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Showing Compound Xanthotoxol (FDB000578)

Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2025-11-18 22:20:01 UTC
Primary IDFDB000578
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthotoxol
DescriptionXanthotoxol, also known as 8-hydroxypsoralen, 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. Xanthotoxol exists in all living organisms, ranging from bacteria to humans. Xanthotoxol has been detected, but not quantified in, several different foods, such as figs (Ficus carica), parsleys (Petroselinum crispum), herbs and spices, green vegetables, and fats and oils. This could make xanthotoxol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Xanthotoxol.
CAS Number2009-24-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthotoxol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-0920000000-f2a166594cf283c47f5cSpectrum
Predicted GC-MSXanthotoxol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00e9-4090000000-dca534ef96e39d848c13Spectrum
Predicted GC-MSXanthotoxol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-c09589cc1f633fd561112016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0190000000-3ab98291b26fe8eeb4e82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-2930000000-4691abe312d6e6ecb9392016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-c887179a30886be5e4212016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-4c461f4a9306d3586bfd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-0900000000-b332ff7a37ce350572952016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-2e5a86e101fa40f235c92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0290000000-f0e15e059d45f78f5b762021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-0900000000-5f24b0525848ab6177532021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6f70ceb2368baddf4f402021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-6f70ceb2368baddf4f402021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-1553b0f99d6356baaebd2021-09-25View Spectrum
NMRNot Available
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 IDXanthotoxol
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 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti mitoticAn agent that inhibits mitosis, or cell division, playing a crucial role in regulating cell growth. Therapeutically, it is used to treat cancer by blocking tumor cell proliferation. Key medical uses include chemotherapy for various cancers, such as breast, lung, and colon cancer, to prevent cancer cell division and growth.DUKE
Anti nicotinic38323 An agent that blocks nicotinic acetylcholine receptors, reducing neurotransmitter activity. Therapeutically, it's used to treat conditions like myasthenia gravis, muscle spasms, and certain types of poisoning, as well as to provide neuromuscular blockade during surgery.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.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.