Molecule ID: 136661909

IUPAC Name: [(4S,5R,6S,8S,10R)-10-[(2,4-dioxo-1H-pyrimidin-6-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.04,12]dodec-1(11)-en-6-yl] hydrogen sulfate

Description: The molecule is a triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer). A non-toxic analogue of the cyanotoxins cylindrospermopsin and 7-epi-cylindrospermopsin (the latter two have a hydroxy group attached to the carbon adjacent to the uracil ring), it is produced by several species of freshwater cyanobacteria, such as Cylindrospermopsis raciborskii. It has a role as a protein synthesis inhibitor. It is an alkaloid, a member of cylindrospermopsins, an organic sulfate, a pyrimidone and a triazaacenaphthylene. It is a tautomer of a deoxycylindrospermopsin zwitterion.

SMILES: C[C@H]1[C@@H](OS(=O)(=O)O)C[C@@H]2C[C@H](Cc3cc(O)nc(O)n3)NC3=NC[C@H]1N32

SELFIES: [C][C@H1][C@@H1][Branch1][#Branch2][O][S][=Branch1][C][=O][=Branch1][C][=O][O][C][C@@H1][C][C@H1][Branch1][S][C][C][=C][C][Branch1][C][O][=N][C][Branch1][C][O][=N][Ring1][Branch2][N][C][=N][C][C@H1][Ring2][Ring1][=Branch2][N][Ring1][Branch1][Ring2][Ring1][C]

InChI: InChI=1S/C15H21N5O6S/c1-7-11-6-16-14-17-8(2-9-4-13(21)19-15(22)18-9)3-10(20(11)14)5-12(7)26-27(23,24)25/h4,7-8,10-12H,2-3,5-6H2,1H3,(H,16,17)(H,23,24,25)(H2,18,19,21,22)/t7-,8+,10+,11-,12+/m1/s1

Molecular Properties:
- Polar Surface Area: 158.0 Ų
- LogP: -1.5