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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:31 UTC
Update Date2019-01-11 19:38:06 UTC
HMDB IDHMDB0029457
Secondary Accession Numbers
  • HMDB29457
Metabolite Identification
Common NameXanthotoxol
DescriptionXanthotoxol is found in fats and oils. Xanthotoxol is isolated from Aegle marmelos (bael fruit), Angelica archangelica (angelica) and the seeds of Pastinaca sativa (parsnip
Structure
Data?1547235486
Synonyms
ValueSource
8-HydroxyfuranocoumarinChEBI
8-HydroxypsoralenChEBI
Chemical FormulaC11H6O4
Average Molecular Weight202.165
Monoisotopic Molecular Weight202.026608673
IUPAC Name9-hydroxy-7H-furo[3,2-g]chromen-7-one
Traditional Namexanthotoxol
CAS Registry Number2009-24-7
SMILES
[H]OC1=C2OC(=O)C([H])=C([H])C2=C([H])C2=C1OC([H])=C2[H]
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point251 - 252 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-0920000000-f2a166594cf283c47f5cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-4090000000-dca534ef96e39d848c13JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-c09589cc1f633fd56111JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0190000000-3ab98291b26fe8eeb4e8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-2930000000-4691abe312d6e6ecb939JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-c887179a30886be5e421JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-4c461f4a9306d3586bfdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-0900000000-b332ff7a37ce35057295JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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
FoodDB IDNot Available
KNApSAcK IDC00000582
Chemspider IDNot Available
KEGG Compound IDC00841
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXanthotoxol
METLIN IDNot Available
PubChem Compound65090
PDB IDNot Available
ChEBI ID15709
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Xanthotoxol → 3,4,5-trihydroxy-6-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)oxane-2-carboxylic aciddetails