1.02010-04-08 22:10:18 UTC2019-11-26 03:07:23 UTCFDB012684TigogeninTigogenin, also known as sarsasapogenin, (3beta,5alpha,25s)-isomer or smilagenin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, tigogenin is considered to be a sterol lipid molecule. Tigogenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Tigogenin can be found in fenugreek, which makes tigogenin a potential biomarker for the consumption of this food product. 22-Isoallospirostan-3b-olTigogeninC27H44O3416.6365416.329045274(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-oltigogenin77-60-1[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)O2InChI=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-/m1/s1GMBQZIIUCVWOCD-MFRNJXNGSA-N belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.TriterpenoidsOrganic compoundsLipids and lipid-like moleculesPrenol lipidsTriterpenoidsAliphatic heteropolycyclic compounds3-beta-hydroxysteroidsCyclic alcohols and derivativesHydrocarbon derivativesKetalsOxacyclic compoundsOxanesSecondary alcoholsSpirostanes and derivativesTetrahydrofurans3-beta-hydroxysteroid3-hydroxysteroidAcetalAlcoholAliphatic heteropolycyclic compoundCyclic alcoholHydrocarbon derivativeHydroxysteroidKetalOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxaneSecondary alcoholSpirostane skeletonSteroidTetrahydrofuranTriterpenoidSpirostan and derivativesSpirostanols and derivativesspirostantriterpenoidlogp4.52logs-7.10solubility3.28e-05 g/lmelting_pointMp 205-206°logp5.33pka_strongest_acidic18.3pka_strongest_basic-1.4iupac(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-olaverage_mass416.6365mono_mass416.329045274smiles[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)O2formulaC27H44O3inchiInChI=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-/m1/s1inchikeyGMBQZIIUCVWOCD-MFRNJXNGSA-Npolar_surface_area38.69refractivity119.42polarizability50.97rotatable_bond_count0acceptor_count3donor_count1physiological_charge0formal_charge0Specdb::MsMs58824Specdb::MsMs58825Specdb::MsMs58826Specdb::MsMs114840Specdb::MsMs114841Specdb::MsMs114842FenugreekType 1specificTrigonella foenum-graecum78534antitumor672A substance that inhibits or prevents the proliferation of neoplasms.