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Xanthotoxin (FDB012474)

Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2019-11-26 03:06:52 UTC
Primary IDFDB012474
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthotoxin
DescriptionPresent in celery, especies the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. Isolated from Aegle marmelos (bael) Methoxsalen (marketed under the trade name Oxsoralen) is a drug used to treat psoriasis, eczema, vitiligo, and some cutaneous Lymphomas in conjunction with exposing the skin to sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. The dosage comes in 10mg tablets, which are taken in the amount of 30mg 75 minutes before a PUVA light treatment. The substance is also present in bergamot oil which is used in many perfumes and aromatherapy oils.; Methoxsalen selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Methoxsalen-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.; Patients with high blood pressure or a history of liver problems are at risk for inflammation and irreparable damage to both liver and skin. The eyes must be protected from UVA radiation. Side effects include nausea, headaches, dizziness, and in rare cases insomnia. When Eau de Cologne was made, it became a popular perfume. It contained bergamot oil as one of its components. Ladies wearing the perfume on places where the skin was radiated by the sun, noticed that their skin turned brownish at those spots. This is due to the phototoxic effects of methoxsalen present in the bergamot oil. The methoxsalen was removed, and most modern formulations of perfumes containing bergamot are de-methoxsalenised. Xanthotoxin is found in many foods, some of which are parsley, wild celery, dill, and angelica.
CAS Number298-81-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.1ALOGPS
logP1.78ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.85 m³·mol⁻¹ChemAxon
Polarizability20.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H8O4
IUPAC name9-methoxy-7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChI KeyQXKHYNVANLEOEG-UHFFFAOYSA-N
Isomeric SMILESCOC1=C2OC(=O)C=CC2=CC2=C1OC=C2
Average Molecular Weight216.192
Monoisotopic Molecular Weight216.042258738
Classification
Description Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent8-methoxypsoralens
Alternative Parents
Substituents
  • 8-methoxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-9670000000-3e0fa2e9c81c3bc1d9362014-09-20View Spectrum
GC-MSXanthotoxin, non-derivatized, GC-MS Spectrumsplash10-00ri-6940000000-921a3e8adbbde5f7a0c3Spectrum
GC-MSXanthotoxin, non-derivatized, GC-MS Spectrumsplash10-003b-4950000000-4e2c001531825f6dddcaSpectrum
GC-MSXanthotoxin, non-derivatized, GC-MS Spectrumsplash10-00ri-6940000000-921a3e8adbbde5f7a0c3Spectrum
GC-MSXanthotoxin, non-derivatized, GC-MS Spectrumsplash10-003b-4950000000-4e2c001531825f6dddcaSpectrum
Predicted GC-MSXanthotoxin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1920000000-98f6cfda190045d0762aSpectrum
Predicted GC-MSXanthotoxin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-1590000000-f70cf2b0756e8c80c17b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0890000000-f76d6fb28854a5d7b6cd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fk9-0920000000-c2bd0b76c5aed757e9042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-cecd035cc60695427f782017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0290000000-2e17076c991ea61ced1a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uk9-0970000000-59c3b8004baa44f8d3a52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0190000000-cc04ec8c7265ba3a72972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0970000000-82c4c7eefd54ad509f692017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00xs-0900000000-991b5b7dc028219e593b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0970000000-dc6cd01d5d2e5eeaae302017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0970000000-ee8aa480dca6e72a74fb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0890000000-f76d6fb28854a5d7b6cd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-1590000000-f70cf2b0756e8c80c17b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0fk9-0920000000-c2bd0b76c5aed757e9042017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0gi0-1960000000-82bc07f73bc5b20446422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0690000000-770dc5d0db7e86d8ba072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00dj-0900000000-b06196cd7070da3a2e982021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0090000000-ed4db851d39c50628cea2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0uxr-0490000000-6e7169196da6a70b89d62021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-4767833559e7bd183ce02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-c471bf567e8a63e00e512015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-0930000000-72a72a3eb013e045bdb02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-c9557f276875a3bf1d2b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0390000000-ff927b8db6ef70ef822d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0910000000-d2e511be224be1b3530e2015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
ChemSpider ID3971
ChEMBL IDCHEMBL416
KEGG Compound IDC01864
Pubchem Compound ID4114
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID719
DrugBank IDDB00553
HMDB IDHMDB14693
CRC / DFC (Dictionary of Food Compounds) IDHHG12-C:HHG12-C
EAFUS IDNot Available
Dr. Duke ID8-METHOXY-PSORALEN|XANTHOTOXIN
BIGG IDNot Available
KNApSAcK IDC00000576
HET ID8MO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDXanthotoxin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.