Compound: Amarogentin
SMILES: O=C1OCC[C@@H]2C1=CO[C@@H](O[C@@H]3O[C@@H]([C@@H](O)[C@@H]([C@H]3OC(=O)c4c(O)cc(O)cc4-c5cc(O)ccc5)O)CO)[C@@H]2C=C
InChIKey: DBOVHQOUSDWAPQ-WTONXPSSSA-N
Synonyms: Amarogentin, 21018-84-8, 5L82GT5I0W, DTXSID501029787, [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate, CHEBI:2622, (4aR)-5t-ethenyl-6c-[O(2)-(3,5,3'-trihydroxybiphenyl-2-ylcarbonyl)-beta-D-glucopyranosyloxy]-4,4ar,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one, ((2S,3R,4S,5S,6R)-2-(((3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano(3,4-c)pyran-3-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl) 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate, (4aR)-5t-ethenyl-6c-(O(2)-(3,5,3'-trihydroxybiphenyl-2-ylcarbonyl)-beta-D-glucopyranosyloxy)-4,4ar,5,6-tetrahydro-3H-pyrano(3,4-c)pyran-1-one, RefChem:111835, DTXCID401514995, sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester, (2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(((3S,4R,4aS)-8-oxo-4-vinyl-3,4,4a,5,6,8-hexahydropyrano[3,4-c]pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl 3,3',5-trihydroxy-[1,1'-biphenyl]-2-carboxylate, (4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl- 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranoside, DBOVHQOUSDWAPQ-WTONXPSSSA-N, Amarogentin (Standard), AMAROGENTIN [MI], C09767, UNII-5L82GT5I0W, SCHEMBL1031187, GTPL12459, HY-N2447R, HY-N2447, C29H30O13, s1273, AKOS015896722, EBC-618508, (2S,3R,4S,5S,6R)-2-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 3,3',5-trihydroxy-[1,1'-biphenyl]-2-carboxylate, DA-70749, FA146492, CS-0022673, NS00120927, Q3613679, 2-(4aS-(4aalpha,5beta,6alpha))-3,3',5-Trihydroxy-(1,1'-biphenyl)-2-carboxylate, (1,1'-Biphenyl)-2-carboxylic acid, 3,3',5-trihydroxy-, 2-ester with 5-ethenyl-6-(beta-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano(3,4-c)pyran-1-one, (4aS-(4aalpha,5beta,6alpha))-, [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-8-oxo-4-vinyl-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate, 1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-4,4a,5,6-tetrahydro-6-((2-O-((3,3',5-trihydroxy(1,1'-biphenyl)-2-yl)carbonyl)-beta-D-glucopyranosyl)oxy)-, (4aS,5R,6S)-
Theoretical properties:
molecular_formula: C29H30O13
molecular_weight: 586.5 g/mol
exact_mass: 586.16864101 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 13
rotatable_bond_count: 8
heavy_atom_count: 42
topological_polar_surface_area: 202 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Amarogentin is a secoiridoid glycoside that consists of (4aS,5R,6R)-5-ethenyl-6-hydroxy-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one having a 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranosyl group attached at position 6 via a glycosidic linkage. It has a role as a metabolite and an EC 5.99.1.2 (DNA topoisomerase) inhibitor. It is a secoiridoid glycoside and a monosaccharide derivative.
chebi: A secoiridoid glycoside that consists of (4a<i>S</i>,5<i>R</i>,6<i>R</i>)-5-ethenyl-6-hydroxy-4,4a,5,6-tetrahydro-1<em>H</em>,3<em>H</em>-pyrano[3,4-<em>c</em>]pyran-1-one having a  2-<em>O</em>-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-β-<small>D</small>-glucopyranosyl group attached at position 6 via a glycosidic linkage.
wikipedia: Amarogentin is a chemical compound found in gentian 7 organisms, including: Swertia chirata (d),,,,, Gentiana lutea,,,, Gentiana purpurea, Gentianella nitida,, Swertia japonica,,,,,

Gentian root has a long history of use as a herbal bitter in the treatment of digestive disorders and is an ingredient of many proprietary medicines. The bitter principles of gentian root are secoiridoid glycosides amarogentin and gentiopicrin. The former is one of the most bitter natural compounds known and is used as a scientific basis for measuring bitterness. In humans, it activates the bitter taste receptor TAS2R50. The biphenylcarboxylic acid moiety is biosynthesized by a polyketide-type pathway, with three units of acetyl-CoA and one unit of 3-hydroxybenzoyl-CoA, this being formed from an early shikimate pathway intermediate and not via cinnamic or benzoic acid.
It also shows an antileishmanial activity in animal models being an inhibitor of topoisomerase I.