Record Information
Version1.0
Creation date2010-04-08 22:12:03 UTC
Update date2019-11-26 03:12:12 UTC
Primary IDFDB015788
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsocolumbin
DescriptionIsocolumbin belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Isocolumbin is an extremely weak basic (essentially neutral) compound (based on its pKa). Isocolumbin is a bitter tasting compound. Isocolumbin has been detected, but not quantified in, fruits. This could make isocolumbin a potential biomarker for the consumption of these foods.
CAS Number471-54-5
Structure
Thumb
Synonyms
SynonymSource
ColumbinHMDB
4-Hydroxy-15,16-epoxycleroda-2,13(16),14-trieno-17,12-18,1-biscarbolactoneHMDB
Isocolumbindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.094 g/LALOGPS
logP2.04ALOGPS
logP2.15ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area85.97 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity90.22 m³·mol⁻¹ChemAxon
Polarizability35.96 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H22O6
IUPAC name5-(furan-3-yl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione
InChI IdentifierInChI=1S/C20H22O6/c1-18-9-14(11-5-8-24-10-11)25-16(21)12(18)3-6-19(2)15(18)13-4-7-20(19,23)17(22)26-13/h4-5,7-8,10,12-15,23H,3,6,9H2,1-2H3
InChI KeyAALLCALQGXXWNA-UHFFFAOYSA-N
Isomeric SMILESCC12CC(OC(=O)C1CCC1(C)C2C2OC(=O)C1(O)C=C2)C1=COC=C1
Average Molecular Weight358.3851
Monoisotopic Molecular Weight358.141638436
Classification
Description belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative Parents
Substituents
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Dihydropyranone
  • Delta_valerolactone
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.03%; H 6.19%; O 26.79%DFC
Melting PointMp 190°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 210 (log e 3.73) (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9343000000-203979a397d79b38254cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9345300000-3e0f182125c118daf9c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-ed8a8344267df5885043JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-2339000000-0787a711e926bbba1f0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-4920000000-3a8b9ed779ff72e90068JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-41ee4679957e2aa1a2efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-1019000000-b414a9be9ca19b5cedc3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-3093000000-0c9a6635438ebbc131e9JSpectraViewer
ChemSpider ID196539
ChEMBL IDNot Available
KEGG Compound IDC17508
Pubchem Compound ID226036
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36837
CRC / DFC (Dictionary of Food Compounds) IDJGJ04-F:KJB79-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference