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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:00:58 UTC
Update Date2022-03-07 02:55:05 UTC
HMDB IDHMDB0036837
Secondary Accession Numbers
  • HMDB36837
Metabolite Identification
Common 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. Outside of the human body, isocolumbin has been detected, but not quantified in, fruits. This could make isocolumbin a potential biomarker for the consumption of these foods.
Structure
Data?1563862935
Synonyms
ValueSource
ColumbinHMDB
4-Hydroxy-15,16-epoxycleroda-2,13(16),14-trieno-17,12-18,1-biscarbolactoneHMDB
Chemical FormulaC20H22O6
Average Molecular Weight358.3851
Monoisotopic Molecular Weight358.141638436
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
Traditional 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
CAS Registry Number471-54-5
SMILES
CC12CC(OC(=O)C1CCC1(C)C2C2OC(=O)C1(O)C=C2)C1=COC=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.60431661259
DarkChem[M-H]-179.73531661259
DeepCCS[M-2H]-220.68330932474
DeepCCS[M+Na]+196.23630932474
AllCCS[M+H]+185.432859911
AllCCS[M+H-H2O]+182.432859911
AllCCS[M+NH4]+188.132859911
AllCCS[M+Na]+188.832859911
AllCCS[M-H]-189.632859911
AllCCS[M+Na-2H]-189.432859911
AllCCS[M+HCOO]-189.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsocolumbinCC12CC(OC(=O)C1CCC1(C)C2C2OC(=O)C1(O)C=C2)C1=COC=C13722.7Standard polar33892256
IsocolumbinCC12CC(OC(=O)C1CCC1(C)C2C2OC(=O)C1(O)C=C2)C1=COC=C12548.2Standard non polar33892256
IsocolumbinCC12CC(OC(=O)C1CCC1(C)C2C2OC(=O)C1(O)C=C2)C1=COC=C13278.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isocolumbin,1TMS,isomer #1CC12CC(C3=COC=C3)OC(=O)C1CCC1(C)C2C2C=CC1(O[Si](C)(C)C)C(=O)O23043.9Semi standard non polar33892256
Isocolumbin,1TBDMS,isomer #1CC12CC(C3=COC=C3)OC(=O)C1CCC1(C)C2C2C=CC1(O[Si](C)(C)C(C)(C)C)C(=O)O23300.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isocolumbin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9343000000-203979a397d79b38254c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocolumbin GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9345300000-3e0f182125c118daf9c22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocolumbin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocolumbin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocolumbin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 10V, Positive-QTOFsplash10-0a4i-0009000000-ed8a8344267df58850432015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 20V, Positive-QTOFsplash10-052f-2339000000-0787a711e926bbba1f0a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 40V, Positive-QTOFsplash10-0gbi-4920000000-3a8b9ed779ff72e900682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 10V, Negative-QTOFsplash10-0a4i-0009000000-41ee4679957e2aa1a2ef2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 20V, Negative-QTOFsplash10-0bt9-1019000000-b414a9be9ca19b5cedc32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 40V, Negative-QTOFsplash10-00lr-3093000000-0c9a6635438ebbc131e92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 10V, Positive-QTOFsplash10-0a4i-0019000000-a2ebfe0bbc9fb42733ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 20V, Positive-QTOFsplash10-0a4i-1079000000-b0d8d2117734853e22d22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 40V, Positive-QTOFsplash10-0a4i-4249000000-7a45b52506d479da515d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 10V, Negative-QTOFsplash10-0a4i-0009000000-43b8456c3212fa27f7412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 20V, Negative-QTOFsplash10-0a4i-2009000000-921df96e091caa9a5fc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocolumbin 40V, Negative-QTOFsplash10-00rm-9085000000-5cb516886c572b1c7db32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 IDFDB015788
KNApSAcK IDNot Available
Chemspider ID196539
KEGG Compound IDC17508
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound226036
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .