFOPDQAOBCODL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.g. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassIndolonaphthyridine alkaloids
Sub ClassNot Available
Direct ParentIndolonaphthyridine alkaloids
Alternative Parents
Substituents
  • Indolo[3,2-1de][1,5]naphthyridine
  • Pyridoindolone
  • Beta-carboline
  • Pyridoindole
  • Diazanaphthalene
  • Naphthyridine
  • Indole
  • Indole or derivatives
  • Indolizine
  • Pyrrolopyridine
  • Alkyl aryl ether
  • Hydroxypyridine
  • Pyridinone
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous ester
  • Pyrrole
  • Lactam
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.27 g/LALOGPS
logP1.05ALOGPS
logP0.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)5.69ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.08 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity82.44 m³·mol⁻¹ChemAxon
Polarizability29.76 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014j-0090000000-f18fcc70ae2cd3888af2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uka-2139000000-47259223f378ce840a1aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-03d0a78eadc85e3d2ec2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0090000000-e496b4287fadced66a79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0940000000-77d22c5f183d7770885eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-b62122769f7eda50543eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-a9992798466a69d73901Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dr-1590000000-3c1312713ef14deab011Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-8c0a37cb17704175d425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-8c0a37cb17704175d425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1290000000-1772faac4465b5d9c0e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-5c316f709f7b20344764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-5c316f709f7b20344764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0950000000-4a637b057ae6fdd47a1fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0040798
FooDB IDFDB020614
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30777512
ChEBI ID174129
PubChem Compound ID5354280
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.