arglabin (CHEBI:73228)

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CHEBI:73228 - arglabin

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ChEBI ID	CHEBI:73228
ChEBI Name	arglabin
Stars
Definition	An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding γ-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the adduct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers.
Last Modified	11 July 2013
Submitter	sjupe
Downloads	Molfile

Formula	C15H18O3
Net Charge	0
Average Mass	246.306
Monoisotopic Mass	246.12559
SMILES	[H][C@]12C(C)=CC[C@@]13O[C@@]3(C)CC[C@H]1C(=C)C(=O)O[C@@H]12
InChI	InChI=1S/C15H18O3/c1-8-4-7-15-11(8)12-10(9(2)13(16)17-12)5-6-14(15,3)18-15/h4,10-12H,2,5-7H2,1,3H3/t10-,11+,12-,14-,15+/m0/s1
InChIKey	UVJYAKBJSGRTHA-CUZKYEQNSA-N

Roles Classification

Biological Role:	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	arglabin (CHEBI:73228) has role antineoplastic agent (CHEBI:35610)
	arglabin (CHEBI:73228) has role metabolite (CHEBI:25212)
	arglabin (CHEBI:73228) is a epoxide (CHEBI:32955)
	arglabin (CHEBI:73228) is a organic heterotetracyclic compound (CHEBI:38163)
	arglabin (CHEBI:73228) is a sesquiterpene lactone (CHEBI:37667)
	arglabin (CHEBI:73228) is a γ-lactone (CHEBI:37581)
Incoming Relation(s)
Incoming Relation(s)	arborescin (CHEBI:73226) has functional parent arglabin (CHEBI:73228)

IUPAC Name
(3aR,4aS,6aS,9aS,9bR)-1,4a-dimethyl-7-methylene-5,6,6a,7,9a,9b-hexahydro-3H-oxireno[8,8a]azuleno[4,5-b]furan-8(4aH)-one

Synonyms	Source
(+)-arglabin	ChEBI
1β,10β-epoxyguaia-3,11(13)-dien-12,6α-olide	ChEBI

Manual Xrefs	Databases
US6770673	Patent

Registry Numbers	Sources
Reaxys:3549528	Reaxys
CAS:84692-91-1	ChemIDplus

Citations