1.02010-04-08 22:10:20 UTC2019-11-26 03:07:29 UTCFDB012734DiosgeninDiosgenin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Diosgenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Diosgenin can be found in a number of food items such as carrot, wild carrot, yam, and bitter gourd, which makes diosgenin a potential biomarker for the consumption of these food products. Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro. The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products .(25R)-Spirost-5-en-3β-ol(25R)-Spirost-5-en-3b-ol«delta»22α-Spirost-5-en-3β-ol25d-Spirost-5-en-3b-ol5,20a,22a,25D-spirosten-3β-ol5,20alpha,22alpha,25D-Spirosten-3 beta-olDioscorea sapogeninDiosgeninNitogeninSpirost-5-en-3-olSpirost-5-en-3-ol deriv.Spirost-5-en-3-ol, (3β,25R)-Spirost-5-en-3-ol, (3b,25R)-Spirost-5-en-3α-Spirost-5-en-3β-olSpirost-5-en-3β-ol, (25R)-Spirost-5-en-3b-ol, (25R)-C27H42O3414.6206414.31339521(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol512-04-9CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO1InChI=1S/C27H42O3/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/h5,16-17,19-24,28H,6-15H2,1-4H3WQLVFSAGQJTQCK-UHFFFAOYSA-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-hydroxy delta-5-steroids3-beta-hydroxysteroidsCyclic alcohols and derivativesDelta-5-steroidsHydrocarbon derivativesKetalsOxacyclic compoundsOxanesSecondary alcoholsSpirostanes and derivativesTetrahydrofurans3-beta-hydroxy-delta-5-steroid3-beta-hydroxysteroid3-hydroxy-delta-5-steroid3-hydroxysteroidAcetalAlcoholAliphatic heteropolycyclic compoundCyclic alcoholDelta-5-steroidHydrocarbon derivativeHydroxysteroidKetalOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxaneSecondary alcoholSpirostane skeletonSteroidTetrahydrofuranTriterpenoid3beta-sterolSpirostan and derivativesSpirostanols and derivativeshexacyclic triterpenoidsapogeninspiroketalspirostanlogp4.15logs-5.88solubility5.52e-04 g/lmelting_pointMp 204-207°logp4.93pka_strongest_acidic18.2pka_strongest_basic-1.4iupac(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-olaverage_mass414.6206mono_mass414.31339521smilesCC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO1formulaC27H42O3inchiInChI=1S/C27H42O3/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/h5,16-17,19-24,28H,6-15H2,1-4H3inchikeyWQLVFSAGQJTQCK-UHFFFAOYSA-Npolar_surface_area38.69refractivity120.27polarizability50.68rotatable_bond_count0acceptor_count3donor_count1physiological_charge0formal_charge0495816AsparagusType 1specificAsparagus officinalis4686Bitter gourdType 1specificMomordica charantia3673CarrotType 1specificDaucus carota ssp. sativus79200570.0570.0570.0mg/100 gFenugreekType 1specificTrigonella foenum-graecum785341115.01115.01115.0mg/100 gWild carrotType 1specificDaucus carota4039570.0570.0570.0mg/100 gYamType 1specificDioscorea4672anti fatigue274Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti inflammatory370A substance that reduces or suppresses inflammation.anti neoplastic465A substance that inhibits or prevents the proliferation of neoplasms.anti stress632Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti viral689A substance that destroys or inhibits replication of viruses.estrogenic922hepatoprotective981Any compound that is able to prevent damage to the liver.hypocholesterolemic1016mastogenic1092