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CHEBI:18358 - methoxsalen

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name methoxsalen
ChEBI ID CHEBI:18358
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40342, CHEBI:29040, CHEBI:101063, CHEBI:10068, CHEBI:12268, CHEBI:12715, CHEBI:27330, CHEBI:27331, CHEBI:21960
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Formula C12H8O4
Net Charge 0
Average Mass 216.18950
Monoisotopic Mass 216.042
InChI InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChIKey QXKHYNVANLEOEG-UHFFFAOYSA-N
SMILES COc1c2occc2cc2ccc(=O)oc12
Metabolite of Species Details
Ammi majus (NCBI:48026) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): 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.
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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 5-hydroxyxanthotoxin (CHEBI:2082) has functional parent methoxsalen (CHEBI:18358)
IUPAC Name
9-methoxy-7H-furo[3,2-g]chromen-7-one
Synonyms Sources
6-hydroxy-7-methoxy-5-benzofuranacrylic acid δ-lactone NIST Chemistry WebBook
8-methoxy-2',3',6,7-furocoumarin ChemIDplus
8-methoxy-4',5':6,7-furocoumarin NIST Chemistry WebBook
8-methoxy-[furano-3'.2':6.7-coumarin] ChemIDplus
8-Methoxyfuranocoumarin KEGG COMPOUND
8-methoxypsoralen ChemIDplus
8-Methoxypsoralen KEGG COMPOUND
8-MOP ChemIDplus
8-MP NIST Chemistry WebBook
9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one NIST Chemistry WebBook
Methoxsalen KEGG COMPOUND
METHOXSALEN PDBeChem
O-methylxanthotoxol ChEBI
O-Methylxanthotoxol KEGG COMPOUND
Xanthotoxin KEGG COMPOUND
xanthotoxin UniProt
Brand Names Sources
Meladinine DrugBank
Meloxine ChemIDplus
Oxsoralen DrugBank
Ultra Mop DrugBank
Uvadex DrugBank
Database Links Databases
8MO PDBeChem
C00000576 KNApSAcK
C01864 KEGG COMPOUND
D00139 KEGG DRUG
DB00553 DrugBank
HMDB14693 HMDB
LSM-3410 LINCS
Methoxsalen Wikipedia
US2889337 Patent
View more database links
Registry Numbers Types Sources
196453 Beilstein Registry Number Beilstein
196453 Reaxys Registry Number Reaxys
298-81-7 CAS Registry Number ChemIDplus
298-81-7 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
15009205 PubMed citation Europe PMC
7945434 PubMed citation Europe PMC
Last Modified
25 February 2016