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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:19 UTC
Update Date2021-10-13 06:36:51 UTC
HMDB IDHMDB0033931
Secondary Accession Numbers
  • HMDB33931
Metabolite Identification
Common NameXanthoxyletin
DescriptionXanthoxyletin 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. Xanthoxyletin is found, on average, in the highest concentration within sweet oranges (Citrus sinensis). Xanthoxyletin has also been detected, but not quantified in, a few different foods, such as herbs and spices, lemons (Citrus limon), and mandarin orange (clementine, tangerine). This could make xanthoxyletin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xanthoxyletin.
Structure
Data?1563862483
Synonyms
ValueSource
5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one,9ciHMDB
5-Methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-oneHMDB
Xanthoxylin NHMDB
XanthoxyloinHMDB
XanthoxyletinMeSH
Chemical FormulaC15H14O4
Average Molecular Weight258.2693
Monoisotopic Molecular Weight258.089208936
IUPAC Name5-methoxy-8,8-dimethyl-2H,8H-pyrano[3,2-g]chromen-2-one
Traditional Namexanthoxyletin
CAS Registry Number84-99-1
SMILES
COC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O2
InChI Identifier
InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11-9(14(10)17-3)4-5-13(16)18-11/h4-8H,1-3H3
InChI KeyJSJIIHRNDMLJGK-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling Point438.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility40 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP3.640 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP10(3.05) g/LALOGPS
logP10(2.53) g/LChemAxon
logS10(-4.1) g/LALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.41 m³·mol⁻¹ChemAxon
Polarizability26.9 ųChemAxon
Number of Rings3ChemAxon
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]+160.60931661259
DarkChem[M-H]-161.96231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthoxyletinCOC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O23028.6Standard polar33892256
XanthoxyletinCOC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O22241.4Standard non polar33892256
XanthoxyletinCOC1=C2C=CC(=O)OC2=CC2=C1C=CC(C)(C)O22226.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanthoxyletin GC-MS (Non-derivatized) - 70eV, Positivesplash10-07ef-1190000000-78b72a1e70ea0b853ccc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthoxyletin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthoxyletin LC-ESI-qTof , Positive-QTOFsplash10-0uei-0940000000-f1e9eeeb83d8740504fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthoxyletin , positive-QTOFsplash10-004i-0890000000-3a18d9c240e9f36263552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Xanthoxyletin , positive-QTOFsplash10-056r-0290000000-1de65956796614ac099e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Positive-QTOFsplash10-0a4i-0090000000-aa6d574f073513b5a8292016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Positive-QTOFsplash10-0a4i-0090000000-6c6860209ee19099b43c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Positive-QTOFsplash10-0gi0-4890000000-1ab1343a5be832f0b76e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Negative-QTOFsplash10-0a4i-0090000000-573b07a2c6c0cb5cbcd52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Negative-QTOFsplash10-0a4i-0090000000-fb78f7d59b6f706256822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Negative-QTOFsplash10-01ow-0980000000-b3f729731c4334112db92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Positive-QTOFsplash10-0a4i-0090000000-5899da0eda98839d58ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Positive-QTOFsplash10-0a4i-0090000000-2cf3ccdcea338c77fa5a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Positive-QTOFsplash10-0aou-1290000000-6d0938937a8c48a429ed2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 10V, Negative-QTOFsplash10-0a4i-0090000000-c2a50a42dfada53572a92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 20V, Negative-QTOFsplash10-0aor-0090000000-bb952c86674434372ddd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthoxyletin 40V, Negative-QTOFsplash10-02ti-0290000000-4afb4baf58c4f7b7019a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB012133
KNApSAcK IDC00032520
Chemspider ID59919
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound66548
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1540341
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.. .