Compound: DIOSGENIN
SMILES: O1[C@@]2(O[C@H]3C[C@H]4[C@H]5[C@@H]([C@@]6(C(C[C@@H](O)CC6)=CC5)C)CC[C@@]4([C@H]3[C@@H]2C)C)CC[C@H](C1)C
InChIKey: WQLVFSAGQJTQCK-VKROHFNGSA-N
Synonyms: DIOSGENIN, 512-04-9, Nitogenin, (3beta,25R)-spirost-5-en-3-ol, K49P2K8WLX, CHEBI:4629, DTXSID00895074, (25R)-spirost-5-en-3beta-diol, Spirost-5-en-3-ol, (3beta,25R)-, NSC-33396, (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-oxane)-16-ol, (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-ol, RefChem:5766, DTXCID301324626, 208-134-3, Diosgenine, MFCD00016887, DISOGENIN, (25R)-Spirost-5-en-3beta-ol, (2'R,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5',6a,8a,9-Tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol, (20R,25R)-Spirost-5-en-3beta-ol, NSC 33396, (25R)-14beta,17beta-spirost-5-en-3beta-ol, 3beta-Hydroxy-5-spirostene, SP 37, Spirost-5-en-3beta-ol, (25R)-, UNII-K49P2K8WLX, (25R)-5-Spirosten-3beta-ol, Spirost-5-en-3-ol, (3b,25R)-, nitrogen in, CCRIS 6803, Diosgenin CRS, 22alpha-Spirost-5-en-3beta-ol, (7S,8S,10S,13S,15S,18S,22S,3R,12R,14R,19R)-3,13,15,19-tetramethyl-11-oxaspiro[ 2H-3,4,5,6-tetrahydropyran-6,6'-pentacyclo[10.8.0.0<2,9>.0<4,8>.0<13,18>]icosa ne]-24-en-22-ol, YUV, EINECS 208-134-3, Diosgenin (Standard), BRN 0094582, Diosgenin, >=93%, DIOSGENIN [MI], 3A-Hydroxy-5-spirostene, 3?-Hydroxy-5-spirostene, DIOSGENIN [WHO-DD], SCHEMBL83359, 5-19-03-00030 (Beilstein Handbook Reference), (25R)-5-Spirosten-3b-ol, (25R)-5-Spirosten-3A-ol, CHEMBL412437, orb1304911, orb3140633, HY-N0177R, WLZ4700, HY-N0177, BDBM50617158, EBC-50097, LMST01080037, MSK159048, SBB058140, (3|_,25R)-spirost-5-en-3-ol, (3|A,25R)-Spirost-5-en-3-ol, AKOS015961083, Spirost-5-en-3-beta-ol, (25R)-, CS-5303, NCGC00386027-01, Spirost-5-en-3-ol, (3-beta,25R)-, AS-13640, ST097775, SY015253, NS00014256, S2291, (3.BETA.,25R)-SPIROST-5-EN-3-OL, C08898, M03858, EN300-7388351, F012718, Q1107734, BRD-K28690501-001-02-1, DIOSGENIN (CONSTITUENT OF FENUGREEK SEED) [DSC], Z1741961122, Diosgenin, European Pharmacopoeia (EP) Reference Standard, (25R)-5-Spirosten-3(1/4)?-ol ;  3(1/4)?-Hydroxy-5-spirostene, (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, (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-tetrahydropyran]-16-ol
Theoretical properties:
molecular_formula: C27H42O3
molecular_weight: 414.6 g/mol
exact_mass: 414.31339520 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 30
topological_polar_surface_area: 38.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Diosgenin is a sapogenin that is spirostan which is substituted by a hydroxy group at the 3beta position, contains a double bond at the 5-6 position, and has R- configuration at position 25. A natural product found in Dioscorea (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone. It has a role as an antiviral agent, a metabolite, an antineoplastic agent and an apoptosis inducer. It is a sapogenin, a 3beta-sterol, a hexacyclic triterpenoid and a spiroketal. It derives from a hydride of a spirostan.
chebi: A  sapogenin that is spirostan which is substituted by a hydroxy group at the 3β position, contains a double bond at the 5-6 position, and has <i>R</i>- configuration at position 25. A natural product found in <em>Dioscorea</em> (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone.
chembl: DISOGENIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Diosgenin, a phytosteroid spirostanol sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes  of saponins, extracted from the  tubers of Dioscorea wild yam species, such as the Kokoro. It is also present in smaller amounts in a number of other species.  The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products.