Compound: Solamargine
SMILES: O1[C@@H](O[C@@H]2CC3=CC[C@H]4[C@H]5[C@]([C@H]6[C@@H]([C@]7(NC[C@H](C)CC7)O[C@H]6C5)C)(C)CC[C@@H]4[C@@]3(C)CC2)[C@H](O[C@@H]8O[C@H]([C@H](O)[C@H]([C@H]8O)O)C)[C@@H](O)[C@@H]([C@H]1CO)O[C@@H]9O[C@H]([C@H](O)[C@H]([C@H]9O)O)C
InChIKey: MBWUSSKCCUMJHO-ZGXDEBHDSA-N
Synonyms: Solamargine, 20311-51-7, 8KG991E7BN, DTXSID00942456, NSC-407810, (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(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-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol, (2S,3R,4R,5R,6S)-2-((2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-((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-yl)oxy-5-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol, RefChem:184184, DTXCID001514400, Solamargin, a-Solamargine, UNII-8KG991E7BN, MFCD30207844, NSC 407810, |A-Solanigrine, beta-D-Glucopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-, AC1L2K61, NSC407810, (3ss,22a,25R)-Spirosol-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1?2)-O-[6-deoxy-a-L-mannopyranosyl-(1?4)]-ss-D-glucopyranoside; NSC 407810; Solamargin; a-Solamargine; d-Solanigrine;, Solasodine-L-rhamnosido-D-glucoside, Solanigrine, (-)-, DELTA-SOLANIGRINE, (-)-SOLAMARGINE, CHEBI:9185, CHEMBL443114, orb1303274, orb3139394, SCHEMBL27829541, HY-N0069, MSK163965, s9145, AKOS030526705, CCG-270542, DB12700, EBC-615887, OS65545, AS-75093, DA-57990, NS00073646, Q3489126, (25R)-22alpha-Spirosol-5-en-3beta-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-[6-deoxy-alpha-L-mannopyranosyl-(1->4)]-beta-D-glucopyranoside, (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(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-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol, (2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(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-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol, (3b,22a,25R)-Spirosol-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1?2)-O-[6-deoxy-a-L-mannopyranosyl -(1?4)]-b-D-glucopyranoside, (3beta,22alpha,25R)-Spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside, b-D-Glucopyranoside, (3b,22a,25R)-spirosol-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1(R)2)-O-[6-deoxy-a-L-mannopyranosyl-(1(R)4)]-, beta-D-Glucopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-
Theoretical properties:
molecular_formula: C45H73NO15
molecular_weight: 868.1 g/mol
exact_mass: 867.49802062 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 9
hydrogen_bond_acceptor_count: 16
rotatable_bond_count: 7
heavy_atom_count: 61
topological_polar_surface_area: 238 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Solamargine is a steroid, an azaspiro compound and an oxaspiro compound.
chembl: SOLAMARGINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Solamargine is a cytotoxic chemical compound that occurs in plants of the family Solanaceae, such as potatoes, tomatoes, and eggplants. It has been also isolated from Solanum nigrum fungal endophyte Aspergillus flavus. It is a glycoalkaloid derived from the steroidal alkaloid solasodine.
Solamargine was one component of the unsuccessful experimental cancer drug candidate Coramsine.