(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidin]-18-en-16-ol

• ChemBase ID: 129574
• Molecular Formular: C27H43NO2
• Molecular Mass: 413.63582
• Monoisotopic Mass: 413.32937962
• SMILES: O[C@@H]1CC2=CC[C@@H]3[C@H](CC[C@]4([C@H]3C[C@@H]3O[C@@]5(NC[C@H](C)CC5)[C@H]([C@H]43)C)C)[C@@]2(C)CC1
• Canonical SMILES: C[C@@H]1CC[C@@]2(NC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C
• InChI: InChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
• InChIKey: KWVISVAMQJWJSZ-VKROHFNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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,^8.0^1^3,^1^8]icosane-6,2'-piperidin]-18-en-16-ol
• IUPAC Traditional name: solasodine; (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,^8.0^1^3,^1^8]icosane-6,2'-piperidin]-18-en-16-ol
• Synonyms: Purapuridine; Solancarpidine; Solanearpidine; Solanidine-S; Solasodine; Solanidine S; Solancarpine; Solasodine

Database IDs

• CAS Number: 126-17-0
• EC Number: 204-774-2
• PubChem SID: 162223864
• PubChem CID: 442985
• CHEBI ID: CHEBI:565242
• CHEMBL: 514596
• Chemspider ID: 391288
• KEGG ID: C10822
• Wikipedia Title: Solasodine

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.4317597
• LogD (pH = 7.4): 2.4982748
• Log P: 4.6098776
• Molar Refractivity: 121.9468 cm^3
• Polarizability: 48.692955 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Safety Statements: R

Pharmacology Properties

• Mechanism of Action: Inhibitor of spermatogenesis and sperm motility; Inhibitor of testosterone release; Regulations of TNFR I and II expression

Product Information

• Description: Racemic
• Biological Source: Aglycone from many Solanum spp. and from Fritillaria camtschatcensis. Occurs free in Solanum trilobatum and Solanum dulcamara (Liliaceae, Solanaceae)
• Application(s): Antiandrogenic; Antiinflammatory; Antineoplastic agent; Antispermatogenic props.

REFERENCES

• Uhle, F.C., J.A.C.S., 1954, 76, 4245, (synth, struct)
• Budzikiewicz, H., Tetrahedron, 1964, 2267, (ms)
• Schreiber, K. et al., Tetrahedron, 1964, 20, 1939; 1966, 22, 3591, (struct, synth)
• Boll, P.M. et al., Acta Chem. Scand., 1965, 19, 1365, (pmr, config)
• Wolters, B., Planta Med., 1966, 14, 392-401, (activity)
• Puroshathaman, K.K. et al., Aust. J. Chem., 1969, 22, 2153
• Kessar, S.V. et al., Tetrahedron, 1971, 27, 2153-2159, (synth)
• Weston, R.J. et al., Aust. J. Chem., 1977, 30, 917, (cmr)
• Bird, G.J. et al., Aust. J. Chem., 1979, 32, 783, (cmr)
• Ripperger, H. et al., Alkaloids (N.Y.), 1981, 19, 81, (rev)
• Ripperger, H. et al., Phytochemistry, 1997, 46, 1279-1282, (Solasuaveoline, Isosolasuaveoline)
• Hu, K. et al., Planta Med., 1999, 65, 35-38, (isol, activity)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, POJ000