Compound: solasodine
SMILES: O1[C@@]2(NC[C@H](C)CC2)[C@@H](C)[C@H]3[C@@H]1C[C@H]4[C@H]5[C@@H]([C@@]6(C(C[C@@H](O)CC6)=CC5)C)CC[C@]34C
InChIKey: KWVISVAMQJWJSZ-VKROHFNGSA-N
Synonyms: solasodine, 126-17-0, Purapuridine, Solanidine-S, Solancarpidine, Solasodin, Solasod-5-en-3beta-ol, L40Y453Y96, Salasodine, Salasdine, CHEBI:9190, (3beta,22alpha,25R)-spirosol-5-en-3-ol, DTXSID101030558, NSC-178260, Spirosol-5-en-3-ol, (3beta,22alpha,25R)-, delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol, NSC-179187, (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'-piperidine]-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'-piperidine)-16-ol, RefChem:184222, DTXCID901515643, 204-774-2, 5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-piperidine)-16-ol, (22R,25R)-spirosol-5-en-3beta-ol, MFCD00037844, (4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-5',6a,8a,9-Tetramethyl-1,3,4,5,6,6a,6b,7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-piperidin]-4-ol, NSC178260, Solasod-5-en-3-beta-ol, Solancarpine, Spirosol-5-en-3-ol, (3.beta.,22.alpha.,25R)-, Solanearpidine, (-)-Solasodine, NSC 179187, Solasod-5-en-3.beta.-ol, SR-01000814832, Solancarpidine;, Purapuridine;, Purapuridine;Solancarpidine;Solasodin, Solanidine S;, NSC 178260, SOLASADINE, SOLASODINE [MI], Prestwick3_000663, SOLASODINE [WHO-DD], BSPBio_000725, MLS001164064, SCHEMBL456185, BPBio1_000799, CHEMBL518252, orb1303271, orb3139392, Solasodine - Bio-X trade mark, UNII-L40Y453Y96, HSDB 3538, MSK3003, KWVISVAMQJWJSZ-VKROHFNGSA-N, HMS2097E07, HMS2862C06, HY-N0068, EINECS 204-774-2, AKOS015969707, CS-1651, EBC-618395, OS73940, BRN 0094578, NCGC00179461-01, (25R)-22alpha-spirosol-5-en-3beta-ol, BS300158, SMR000539436, SY231499, AB00513879, NS00041398, 4-27-00-02000 (Beilstein Handbook Reference), Q740439, SR-01000814832-3, SR-01000814832-4, (2R,5'R)-5'-tetramethylspiro[[?]-2,2'-piperidine]ol, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-OL, (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-en-16-ol, (2'R,4S,5'R,6aR,6bS,8aS,8bR,9S,11aS,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,4,5,6,6a,6b,7,8,8a,8b,9,11a,12,12a,12b-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-piperidin]-4-ol, (2S,2'R,4aR,4bS,5'R,6aS,6bR,7S,9aS,10aS,10bS)-4a,5',6a,7-tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-piperidin]-2-ol
Theoretical properties:
molecular_formula: C27H43NO2
molecular_weight: 413.6 g/mol
exact_mass: 413.329379614 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 30
topological_polar_surface_area: 41.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: HEXAGONAL PLATES FROM METHANOL OR BY SUBLIMATION IN HIGH VACUUM
color: HEXAGONAL PLATES FROM METHANOL OR BY SUBLIMATION IN HIGH VACUUM
melting_point: 200-202 °C
solubility: FREELY SOL IN BENZENE, PYRIDINE, AND CHLOROFORM; MODERATELY SOL IN ALC, METHANOL, AND ACETONE; SLIGHTLY SOL IN WATER; PRACTICALLY INSOL IN ETHER
Descriptions:
pubchem: Solasodine is an oxaspiro compound and steroid alkaloid sapogenin with formula C27H43NO2 found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills. It has a role as an antispermatogenic agent, an antioxidant, an antiinfective agent, a central nervous system depressant, an antipyretic, a diuretic, an anticonvulsant, an antifungal agent, a cardiotonic drug, an immunomodulator, a teratogenic agent, an apoptosis inducer and a plant metabolite. It is a hemiaminal ether, a sapogenin, a steroid alkaloid, an azaspiro compound, an oxaspiro compound and an alkaloid antibiotic. It is a conjugate base of a solasodine(1+).
chebi: An oxaspiro compound and steroid alkaloid sapogenin with formula C<small><sub>27</sub></small>H<small><sub>43</sub></small>NO<small><sub>2</sub></small> found in the Solanum (nightshade) family. It is used as a precursor in the synthesis of complex steroidal compounds such as contraceptive pills.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg.
A 2013 literature survey found that various studies have indicated that solasodine may have diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and/or various other effects on central nervous system.