1.0 2010-04-08 22:09:13 UTC 2025-11-18 23:20:54 UTC FDB010617 Glabracin B Constituent of the leaves of Annona glabra (pond apple). Glabracin B is found in alcoholic beverages and fruits. Glabracin B C37H66O8 638.9151 638.475769088 3-(8-{5-[5-(5,6-dihydroxyhexadecyl)oxolan-2-yl]oxolan-2-yl}-2,8-dihydroxyoctyl)-5-methyl-2,5-dihydrofuran-2-one 3-(8-{5-[5-(5,6-dihydroxyhexadecyl)oxolan-2-yl]oxolan-2-yl}-2,8-dihydroxyoctyl)-5-methyl-5H-furan-2-one CCCCCCCCCCC(O)C(O)CCCCC1CCC(O1)C1CCC(O1)C(O)CCCCCC(O)CC1=CC(C)OC1=O InChI=1S/C37H66O8/c1-3-4-5-6-7-8-9-12-18-31(39)32(40)19-15-14-17-30-21-22-35(44-30)36-24-23-34(45-36)33(41)20-13-10-11-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3 CXWUDOBKRFRXAX-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 5.83 ALOGPS logs -5.60 ALOGPS solubility 1.62e-03 g/l ALOGPS logp 7.3 ChemAxon pka_strongest_acidic 13.7 ChemAxon pka_strongest_basic -2.7 ChemAxon iupac 3-(8-{5-[5-(5,6-dihydroxyhexadecyl)oxolan-2-yl]oxolan-2-yl}-2,8-dihydroxyoctyl)-5-methyl-2,5-dihydrofuran-2-one ChemAxon average_mass 638.9151 ChemAxon mono_mass 638.475769088 ChemAxon smiles CCCCCCCCCCC(O)C(O)CCCCC1CCC(O1)C1CCC(O1)C(O)CCCCCC(O)CC1=CC(C)OC1=O ChemAxon formula C37H66O8 ChemAxon inchi InChI=1S/C37H66O8/c1-3-4-5-6-7-8-9-12-18-31(39)32(40)19-15-14-17-30-21-22-35(44-30)36-24-23-34(45-36)33(41)20-13-10-11-16-29(38)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3 ChemAxon inchikey CXWUDOBKRFRXAX-UHFFFAOYSA-N ChemAxon polar_surface_area 125.68 ChemAxon refractivity 178.07 ChemAxon polarizability 78.6 ChemAxon rotatable_bond_count 25 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21391 Specdb::CMs 601509 Specdb::CMs 601510 Specdb::CMs 601511 Specdb::CMs 601512 Specdb::CMs 601513 Specdb::CMs 601514 Specdb::CMs 601515 Specdb::CMs 601516 Specdb::CMs 601517 Specdb::CMs 601518 Specdb::CMs 601519 Specdb::CMs 601520 Specdb::CMs 601521 Specdb::CMs 601522 Specdb::CMs 601523 Specdb::CMs 601524 Specdb::CMs 601525 Specdb::CMs 601526 Specdb::CMs 601527 Specdb::CMs 601528 Specdb::CMs 601529 Specdb::CMs 601530 Specdb::CMs 601531 Specdb::CMs 601532 Specdb::MsMs 85698 Specdb::MsMs 85699 Specdb::MsMs 85700 Specdb::MsMs 147837 Specdb::MsMs 147838 Specdb::MsMs 147839 Specdb::MsMs 2405915 Specdb::MsMs 2405916 Specdb::MsMs 2405917 Specdb::MsMs 2529570 Specdb::MsMs 2529571 Specdb::MsMs 2529572 HMDB32113 #<Reference:0x000055ce334e6068> Alcoholic beverages Unknown generic Fruits Unknown generic