Record Information
Version1.0
Creation date2010-04-08 22:13:24 UTC
Update date2019-11-26 03:15:28 UTC
Primary IDFDB017935
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameToralactone
DescriptionToralactone belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Toralactone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make toralactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Toralactone.
CAS Number41743-74-2
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.68ALOGPS
logP3.13ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.45ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.18 m³·mol⁻¹ChemAxon
Polarizability27.48 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H12O5
IUPAC name9,10-dihydroxy-7-methoxy-3-methyl-1H-benzo[g]isochromen-1-one
InChI IdentifierInChI=1S/C15H12O5/c1-7-3-8-4-9-5-10(19-2)6-11(16)12(9)14(17)13(8)15(18)20-7/h3-6,16-17H,1-2H3
InChI KeyWEHXAEGTVPWKDY-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
Classification
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • Isocoumarin
  • 1-naphthol
  • Benzopyran
  • Naphthalene
  • 2-benzopyran
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Lactone
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSToralactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abc-0190000000-0b6644937e0069cfba34Spectrum
Predicted GC-MSToralactone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uk9-2009400000-28388824cb8fdaf3e748Spectrum
Predicted GC-MSToralactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-af0e4aa15b772877e7052016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-67a31feccf2de0c2d09c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0890000000-b766d9ba09c1aa5c07ac2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-a304bd0b8e43139378852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-b199e2cdf9b618446ccb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-1980000000-284d4a71b00b8c9cc8c52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-031a5312b116bdf1aa4a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-e8cad39c3f9c861b9b612021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi9-0490000000-d32339d75f0f0ea867802021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-d6b6f6391b4e9f4522f42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-d6b6f6391b4e9f4522f42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-3970000000-0694d792101fade0dd102021-09-24View Spectrum
NMRNot Available
ChemSpider ID4479581
ChEMBL IDNot Available
KEGG Compound IDC17673
Pubchem Compound ID5321980
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38549
CRC / DFC (Dictionary of Food Compounds) IDLCB72-E:LCB72-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00032364
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
Arabica coffeeExpected but not quantifiedNot AvailableDFC CODES
Robusta coffeeExpected but not quantifiedNot AvailableDFC CODES
Showing 1 to 2 of 2 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference