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CHEBI:18358 - methoxsalen

ChEBI IDCHEBI:18358
ChEBI Namemethoxsalen
Stars
DefinitionA member of the class of psoralens that is 7H-furo[3,2-g]chromen-7-one in which the 9 position is substituted by a methoxy group. It is a constituent of the fruits of Ammi majus. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered topically or orally in conjunction with UV-A for phototherapy treatment of vitiligo and severe psoriasis.
Secondary ChEBI IDsCHEBI:10068, CHEBI:12268, CHEBI:12715, CHEBI:21960, CHEBI:27330, CHEBI:27331, CHEBI:29040, CHEBI:40342, CHEBI:101063
Last Modified19 June 2017
DownloadsMolfile
FormulaC12H8O4
Net Charge0
Average Mass216.192
Monoisotopic Mass216.04226
SMILESCOc1c2occc2cc2ccc(=O)oc12
InChIInChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChIKeyQXKHYNVANLEOEG-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Ammi majus (ncbitaxon:48026) - PubMed (15009205)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
dermatologic drug  A drug used to treat or prevent skin disorders or for the routine care of skin.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
cross-linking reagent  A reagent with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between macromolecules, principally side chains of amino acids in proteins, allowing the locations of naturally reactive areas within the proteins to be identified.
photosensitizing agent  A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
ChEBI Ontology
Outgoing Relation(s)
methoxsalen (CHEBI:18358) has functional parent psoralen (CHEBI:27616)
methoxsalen (CHEBI:18358) has role antineoplastic agent (CHEBI:35610)
methoxsalen (CHEBI:18358) has role cross-linking reagent (CHEBI:50684)
methoxsalen (CHEBI:18358) has role dermatologic drug (CHEBI:50177)
methoxsalen (CHEBI:18358) has role photosensitizing agent (CHEBI:47868)
methoxsalen (CHEBI:18358) has role plant metabolite (CHEBI:76924)
methoxsalen (CHEBI:18358) is a aromatic ether (CHEBI:35618)
methoxsalen (CHEBI:18358) is a psoralens (CHEBI:26369)
Incoming Relation(s)
5-hydroxyxanthotoxin (CHEBI:2082) has functional parent methoxsalen (CHEBI:18358)
IUPAC Name 
9-methoxy-7H-furo[3,2-g]chromen-7-one
Synonyms  Source
XanthotoxinKEGG COMPOUND
MethoxsalenKEGG COMPOUND
8-MethoxyfuranocoumarinKEGG COMPOUND
O-methylxanthotoxolChEBI
8-methoxypsoralenChemIDplus
9-methoxy-7H-furo[3,2-g][1]benzopyran-7-oneNIST Chemistry WebBook
Brand Names  Source
MeladinineDrugBank
OxsoralenDrugBank
Ultra MopDrugBank
UvadexDrugBank
MeloxineChemIDplus
UniProt Name  Source
xanthotoxinUniProt
Manual XrefsDatabases
C01864KEGG COMPOUND
D00139KEGG DRUG
8MOPDBeChem
DB00553DrugBank
US2889337Patent
MethoxsalenWikipedia
HMDB0014693HMDB
C00000576KNApSAcK
LSM-3410LINCS
30DrugCentral
Registry NumbersSources
Reaxys:196453Reaxys
CAS:298-81-7KEGG COMPOUND
CAS:298-81-7ChemIDplus
CAS:298-81-7NIST Chemistry WebBook
Citations