Molecule ID: 5574924

IUPAC Name: (1R,3S,6S,10S,11R)-3,12-dimethyl-7-methylidene-2,9-dioxatetracyclo[9.3.0.01,3.06,10]tetradec-12-en-8-one

Description: The molecule is 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 gamma-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. It has a role as an antineoplastic agent and a metabolite. It is an organic heterotetracyclic compound, a gamma-lactone, an epoxide and a sesquiterpene lactone.

SMILES: C=C1C(=O)O[C@@H]2[C@H]3C(C)=CC[C@@]34O[C@@]4(C)CC[C@@H]12

SELFIES: [C][=C][C][=Branch1][C][=O][O][C@@H1][C@H1][C][Branch1][C][C][=C][C][C@@][Ring1][=Branch1][O][C@@][Ring1][Ring1][Branch1][C][C][C][C][C@@H1][Ring1][P][Ring1][=N]

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

Molecular Properties:
- Polar Surface Area: 38.8 Ų
- LogP: 1.7