Compound: alpha-Chaconine
SMILES: O1[C@@H](O[C@@H]2CC3=CC[C@H]4[C@H]5[C@]([C@H]6[C@@H]([C@H]7CC[C@@H](CN7[C@H]6C5)C)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: TYNQWWGVEGFKRU-AJDPQWBVSA-N
Synonyms: alpha-Chaconine, 20562-03-2, 5QOL0LIM81, DTXSID501016601, (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-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,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-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:111118, DTXCID301474794, (2S,3R,4R,5R,6S)-2-((2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-(((1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl)oxy-6-methyloxane-3,4,5-triol, 2-((4-hydroxy-2-(hydroxymethyl)-6-((10,14,16,20-tetramethyl-22-azahexacyclo(12.10.0.02,11.05,10.015,23.017,22)tetracos-4-en-7-yl)oxy)-5-((3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)oxan-3-yl)oxy)-6-methyloxane-3,4,5-triol, 633-788-5, Conine, Chaconine, a-Chaconine, |A-Chaconine, alpha-?Chaconine, MFCD09039102, .alpha.-Chaconine, UNII-5QOL0LIM81, CCRIS 6509, alpha -Chaconine, TYNQWWGVEGFKRU-AJDPQWBVSA-N, |_-Chaconine, ??-?Chaconine, BRN 0077396, |A-?Chaconine (Standard), 4-21-00-01401 (Beilstein Handbook Reference), orb1684776, orb3140196, .ALPHA.-CHACONINE [MI], SCHEMBL29389898, CHEBI:10219, MSK10421, AKOS040760264, HY-129113R, OC29325, DA-50353, MS-31576, HY-129113, CS-0103657, NS00094322, G13546, Q2947331, (2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-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, (3b)-Solanid-5-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1-2)-O-(6-deoxy-a-L-mannopyranosyl-(1-4))-b-D-glucopyranoside, .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.)-SOLANID-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-, beta-D-Glucopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-, Solanid-5-en-3beta-yl 6-deoxy-alpha-L-mannopyranosyl-(1->2)-[6-deoxy-alpha-L-mannopyranosyl-(1->4)]-beta-D-glucopyranoside
Theoretical properties:
molecular_formula: C45H73NO14
molecular_weight: 852.1 g/mol
exact_mass: 851.50310600 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 7
heavy_atom_count: 60
topological_polar_surface_area: 220 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Alpha-Chaconine is a glycoalkaloid and a steroid saponin.
wikipedia: α-Chaconine is a steroidal glycoalkaloid that occurs in plants of the family Solanaceae. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste. Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties. It belongs to the chemical family of saponins. Since it causes physiological effects on individual organism, chaconine is considered to be a defensive allelochemical. Solanine, a related substance also found in potatoes, has similar properties.