CHEBI:73228 - arglabin

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ChEBI Name arglabin
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
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Formula C15H18O3
Net Charge 0
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
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.
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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)
Synonyms Sources
(+)-arglabin ChEBI
1β,10β-epoxyguaia-3,11(13)-dien-12,6α-olide ChEBI
Manual Xref Database
US6770673 Patent
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Registry Numbers Types Sources
3549528 Reaxys Registry Number Reaxys
84692-91-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15079907 PubMed citation Europe PMC
17634992 PubMed citation Europe PMC
21997763 PubMed citation Europe PMC
22849854 PubMed citation Europe PMC
8374514 PubMed citation Europe PMC
Last Modified
11 July 2013