1.0 2011-09-21 00:41:17 UTC 2015-07-21 06:58:01 UTC FDB024201 CPA(18:2(9Z,12Z)/0:0) cPA(18:2(9Z,12Z)/0:0) is a cyclic phosphatidic acid or cyclic lysophosphatidic acid. It is a glycerophospholipid in which a cyclic phosphate moiety occupies two glycerol substitution sites. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1). Fatty acids containing 16 and 18 carbons are the most common. Cyclic phosphatidic acids have been detected in a wide range of organisms including humans, especially in the brain but also in serum (at a concentration of 10-7M). cPA's have a cyclic phosphate at the sn-2 and sn-3 positions of the glycerol carbons, and this structure is absolutely necessary for their activities. In particular, it is found in tissues subject to injury, and while it may have some similar signalling functions to lysophosphatidic acid per se, it also has some quite distinct biological activities. For example, cyclic phosphatidic acid is known to be a specific inhibitor of DNA polymerase alpha. It has an appreciable effect on the inhibition of cancer cell invasion and metastasis. [HMDB] 1-(9Z,12Z-Octadecadienoyl)-cycloatidic acid 1-(9Z,12Z-octadecadienoyl)-cyclophosphatidic acid 1-Linoleoyl-glycero-3-cycloate 1-linoleoyl-glycero-3-cyclophosphate cPA(18:2) cPA(18:2/0:0) cPA(18:2n6/0:0) cPA(18:2w6/0:0) Cyclic atidic acid(18:2) Cyclic atidic acid(18:2/0:0) Cyclic atidic acid(18:2N6/0:0) Cyclic atidic acid(18:2W6/0:0) Cyclic Phosphatidic acid(18:2) Cyclic Phosphatidic acid(18:2/0:0) Cyclic Phosphatidic acid(18:2n6/0:0) Cyclic Phosphatidic acid(18:2w6/0:0) C21H37O6P 416.4886 416.232775428 (2-hydroxy-2-oxo-1,3,2lambda5-dioxaphospholan-4-yl)methyl octadeca-9,12-dienoate (2-hydroxy-2-oxo-1,3,2lambda5-dioxaphospholan-4-yl)methyl octadeca-9,12-dienoate CCCCCC=CCC=CCCCCCCCC(=O)OCC1COP(O)(=O)O1 InChI=1S/C21H37O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h6-7,9-10,20H,2-5,8,11-19H2,1H3,(H,23,24) AZRMIMGGEACCGU-UHFFFAOYSA-N belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Lineolic acids and derivatives Organic compounds Lipids and lipid-like molecules Fatty Acyls Lineolic acids and derivatives Aliphatic heteromonocyclic compounds 1-acyl-sn-glycerol-2,3-cyclic-phosphates Carbonyl compounds Carboxylic acid esters Dioxaphospholanes Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organic phosphoric acids and derivatives Oxacyclic compounds 1,3_dioxaphospholane 1-acyl-sn-glycerol-2,3-cyclic-phosphate Aliphatic heteromonocyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Hydrocarbon derivative Monoacylglycerophosphate Monocarboxylic acid or derivatives Octadecanoid Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organoheterocyclic compound Organooxygen compound Oxacycle Solid logp 5.47 ALOGPS logs -5.15 ALOGPS solubility 2.96e-03 g/l ALOGPS logp 6.02 ChemAxon pka_strongest_acidic 1.84 ChemAxon pka_strongest_basic -7 ChemAxon iupac (2-hydroxy-2-oxo-1,3,2lambda5-dioxaphospholan-4-yl)methyl octadeca-9,12-dienoate ChemAxon average_mass 416.4886 ChemAxon mono_mass 416.232775428 ChemAxon smiles CCCCCC=CCC=CCCCCCCCC(=O)OCC1COP(O)(=O)O1 ChemAxon formula C21H37O6P ChemAxon inchi InChI=1S/C21H37O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(22)25-18-20-19-26-28(23,24)27-20/h6-7,9-10,20H,2-5,8,11-19H2,1H3,(H,23,24) ChemAxon inchikey AZRMIMGGEACCGU-UHFFFAOYSA-N ChemAxon polar_surface_area 82.06 ChemAxon refractivity 112.64 ChemAxon polarizability 46.43 ChemAxon rotatable_bond_count 17 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon HMDB07007 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823