methoxsalen (CHEBI:18358)

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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

Average Mass

216.18950

Monoisotopic Mass

216.04226

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:txid48026)	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.

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

Last Modified

19 June 2017