1.0 2010-04-08 22:10:45 UTC 2019-11-26 03:08:31 UTC FDB013515 Cucurbitacin B Together wth other cucurbitacins, is responsible for the bitter taste and toxic props. of spoilt cucumbers. Cucurbitacin B is found in many foods, some of which are muskmelon, bitter gourd, green vegetables, and cucumber. Amarin? Cucurbitacin B Cucurbitacine (b) Datisca principle b Datiscn principle b C32H46O8 558.7028 558.319268448 (3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate cucurbitacin B 6199-67-3 CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+ IXQKXEUSCPEQRD-OUKQBFOZSA-N belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitacins Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Cucurbitacins Aliphatic homopolycyclic compounds 11-oxosteroids 16-hydroxysteroids 3-oxo delta-5-steroids Acryloyl compounds Acyloins Alpha-hydroxy ketones Carboxylic acid esters Cyclic alcohols and derivatives Cyclic ketones Delta-5-steroids Enones Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Secondary alcohols Steroid esters Tertiary alcohols Triterpenoids 11-oxosteroid 16-hydroxysteroid 2-hydroxysteroid 20-hydroxysteroid 21-oxosteroid 22-oxosteroid 3-oxo-delta-5-steroid 3-oxosteroid Acryloyl-group Acyloin Alcohol Aliphatic homopolycyclic compound Alpha,beta-unsaturated ketone Alpha-hydroxy ketone Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cucurbitacin skeleton Cyclic alcohol Cyclic ketone Delta-5-steroid Enone Hydrocarbon derivative Hydroxysteroid Ketone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol Steroid ester Tertiary alcohol Triterpenoid logp 3.70 ALOGPS logs -5.00 ALOGPS solubility 5.56e-03 g/l ALOGPS melting_point Mp 180-182° logp 3.13 ChemAxon pka_strongest_acidic 12.8 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate ChemAxon average_mass 558.7028 ChemAxon mono_mass 558.319268448 ChemAxon smiles CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C ChemAxon formula C32H46O8 ChemAxon inchi InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+ ChemAxon inchikey IXQKXEUSCPEQRD-OUKQBFOZSA-N ChemAxon polar_surface_area 138.2 ChemAxon refractivity 151.04 ChemAxon polarizability 60.69 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14600 Specdb::CMs 44088 Specdb::CMs 281961 Specdb::CMs 342903 Specdb::CMs 342904 Specdb::CMs 342905 Specdb::CMs 342906 Specdb::CMs 342907 Specdb::CMs 342908 Specdb::CMs 342909 Specdb::CMs 342910 Specdb::CMs 342911 Specdb::CMs 342912 Specdb::CMs 342913 Specdb::CMs 342914 Specdb::CMs 342915 Specdb::CMs 342916 Specdb::CMs 342917 Specdb::CMs 342918 Specdb::CMs 342919 Specdb::CMs 342920 Specdb::CMs 342921 Specdb::CMs 342922 Specdb::CMs 342923 Specdb::CMs 342924 Specdb::MsMs 62931 Specdb::MsMs 62932 Specdb::MsMs 62933 Specdb::MsMs 119769 Specdb::MsMs 119770 Specdb::MsMs 119771 Specdb::MsMs 2676732 Specdb::MsMs 2676733 Specdb::MsMs 2676734 Specdb::MsMs 3028269 Specdb::MsMs 3028270 Specdb::MsMs 3028271 HMDB34927 #<Reference:0x000055ce332f0b50> Bitter gourd Type 1 specific Momordica charantia 3673 Calabash Type 1 specific Lagenaria siceraria 3668 Cucumber Type 1 specific Cucumis sativus 3659 Green vegetables Unknown generic Muskmelon Type 1 specific Cucumis melo 3656 Towel gourd Type 1 specific Luffa aegyptiaca 3670 Watermelon Type 1 specific Citrullus lanatus 3654 bitter Anti gibberellin 297 A substance that diminishes the rate of a chemical reaction. Anti hepatotoxic 328 Any compound that is able to prevent damage to the liver. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Insectifuge 1041 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. Insectiphile 1042 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.