1.0 2010-04-08 22:05:49 UTC 2019-11-26 02:59:15 UTC FDB003468 Trilobin Constituent of Asimina triloba (pawpaw). Trilobin is found in fruits. Trilobin Trilobine C37H66O7 622.928 622.480854465 (5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-2,5-dihydrofuran-2-one (5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-5H-furan-2-one 165525-53-1 [H][C@](O)(CCCCCCCCCC)[C@@]1([H])CC[C@@]([H])(O1)[C@]([H])(O)CC[C@]([H])(O)[C@]1([H])CC[C@@]([H])(CCCCCCCCCC2=C[C@]([H])(C)OC2=O)O1 InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(38)35-25-26-36(44-35)33(40)23-22-32(39)34-24-21-30(43-34)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30+,31-,32-,33+,34-,35+,36+/m0/s1 VZEPVAAWZDUQLP-FYHSANBVSA-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 Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds 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 Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Secondary alcohol Tetrahydrofuran polyketide logp 6.91 ALOGPS logs -5.97 ALOGPS solubility 6.60e-04 g/l ALOGPS logp 8.68 ChemAxon pka_strongest_acidic 13.28 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (5S)-3-{9-[(2R,5S)-5-[(1S,4R)-1,4-dihydroxy-4-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]butyl]oxolan-2-yl]nonyl}-5-methyl-2,5-dihydrofuran-2-one ChemAxon average_mass 622.928 ChemAxon mono_mass 622.480854465 ChemAxon smiles [H][C@](O)(CCCCCCCCCC)[C@@]1([H])CC[C@@]([H])(O1)[C@]([H])(O)CC[C@]([H])(O)[C@]1([H])CC[C@@]([H])(CCCCCCCCCC2=C[C@]([H])(C)OC2=O)O1 ChemAxon formula C37H66O7 ChemAxon inchi InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(38)35-25-26-36(44-35)33(40)23-22-32(39)34-24-21-30(43-34)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30+,31-,32-,33+,34-,35+,36+/m0/s1 ChemAxon inchikey VZEPVAAWZDUQLP-FYHSANBVSA-N ChemAxon polar_surface_area 105.45 ChemAxon refractivity 176.4 ChemAxon polarizability 77.37 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 3599171 Specdb::MsMs 3599172 Specdb::MsMs 3599173 Specdb::MsMs 3599174 Specdb::MsMs 3599175 Specdb::MsMs 3599176 Fruits Unknown generic