Molecule ID: 132016

IUPAC Name: (3R,4S,7R,11S)-4-[(2R,3R,4R,5S,6S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-11-ethyl-3,7-dimethyl-azacyclotetradecan-2-one

Description: The molecule is a lactam that is 4-hydroxyazacyclotetradecan-2-one substituted by an ethyl group at position 11, methyl groups at position 3 and 7 and a 3-amino-3,6-dideoxy-alpha-L-talopyranosyl moiety at position 4 via a glycosyl linkage (the 3R,4S,7R,11S stereoisomer). It is isolated from the fermentation broth of an unidentified actinomycete species and exhibits potent inhibitory activity against influenza A virus. It has a role as an antimicrobial agent, an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor and a metabolite. It is an aminoglycoside, a lactam and a macrocycle.

SMILES: CC[C@@H]1CCCN=C(O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@@H](O)[C@@H](N)[C@H]2O)CC[C@H](C)CCC1

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

InChI: InChI=1S/C23H44N2O5/c1-5-17-9-6-8-14(2)11-12-18(15(3)22(28)25-13-7-10-17)30-23-21(27)19(24)20(26)16(4)29-23/h14-21,23,26-27H,5-13,24H2,1-4H3,(H,25,28)/t14-,15-,16+,17+,18+,19-,20-,21-,23+/m1/s1

Molecular Properties:
- Polar Surface Area: 114.0 Ų
- LogP: 3.0