1.0 2010-04-08 22:09:39 UTC 2025-11-18 23:27:53 UTC FDB011460 12,15-cis-Squamostatin A Constituent of the seeds of Annona atemoya (custard apple). Cytotoxic. 12,15-cis-Squamostatin A is found in fruits. 12,15-cis-Squamostatin A C37H66O8 638.9151 638.475769088 3-[9-(5-{4-[5-(1,5-dihydroxyundecyl)oxolan-2-yl]-1,4-dihydroxybutyl}oxolan-2-yl)nonyl]-5-methyl-2,5-dihydrofuran-2-one 3-[9-(5-{4-[5-(1,5-dihydroxyundecyl)oxolan-2-yl]-1,4-dihydroxybutyl}oxolan-2-yl)nonyl]-5-methyl-5H-furan-2-one CCCCCCC(O)CCCC(O)C1CCC(O1)C(O)CCC(O)C1CCC(CCCCCCCCCC2=CC(C)OC2=O)O1 InChI=1S/C37H66O8/c1-3-4-5-12-16-29(38)17-14-19-31(39)35-24-25-36(45-35)33(41)22-21-32(40)34-23-20-30(44-34)18-13-10-8-6-7-9-11-15-28-26-27(2)43-37(28)42/h26-27,29-36,38-41H,3-25H2,1-2H3 HKIHGTSLUYNNHM-UHFFFAOYSA-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 logp 5.73 ALOGPS logs -5.54 ALOGPS solubility 1.85e-03 g/l ALOGPS logp 7.3 ChemAxon pka_strongest_acidic 13.7 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac 3-[9-(5-{4-[5-(1,5-dihydroxyundecyl)oxolan-2-yl]-1,4-dihydroxybutyl}oxolan-2-yl)nonyl]-5-methyl-2,5-dihydrofuran-2-one ChemAxon average_mass 638.9151 ChemAxon mono_mass 638.475769088 ChemAxon smiles CCCCCCC(O)CCCC(O)C1CCC(O1)C(O)CCC(O)C1CCC(CCCCCCCCCC2=CC(C)OC2=O)O1 ChemAxon formula C37H66O8 ChemAxon inchi InChI=1S/C37H66O8/c1-3-4-5-12-16-29(38)17-14-19-31(39)35-24-25-36(45-35)33(41)22-21-32(40)34-23-20-30(44-34)18-13-10-8-6-7-9-11-15-28-26-27(2)43-37(28)42/h26-27,29-36,38-41H,3-25H2,1-2H3 ChemAxon inchikey HKIHGTSLUYNNHM-UHFFFAOYSA-N ChemAxon polar_surface_area 125.68 ChemAxon refractivity 178.07 ChemAxon polarizability 77.76 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 8036 Specdb::MsMs 8037 Specdb::MsMs 8038 Specdb::MsMs 14708 Specdb::MsMs 14709 Specdb::MsMs 14710 Specdb::MsMs 2388701 Specdb::MsMs 2388702 Specdb::MsMs 2388703 Specdb::MsMs 2574451 Specdb::MsMs 2574452 Specdb::MsMs 2574453 Specdb::CMs 9872 Specdb::CMs 601557 Specdb::CMs 601558 Specdb::CMs 601559 Specdb::CMs 601560 Specdb::CMs 601561 Specdb::CMs 601562 Specdb::CMs 601563 Specdb::CMs 601564 Specdb::CMs 601565 Specdb::CMs 601566 Specdb::CMs 601567 Specdb::CMs 601568 Specdb::CMs 601569 Specdb::CMs 601570 Specdb::CMs 601571 Specdb::CMs 601572 Specdb::CMs 601573 Specdb::CMs 601574 Specdb::CMs 601575 Specdb::CMs 601576 Specdb::CMs 601577 Specdb::CMs 601578 Specdb::CMs 601579 Specdb::CMs 601580 HMDB0033423 Fruits Unknown generic