Molecule ID: 24899923

IUPAC Name: (E)-5-[(1R,2R,4aR,5R,8aS)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid

Description: The molecule is a labdane diterpenoid that is labdane with a double bond at position 13 and is substituted by hydroxy groups at positions 8alpha and 19 and a carboxy group at position 15. Isolated from the aerial parts of Crassocephalum mannii, it exhibits inhibitory activity towards cyclooxygenases (COX-1 and COX-2). It has a role as a cyclooxygenase 1 inhibitor, a cyclooxygenase 2 inhibitor and a plant metabolite. It is a labdane diterpenoid, a diol and an alpha,beta-unsaturated monocarboxylic acid.

SMILES: C/C(=C\C(=O)O)CC[C@@H]1[C@@]2(C)CCC[C@@](C)(CO)[C@@H]2CC[C@@]1(C)O

SELFIES: [C][/C][=Branch1][#Branch1][=C][\C][=Branch1][C][=O][O][C][C][C@@H1][C@@][Branch1][C][C][C][C][C][C@@][Branch1][C][C][Branch1][Ring1][C][O][C@@H1][Ring1][#Branch2][C][C][C@@][Ring1][=C][Branch1][C][C][O]

InChI: InChI=1S/C20H34O4/c1-14(12-17(22)23)6-7-16-19(3)10-5-9-18(2,13-21)15(19)8-11-20(16,4)24/h12,15-16,21,24H,5-11,13H2,1-4H3,(H,22,23)/b14-12+/t15-,16+,18-,19-,20+/m0/s1

Molecular Properties:
- Polar Surface Area: 77.8 Ų
- LogP: 3.9