1.0 2010-04-08 22:14:11 UTC 2025-11-19 02:17:35 UTC FDB019178 12alpha-Hydroxy-13,18-dehydroparain Constituent of Quassia amara (Surinam quassia) 12a-Hydroxy-13,18-dehyroparain C21H28O6 376.4434 376.188588628 15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione 15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione COC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O InChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3 CKRHSGZMMGXRKZ-UHFFFAOYSA-N belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Quassinoids Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds 1,2-diols Carboxylic acid esters Cyclic alcohols and derivatives Cyclohexenones Delta valerolactones Hydrocarbon derivatives Monocarboxylic acids and derivatives Naphthalenes Naphthopyrans Organic oxides Oxacyclic compounds Oxanes Pyrans Secondary alcohols 1,2-diol Alcohol Aliphatic heteropolycyclic compound C-20 quassinoid skeleton Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic alcohol Cyclohexenone Delta valerolactone Delta_valerolactone Hydrocarbon derivative Ketone Lactone Monocarboxylic acid or derivatives Naphthalene Naphthopyran Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Pyran Quassinoid Secondary alcohol logp 1.01 ALOGPS logs -2.42 ALOGPS solubility 1.43e+00 g/l ALOGPS melting_point Mp 238-241° logp 1.03 ChemAxon pka_strongest_acidic 13.41 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 15,16-dihydroxy-4-methoxy-2,6,17-trimethyl-14-methylidene-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-ene-3,11-dione ChemAxon average_mass 376.4434 ChemAxon mono_mass 376.188588628 ChemAxon smiles COC1=CC(C)C2CC3OC(=O)CC4C(=C)C(O)C(O)C(C34C)C2(C)C1=O ChemAxon formula C21H28O6 ChemAxon inchi InChI=1S/C21H28O6/c1-9-6-13(26-5)19(25)21(4)11(9)7-14-20(3)12(8-15(22)27-14)10(2)16(23)17(24)18(20)21/h6,9,11-12,14,16-18,23-24H,2,7-8H2,1,3-5H3 ChemAxon inchikey CKRHSGZMMGXRKZ-UHFFFAOYSA-N ChemAxon polar_surface_area 93.06 ChemAxon refractivity 98.57 ChemAxon polarizability 39.19 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26471 Specdb::CMs 46456 Specdb::CMs 151399 Specdb::MsMs 87024 Specdb::MsMs 87025 Specdb::MsMs 87026 Specdb::MsMs 149442 Specdb::MsMs 149443 Specdb::MsMs 149444 Specdb::MsMs 2334223 Specdb::MsMs 2334224 Specdb::MsMs 2334225 Specdb::MsMs 2627591 Specdb::MsMs 2627592 Specdb::MsMs 2627593 HMDB39557 #<Reference:0x000055ce32511930>