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CHEBI:28329 - trioxsalen

ChEBI IDCHEBI:28329
ChEBI Nametrioxsalen
Stars
Definition7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis.
Secondary ChEBI IDsCHEBI:1758, CHEBI:20282
Last Modified22 February 2017
DownloadsMolfile
FormulaC14H12O3
Net Charge0
Average Mass228.247
Monoisotopic Mass228.07864
SMILESCc1cc2cc3c(C)cc(=O)oc3c(C)c2o1
InChIInChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3
InChIKeyFMHHVULEAZTJMA-UHFFFAOYSA-N
Wikipedia
Roles Classification
Applications:
dermatologic drug  A drug used to treat or prevent skin disorders or for the routine care of skin.
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)
trioxsalen (CHEBI:28329) has role dermatologic drug (CHEBI:50177)
trioxsalen (CHEBI:28329) has role photosensitizing agent (CHEBI:47868)
trioxsalen (CHEBI:28329) is a psoralens (CHEBI:26369)
IUPAC Name 
2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
INNs  Source
trioxysalenChEBI
trioxisalenoChemIDplus
trioxysalenumChemIDplus
trioxysaleneChemIDplus
Synonyms  Source
4,8,5'-TrimethylpsoralenKEGG COMPOUND
TrioxsalenKEGG COMPOUND
TrioxysalenKEGG COMPOUND
4,5',8-TrimethylpsoralenChemIDplus
TrimethylpsoralenChemIDplus
6-hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactoneNIST Chemistry WebBook
Manual XrefsDatabases
C09314KEGG COMPOUND
DB04571DrugBank
US3201421Patent
D01034KEGG DRUG
TrioxsalenWikipedia
C00002502KNApSAcK
LSM-3223LINCS
2759DrugCentral
Registry NumbersSources
Beilstein:221723Beilstein
CAS:3902-71-4KEGG COMPOUND
CAS:3902-71-4ChemIDplus
CAS:3902-71-4NIST Chemistry WebBook