1.0 2010-04-08 22:08:07 UTC 2025-11-18 23:11:03 UTC FDB008515 Episarsasapogenin Episarsasapogenin, also known as smilagenin or sarsasapogenin, (3beta,5beta,25s)-isomer, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Episarsasapogenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Episarsasapogenin can be found in fenugreek, which makes episarsasapogenin a potential biomarker for the consumption of this food product. (25S)-5-beta-spirostan-3-alpha-ol 3-Episarsasapogenin Episarsasapogenin C27H44O3 416.6365 416.329045274 (1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'R,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol (1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'R,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol 470-03-1 [H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O2 InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18+,19+,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1 GMBQZIIUCVWOCD-RHHRBMONSA-N belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Triterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Triterpenoids Aliphatic heteropolycyclic compounds 3-alpha-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Ketals Oxacyclic compounds Oxanes Secondary alcohols Spirostanes and derivatives Tetrahydrofurans 3-alpha-hydroxysteroid 3-hydroxysteroid Acetal Alcohol Aliphatic heteropolycyclic compound Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Ketal Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Secondary alcohol Spirostane skeleton Steroid Tetrahydrofuran Triterpenoid logp 4.52 ALOGPS logs -7.10 ALOGPS solubility 3.28e-05 g/l ALOGPS melting_point Mp 209-211° logp 5.33 ChemAxon pka_strongest_acidic 18.3 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'R,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol ChemAxon average_mass 416.6365 ChemAxon mono_mass 416.329045274 ChemAxon smiles [H][C@]12C[C@@]3([H])[C@]4([H])CC[C@]5([H])C[C@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O2 ChemAxon formula C27H44O3 ChemAxon inchi InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18+,19+,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1 ChemAxon inchikey GMBQZIIUCVWOCD-RHHRBMONSA-N ChemAxon polar_surface_area 38.69 ChemAxon refractivity 119.42 ChemAxon polarizability 50.86 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 87132 Specdb::MsMs 87133 Specdb::MsMs 87134 Specdb::MsMs 149577 Specdb::MsMs 149578 Specdb::MsMs 149579 Fenugreek Type 1 specific Trigonella foenum-graecum 78534