Compound: Digitoxigenin
SMILES: O=C1OCC(=C1)[C@@H]2[C@@]3([C@@](O)([C@H]4[C@@H]([C@@]5([C@@H](C[C@@H](O)CC5)CC4)C)CC3)CC2)C
InChIKey: XZTUSOXSLKTKJQ-CESUGQOBSA-N
Synonyms: Digitoxigenin, 143-62-4, Cerberigenin, Echujetin, Evonogenin, Thevetigenin, S63WOD4VOL, 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one, 3beta,14-Dihydroxy-5beta-card-20(22)-enolide, NSC-407806, delta20:22-3,14,21-Trihydroxynorcholenic acid lactone, CHEBI:42219, DTXSID80162276, 3-beta,14beta-dihydroxy-5-beta-card-20(22)-enolide, Card-20(22)-enolide, 3,14-dihydroxy-, (3beta,5beta)-, 3-((3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-2H-furan-5-one, RefChem:388929, DTXCID6084767, 205-603-4, Digitoxigenine, MLS002153810, MFCD00003687, NSC 407806, SMR001233182, DTX, 3.beta.,14-Dihydroxy-5.beta.-card-20(22)-enolide, .delta.20:22-3,14,21-Trihydroxynorcholenic acid lactone, Card-20(22)-enolide, 3,14-dihydroxy-, (3.beta.,5.beta.)-, 3b,14-Dihydroxy-5b-card-20(22)-enolide, MLS002701726, UNII-S63WOD4VOL, (+)-DIGITOXIGENIN, Cerberigenin;, Thevetigenin;, NSC407806, 1lnm, 4-(3,14-DIHYDROXY-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-17-YL)-5H-FURAN-2-ONE, Digitoxigenin; (+)-Digitoxigenin; NSC 407806; Card-20(22)-enolide, 3,14-dihydroxy-, (3beta,5beta)-; 5beta-Card-20(22)-enolide, 3beta,14-dihydroxy- (6CI,7CI,8CI); Delta20:22-3,14,21-Trihydroxynorcholenic acid lactone, Prestwick_169, EINECS 205-603-4, BRN 0095448, 3-beta,14-Dioxy-carden-(20:22)-olid, 3-beta,14-Dioxy-digen-(20:22)-olid, Cardogenen-(20:22)-diol-(3-beta,14), Prestwick0_000436, Prestwick1_000436, Prestwick2_000436, Prestwick3_000436, DIGITOXIGENIN [MI], CHEMBL1453, 3-beta,14-Dioxy-digen-(20:22)-olid [German], SCHEMBL61224, BSPBio_000452, 3-beta,14-Dihydroxy-5-beta-card-20(22)-enolide, 3-beta,14-Dioxy-carden-(20:22)-olid [German], 5-18-03-00348 (Beilstein Handbook Reference), Cardogenen-(20:22)-diol-(3-beta,14) [German], SPBio_002391, BPBio1_000498, BDBM66977, cid_4369270, 3-beta,14-Dihydroxy-5-beta,14-beta-card-20(22)-enolide, Card-20(22)-enolide, 3,14-dihydroxy-, (3-beta,5-beta)-, delta-sup(20:22)-3,14,21-Trihydroxynorcholenic acid lactone, delta-sup(20:22)-3,14,21-Trihydroxynorcholenicacid lactone, HMS1569G14, HMS2096G14, HMS2231J22, HMS3713G14, LMST01120001, AKOS015915862, CCG-220436, DB04177, FD11670, 5b,20(22)-Cardenolide-3?,14-diol, NCGC00179555-01, 4-((3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one, AC-38163, 3-.beta.,14-Dioxy-digen-(20:22)-olid, 3b,14-Dihydroxy-5b,20(22)-cardenolide,, 3b,14b-dihydroxy-5b-carda-20(22)-enolid, D0541, NS00009205, Cardogenen-(20:22)-diol-(3-.beta.,14), 5.beta.-Card-20(22)-enolide,14-dihydroxy-, A12049, 3-BETA, 14-BETA-CARD-20(22)-ENOLIDE, F801786, Q411469, SR-01000841188, 5beta-Card-20(22)-enolide, 3beta,14-dihydroxy-, SR-01000841188-2, 3,14,21-Trihydroxy-20(22)-norcholenic acid lactone, BRD-K18518344-001-03-5, BRD-K18518344-001-15-9, .delta.20:22-3,21-Trihydroxynorcholenic acid lactone, 5.beta.-Card-20(22)-enolide, 3.beta.,14-dihydroxy, 5.beta.-Card-20(22)-enolide, 3.beta.,14-dihydroxy-, WLN: L E5 B666TJ A1 E1 F- DT5OV CUTJ IQ OQ, (3alpha,5beta,8alpha)-3,14-dihydroxycard-20(22)-enolide, 5-beta-CARD-20(22)-ENOLIDE, 3-beta,14-DIHYDROXY-, .delta.-sup(20:22)-3,21-Trihydroxynorcholenic acid lactone, 3,14-Dihydroxycard-20(22)-enolide, (3.beta.,5.beta.)- #, Card-20(22)-enolide,14-dihydroxy-, (3.beta.,5.beta.)-, .DELTA.-sup(20:22)-3,14,21-Trihydroxynorcholenicacid lactone, 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,14-bis(oxidanyl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Theoretical properties:
molecular_formula: C23H34O4
molecular_weight: 374.5 g/mol
exact_mass: 374.24570956 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 27
topological_polar_surface_area: 66.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Digitoxigenin is a 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22). It is a 3beta-hydroxy steroid and a 14beta-hydroxy steroid. It derives from a hydride of a 5beta-cardanolide.
chebi: A 5β-cardenolide that is 5β-cardanolide with hydroxy substituents at the 3β- and 14β-positions and double bond unsaturation at C(20)-C(22).
chembl: DIGITOXIGENIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Digitoxigenin, a cardenolide, is the aglycone of digitoxin.
Digitoxigenin can be used to prepare actodigin.
In Lednicer's book on steroids, it is made from deoxycholic acid.