arglabin (CHEBI:73228)

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ChEBI Name	arglabin

ChEBI ID	CHEBI:73228

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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Steve Jupe

Supplier Information

Download	Molfile XML SDF

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Formula

C15H18O3

Net Charge

Average Mass

246.30160

Monoisotopic Mass

246.12559

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

SMILES

[H][C@@]12[C@H]3OC(=O)C(=C)[C@@H]3CC[C@]3(C)O[C@]13CC=C2C

Roles Classification
Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	arglabin (CHEBI:73228) has role antineoplastic agent (CHEBI:35610) arglabin (CHEBI:73228) has role metabolite (CHEBI:25212) arglabin (CHEBI:73228) is a γ-lactone (CHEBI:37581) 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)

Incoming	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

Last Modified

11 July 2013