Isocupressic acid

Isocupressic acid is a diterpene acid present in a variety of conifer needles. It induces abortion in cattle.^[1] It is found in all parts of the ponderosa pine (Pinus ponderosa), especially the needles. This gives its toxic and abortifacient effects.^[2] It is also present in the lodgepole pine (P. contorta), the jeffrey pine (P. jeffreyi) and possibly in the monterey pine (P. radiata).^[3]

Isocupressic acid

Names
IUPAC name (13E)-15-Hydroxylabda-8(20),13-dien-19-oic acid
Systematic IUPAC name (1S,4aR,5S,8aR)-5-[(3E)-5-Hydroxy-3-methylpent-3-en-1-yl]-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylic acid
Identifiers
CAS Number	1909-91-7 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL511193
ChemSpider	4942630
PubChem CID	6438138
UNII	6DV5EL78HE Y
CompTox Dashboard (EPA)	DTXSID901045341
InChI InChI=1S/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)/b14-10+/t16-,17+,19+,20-/m0/s1 Key: DOYKMKZYLAAOGH-DOEMEAPXSA-N InChI=1/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)/b14-10+/t16-,17+,19+,20-/m0/s1 Key: DOYKMKZYLAAOGH-DOEMEAPXBD
SMILES O=C(O)[C@]1(CCC[C@@]2([C@H](/C(=C)CC[C@@H]12)CCC(=C/CO)/C)C)C
Properties
Chemical formula	C20H32O3
Molar mass	320.473 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references