Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2018-05-28 22:35:44 UTC
Primary IDFDB000578
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthotoxol
DescriptionIsolated from Aegle marmelos (bael fruit), Angelica archangelica (angelica) and the seeds of Pastinaca sativa (parsnip). Xanthotoxol is found in many foods, some of which are fats and oils, green vegetables, herbs and spices, and fig.
CAS Number2009-24-7
Structure
Thumb
Synonyms
SynonymSource
8-HydroxyfuranocoumarinChEBI
8-HydroxypsoralenChEBI
5-Benzofuranacrylic acid, 6,7-dihydroxy-, gamma-lactonebiospider
6,7-Dihydroxy-5-benzofuranacrylic acid gamma-lactonebiospider
7H-Furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy-biospider
7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-biospider
8-Hydroxy-psoralenHMDB
8-Hydroxyanthotoxolbiospider
8-hydroxyfuranocoumarinsbiospider
8-hydroxyfurocoumarinbiospider
8-hydroxyfurocoumarinsbiospider
8-Hydroxypsoralenebiospider
9-Hydroxy-7H-furo(3,2-g)(1)benzopyran-7-onebiospider
9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-oneHMDB
9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CIdb_source
9-hydroxy-7H-furo[3,2-g]chromen-7-onebiospider
an 8-hydroxyfurocoumarinbiospider
Psoralen, 8-hydroxy-biospider
Xanthotoxol (6CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP1.9ALOGPS
logP2.29ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.19ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.67 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.37 m³·mol⁻¹ChemAxon
Polarizability19.01 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H6O4
IUPAC name9-hydroxy-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H
InChI KeyJWVYQQGERKEAHW-UHFFFAOYSA-N
Isomeric SMILES[H]OC1=C2OC(=O)C([H])=C([H])C2=C([H])C2=C1OC([H])=C2[H]
Average Molecular Weight202.165
Monoisotopic Molecular Weight202.026608673
Classification
Description belongs to the class of organic compounds known as 8-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C8 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent8-hydroxypsoralens
Alternative Parents
Substituents
  • 8-hydroxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.35%; H 2.99%; O 31.66%DFC
Melting PointMp 251-252°DFC
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0920000000-f2a166594cf283c47f5cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-4090000000-dca534ef96e39d848c13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-c09589cc1f633fd56111View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0190000000-3ab98291b26fe8eeb4e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-2930000000-4691abe312d6e6ecb939View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-c887179a30886be5e421View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-4c461f4a9306d3586bfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-0900000000-b332ff7a37ce35057295View in MoNA
ChemSpider ID58600
ChEMBL IDCHEMBL1192
KEGG Compound IDC00841
Pubchem Compound ID65090
Pubchem Substance IDNot Available
ChEBI ID15709
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29457
CRC / DFC (Dictionary of Food Compounds) IDBDW00-J:BDW00-J
EAFUS IDNot Available
Dr. Duke IDXANTHOTOXOL
BIGG IDNot Available
KNApSAcK IDC00000582
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
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti mitoticDUKE
anti nicotinic38323 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.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.