Chaconine

Chaconine
	3D model of chaconine using MolView
Names
	IUPAC name Solanid-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside
	Systematic IUPAC name (2S,2′S,3R,3′R,4R,4′R,5R,5′R,6S,6′S)-2,2′-{[(2R,3S,4S,5R,6R)-4-Hydroxy-2-(hydroxymethyl)-6-{[(2S,4aR,4bS,6aS,6bR,7S,7aR,10S,12aS,13aS,13bS)-4a,6a,7,10-tetramethyl-1,3,4,4a,4b,5,6,6a,6b,7,7a,8,9,10,11,12a,13,13a,13b,14-icosahydro-2H-naphtho[2′,1′:4,5]indeno[1,2-b]indolizin-2-yl]oxy}oxane-3,5-diyl]bis(oxy)}bis(6-methyloxane-3,4,5-triol)
	Other names α-Chaconine, Chaconine
Identifiers
CAS Number	20562-03-2 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	77396
ChEBI	CHEBI:10219;
ChEMBL	ChEMBL2288884;
ChemSpider	391274 ;
ECHA InfoCard	100.161.828
KEGG	C10796;
PubChem CID	442971;
UNII	5QOL0LIM81 ;
CompTox Dashboard (EPA)	DTXSID501016601 ;
	InChI InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33-,34+,35+,36+,37+,38-,39+,40+,41-,42-,43+,44-,45-/m0/s1 Key: TYNQWWGVEGFKRU-AJDPQWBVSA-N ; InChI=1/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33-,34+,35+,36+,37+,38-,39+,40+,41-,42-,43+,44-,45-/m0/s1 Key: TYNQWWGVEGFKRU-AJDPQWBVBS;
	SMILES O([C@H]8[C@H](O[C@@H]4C/C3=C/C[C@H]2[C@@H]5C[C@@H]1N6[C@@H]([C@@H](C)[C@@H]1[C@@]5(C)CC[C@@H]2[C@@]3(C)CC4)CC[C@H](C)C6)O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@@H]8O)[C@@H]9O[C@H]([C@H](O)[C@@H](O)[C@H]9O)C; C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@@H]([C@@H](O9)C)O)O)O)C)C)C;
Properties
Chemical formula	C45H73NO14
Molar mass	852.072 g·mol−1
Melting point	243 °C (469 °F; 516 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H361
Precautionary statements	P203, P280, P318, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.