Compound: PTAQUILOSIDE
SMILES: O=C1[C@@H]2[C@](O)(C3(C(C)=C[C@]2(O[C@@H]4O[C@@H]([C@@H](O)[C@@H]([C@H]4O)O)CO)C[C@H]1C)CC3)C
InChIKey: GPHSJPVUEZFIDE-YVPLJZHISA-N
Synonyms: PTAQUILOSIDE, 87625-62-5, Braxin C, DTXSID20892005, F0MN9S5699, (2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one, (2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyspiro(3,7a-dihydro-2H-indene-6,1'-cyclopropane)-1-one, Spiro(cyclopropane-1,5'-(5H)inden)-3'(2'H)-one, 7'a-(beta-D-glucopyranosyloxy)-1',3'a,4',7'a-tetrahydro-4'-hydroxy-2',4',6'-trimethyl-, RefChem:870295, DTXCID801035935, C20H30O8, UNII-F0MN9S5699, CCRIS 1591, Ptaquiloside (Braxin C), PTAQUILOSIDE [MI], PTAQUILOSIDE [IARC], orb1681843, SCHEMBL3993356, GLXC-19158, HY-N7882, AKOS040762234, FP159309, CS-0138739, NS00066985, (2'R,3'aR,4'S,7'aR)-4'-Hydroxy-2',4',6'-trimethyl-3'-oxo-2',3',3'a,4'-tetrahydrospiro[cyclopropane-1,5'-inden]-7'a(1'H)-yl beta-D-glucopyranoside, (2R,3AR,4S,7AR)-7A-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,3A,4,7A-TETRAHYDRO-4-HYDROXY-2,4,6-TRIMETHYLSPIRO(CYCLOPROPANE-1,5-(5H)INDEN)-3(2H)-ONE, (2R,3aR,7S,7aR)-7-hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-spiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one, piro(cyclopropane-1,5'-(5H)indan)-3'(2'H)-one, 7'a-(beta-D-glucopyranosyloxy)-1',3'a,4',7'a-tetrahydro-4'-hydroxy-2',4',6'-trimethyl-, (2'R-(2'alpha,3'aalpha,4'beta.7'aalpha))-, Spiro(cyclopropane-1,5'-(5H)indan)-3'(2'H)-one, 7'a-(beta-D-glucopyranosyloxy)-1',3'a,4',7'a-tetrahydro-4'-hydroxy-2',4',6'-trimethyl-, (2'R,3'aR,4'S,7'aR)-, Spiro(cyclopropane-1,5'-(5H)inden)-3'(2'H)-one, 1',3'-alpha,4',7'-alpha-tetrahydro-7'-alpha-(beta-D-glucopyranosyloxy)-4'-hydroxy-2',4',6'-trimethyl-, SPIRO(CYCLOPROPANE-1,5'-(5H)INDEN)-3'(2'H)-ONE, 7'A-(.BETA.-D-GLUCOPYRANOSYLOXY)-1',3'A,4',7'A-TETRAHYDRO-4'-HYDROXY-2',4',6'-TRIMETHYL-, (2'R,3'AR,4'S,7'AR)-
Theoretical properties:
molecular_formula: C20H30O8
molecular_weight: 398.4 g/mol
exact_mass: 398.19406791 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 3
heavy_atom_count: 28
topological_polar_surface_area: 137 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: Ptaquiloside is a norsesquiterpene glucoside produced by bracken ferns (majorly Pteridium aquilinum) during metabolism. It is identified to be the main carcinogen of the ferns and to be responsible for their biological effects, such as haemorrhagic disease and bright blindness in livestock and oesophageal, gastric cancer in humans. Ptaquiloside has an unstable chemical structure and acts as a DNA alkylating agent under physiological conditions. It was first isolated and characterized by Yamada and co-workers in 1983.
The pure form ptaquiloside is a colorless amorphous compound. It is readily soluble in water and fairly soluble in ethyl acetate. Except in the plants, ptaquiloside has been detected in the milk and meat of affected livestock, as well as in the underground water and dry soil around bracken fern vegetation. The prevalence of ptaquiloside in daily sources along with its carcinogenic effects make it an increasing biological hazard in modern days.