1.0 2010-04-08 22:04:54 UTC 2019-11-26 02:56:11 UTC FDB001257 Squamosten A Isolated from the seeds of Annona squamosa (sugar apple). Squamosten A is found in fruits. C37H66O7 622.9157 622.480854466 5-methyl-3-(2,10,13-trihydroxy-13-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}tridecyl)-2,5-dihydrofuran-2-one 5-methyl-3-(2,10,13-trihydroxy-13-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}tridecyl)-5H-furan-2-one 155834-22-3 CCCCCCCCCC\C=C/CCC(O)C1CCC(O1)C(O)CCC(O)CCCCCCCC(O)CC1=CC(C)OC1=O InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-33(40)35-25-26-36(44-35)34(41)24-23-31(38)20-17-14-13-15-18-21-32(39)28-30-27-29(2)43-37(30)42/h12,16,27,29,31-36,38-41H,3-11,13-15,17-26,28H2,1-2H3/b16-12- XHKLAUPULLMCQU-VBKFSLOCSA-N belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Annonaceous acetogenins Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty alcohols Aliphatic heteromonocyclic compounds Butenolides Carbonyl compounds Dialkyl ethers Enoate esters Hydrocarbon derivatives Lactones Long-chain fatty alcohols Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Polyols Secondary alcohols Tetrahydrofurans 2-furanone Alcohol Aliphatic heteromonocyclic compound Alpha,beta-unsaturated carboxylic ester Annonaceae acetogenin skeleton Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dialkyl ether Dihydrofuran Enoate ester Ether Hydrocarbon derivative Lactone Long chain fatty alcohol Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Polyol Secondary alcohol Tetrahydrofuran logp 6.97 ALOGPS logs -5.78 ALOGPS solubility 1.04e-03 g/l ALOGPS melting_point Mp 64-67° logp 8.23 ChemAxon pka_strongest_acidic 13.83 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac 5-methyl-3-(2,10,13-trihydroxy-13-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}tridecyl)-2,5-dihydrofuran-2-one ChemAxon average_mass 622.9157 ChemAxon mono_mass 622.480854466 ChemAxon smiles CCCCCCCCCC\C=C/CCC(O)C1CCC(O1)C(O)CCC(O)CCCCCCCC(O)CC1=CC(C)OC1=O ChemAxon formula C37H66O7 ChemAxon inchi InChI=1S/C37H66O7/c1-3-4-5-6-7-8-9-10-11-12-16-19-22-33(40)35-25-26-36(44-35)34(41)24-23-31(38)20-17-14-13-15-18-21-32(39)28-30-27-29(2)43-37(30)42/h12,16,27,29,31-36,38-41H,3-11,13-15,17-26,28H2,1-2H3/b16-12- ChemAxon inchikey XHKLAUPULLMCQU-VBKFSLOCSA-N ChemAxon polar_surface_area 116.45 ChemAxon refractivity 179.66 ChemAxon polarizability 77.11 ChemAxon rotatable_bond_count 27 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 13952 Specdb::CMs 41673 Specdb::CMs 547253 Specdb::CMs 547254 Specdb::CMs 547255 Specdb::CMs 547256 Specdb::CMs 547257 Specdb::CMs 547258 Specdb::CMs 547259 Specdb::CMs 547260 Specdb::CMs 547261 Specdb::CMs 547262 Specdb::CMs 547263 Specdb::CMs 547264 Specdb::CMs 547265 Specdb::CMs 547266 Specdb::CMs 547267 Specdb::CMs 547268 Specdb::CMs 547269 Specdb::CMs 547270 Specdb::CMs 547271 Specdb::CMs 547272 Specdb::CMs 547273 Specdb::CMs 547274 Specdb::CMs 547275 Specdb::MsMs 54594 Specdb::MsMs 54595 Specdb::MsMs 54596 Specdb::MsMs 116301 Specdb::MsMs 116302 Specdb::MsMs 116303 Specdb::MsMs 2845211 Specdb::MsMs 2845212 Specdb::MsMs 2845213 Specdb::MsMs 2861206 Specdb::MsMs 2861207 Specdb::MsMs 2861208 HMDB29970 Fruits Unknown generic