Compound: Secologanin
SMILES: O=C(OC)C1=CO[C@@H](O[C@@H]2O[C@@H]([C@@H](O)[C@@H]([C@H]2O)O)CO)[C@@H]([C@@H]1CC=O)C=C
InChIKey: CSKKDSFETGLMSB-NRZPKYKESA-N
Synonyms: Secologanin, 19351-63-4, (-)-Secologanin, NK7B26K93T, methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate, CHEBI:18002, NSC-640525, 3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester, methyl (2S,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3,4-dihydro-2H-pyran-5-carboxylate, RefChem:931561, loniceroside, methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate, Methyl (2S,3R,4S)-4-(2-oxoethyl)-2-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate, NSC 640525, Loniceroside (iridoid), Secologanin (Standard), UNII-NK7B26K93T, SCHEMBL431171, Secologanin, analytical standard, CHEMBL1235867, DTXSID30941033, MFCD16661163, AKOS040753996, FS65469, HY-125598R, LMPR0102070002, NCGC00384550-01, METHYL (2S,3R,4S)-2-(BETA-D-GLUCOPYRANOSYLOXY)-4-(2-OXOETHYL)-3-VINYL-3,4-DIHYDRO-2H-PYRAN-5-CARBOXYLATE, MS-26429, HY-125598, CS-0092439, NS00074296, C01852, G13893, Q1531155, F19BE380-C97E-46CC-89C6-F6BCAFC793EC, 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-, methyl ester, (2S,3R,4S)-, methyl (2S,3R,4S)-4-(2-oxoethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate, methyl (2S,3R,4S)-4-(formylmethyl)-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate, NCGC00384550-01_C17H24O10_Methyl (2S,3R,4S)-2-(beta-D-glucopyranosyloxy)-4-(2-oxoethyl)-3-vinyl-3,4-dihydro-2H-pyran-5-carboxylate
Theoretical properties:
molecular_formula: C17H24O10
molecular_weight: 388.4 g/mol
exact_mass: 388.13694696 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 8
heavy_atom_count: 27
topological_polar_surface_area: 152 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (-)-secologanin is an iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer). It has a role as a plant metabolite. It is an aldehyde, a beta-D-glucoside, a methyl ester, a member of pyrans, a secoiridoid glycoside and an enoate ester.
chebi: An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(β-<small>D</small>-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2<i>S</i>,3<i>R</i>,4<i>S</i> stereoisomer).
chembl: SECOLOGANIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively.