Compound: Strictosidine
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]1C[C@@H]3NCCc4c3[nH]c5ccccc45)C=C
InChIKey: XBAMJZTXGWPTRM-NTXHKPOFSA-N
Synonyms: Strictosidine, 20824-29-7, Isovincoside, 45T874R5N4, methyl (2S,3R,4S)-3-ethenyl-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate, DTXSID40943068, methyl (2S,3R,4S)-3-ethenyl-4-(((1S)-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indol-1-yl)methyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3,4-dihydro-2H-pyran-5-carboxylate, RefChem:186023, DTXCID801371446, (2S-(2 alpha,3 beta,4 beta(R*)))-3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-((2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indol-1-yl) methyl)-2H-pyran-5-carboxylic acid, methyl ester, 3alpha(S)-strictosidine, 3-alpha(S)-Strictosidine, 3-Isovincoside, (2S,3R,4S)-Methyl 4-(((S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)methyl)-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, methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-ylmethyl]-3,4-dihydro-2H-pyran-5-carboxylate, STRICTOSIDIN, (-)-Strictosidine, CHEMBL402211, orb1681635, SCHEMBL8322946, SCHEMBL29456742, UNII-45T874R5N4, CHEBI:17559, AKOS040762379, FS-7040, FS71929, DA-78063, HY-124165, CS-0084513, C03470, Q2356148, (2S-(2alpha,3beta,4beta(R*)))-3-Ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-((2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indol-1-yl) methyl)-2H-pyran-5-carboxylic acid, methyl ester, 2H-Pyran-5-carboxylic acid, 3-ethenyl-2-(beta-D-glucopyranosyloxy)-3,4-dihydro-4-((2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indol-1-yl)methyl)-, methyl ester, (2S-(2alpha,3beta,4beta(R*)))-, Methyl (2S,3R,4S)-3-ethenyl-2-(beta-D-glucopyranosyloxy)-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl}-3,4-dihydro-2H-pyran-5-carboxylate, methyl (2S,3R,4S)-4-(((S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)methyl)-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, methyl (2S,3R,4S)-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-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 (4S,5R,6S)-5-ethenyl-4-{[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl}-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate
Theoretical properties:
molecular_formula: C27H34N2O9
molecular_weight: 530.6 g/mol
exact_mass: 530.22643067 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 8
heavy_atom_count: 38
topological_polar_surface_area: 163 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 3alpha(S)-strictosidine is a beta-D-glucoside, a methyl ester, an alkaloid ester and an indole alkaloid. It is a conjugate base of a 3alpha(S)-strictosidinium(1+).
chembl: STRICTOSIDINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase.  Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids.  Strictosidine is an intermediate in the biosynthesis of numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine, vincristine and mitragynine.
Biosynthetic pathways help to define the subgroups of strictosidine derivatives.