CHEBI:28329 - trioxsalen

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ChEBI Name trioxsalen
ChEBI ID CHEBI:28329
Definition 7H-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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1758, CHEBI:20282
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Formula C14H12O3
Net Charge 0
Average Mass 228.24328
Monoisotopic Mass 228.079
InChI InChI=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
InChIKey FMHHVULEAZTJMA-UHFFFAOYSA-N
SMILES Cc1cc2cc3c(C)cc(=O)oc3c(C)c2o1
Roles Classification
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
trioxisaleno ChemIDplus
trioxysalen ChEBI
trioxysalene ChemIDplus
trioxysalenum ChemIDplus
Synonyms Sources
2',4,8-Trimethylpsoralen NIST Chemistry WebBook
4,5',8-Trimethylpsoralen ChemIDplus
4,8,5'-Trimethylpsoralen KEGG COMPOUND
4,8,5'-Trimethylpsoralen KEGG COMPOUND
6-hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactone NIST Chemistry WebBook
Trimethylpsoralen ChemIDplus
Trioxsalen KEGG COMPOUND
Trioxysalen KEGG COMPOUND
Database Links Databases
2759 DrugCentral
C00002502 KNApSAcK
C09314 KEGG COMPOUND
D01034 KEGG DRUG
DB04571 DrugBank
LSM-3223 LINCS
Trioxsalen Wikipedia
US3201421 Patent
View more database links
Registry Numbers Types Sources
221723 Beilstein Registry Number Beilstein
3902-71-4 CAS Registry Number KEGG COMPOUND
3902-71-4 CAS Registry Number NIST Chemistry WebBook
3902-71-4 CAS Registry Number ChemIDplus
Last Modified
22 February 2017