Back to Compounds

Showing Compound Xanthyletin (FDB004984)

Record Information
Version1.0
Creation date2010-04-08 22:06:29 UTC
Update date2019-11-26 03:00:19 UTC
Primary IDFDB004984
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthyletin
DescriptionXanthyletin is a member of the class of compounds known as linear pyranocoumarins. Linear pyranocoumarins are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Xanthyletin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthyletin can be found in lemon, lime, mandarin orange (clementine, tangerine), and sweet orange, which makes xanthyletin a potential biomarker for the consumption of these food products.
CAS Number553-19-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
XanthyletineMeSH
2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one, 8,8-dimethyl-biospider
8,8-Dimethyl-2H,8H-benzo(1,2-b:5,4-b')dipyran-2-onebiospider
8,8-Dimethyl-2H,8H-pyrano[3,2-g]chromen-2-onebiospider
Xanthyletinbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.037 g/LALOGPS
logP3.05ALOGPS
logP2.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.94 m³·mol⁻¹ChemAxon
Polarizability24.11 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H12O3
IUPAC name8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one
InChI IdentifierInChI=1S/C14H12O3/c1-14(2)6-5-10-7-9-3-4-13(15)16-11(9)8-12(10)17-14/h3-8H,1-2H3
InChI KeyQOTBQNVNUBKJMS-UHFFFAOYSA-N
Isomeric SMILESCC1(C)OC2=C(C=C1)C=C1C=CC(=O)OC1=C2
Average Molecular Weight228.2433
Monoisotopic Molecular Weight228.07864425
Classification
Description Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentLinear pyranocoumarins
Alternative Parents
Substituents
  • Linear pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-6836eeb226b2d716b6d92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1490000000-da8982de5fe1e4f2ccff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g4u-2900000000-54bf7ac4db78ac13bfae2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-d010a8f19a97b19674142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0290000000-3580a581a6d0645f31752016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0900-0920000000-eda96f0f1aebfc8818b52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-c89325e1a7192ec227f42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0590000000-d99982551340bd6552e42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-1930000000-3102368b1d2f4dfc1db42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f0e0fc28215258fdeb312021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-9ead24104d27d113c8732021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-0910000000-3c052f1765e977ee98862021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09317
Pubchem Compound ID65188
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDXANTHYLETIN
BIGG IDNot Available
KNApSAcK IDC00002505
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 / Bioactivities
DescriptorIDDefinitionReference
diabetic-macular-edema inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.