Molecule ID: 102453304

IUPAC Name: N-[(2S,3S,4R,5S,6R)-4,5-dihydroxy-6-[4-[(E)-2-isocyanoethenyl]phenoxy]-2-methyloxan-3-yl]acetamide

Description: The molecule is an isocyanide that is the 4-acetamido-4,6-dideoxy-beta-L-galactopyranoside of p-[(E)-2-isocyanovinyl]phenol. Produced by the gram-negative insect pathogens, Xenorhabdus nematophila and Photorhabdus luminescens, it is a potent nanomolar-level inhibitor of phenoloxidase, a key component of the insect's innate immune system. It has a role as a bacterial metabolite and an EC 1.14.18.1 (tyrosinase) inhibitor. It is an isocyanide, a member of acetamides and an olefinic compound.

SMILES: [C-]#[N+]/C=C/c1ccc(O[C@H]2O[C@@H](C)[C@@H](N=C(C)O)[C@@H](O)[C@@H]2O)cc1

SELFIES: [C-1][#N+1][/C][=C][/C][=C][C][=C][Branch2][Ring1][=Branch2][O][C@H1][O][C@@H1][Branch1][C][C][C@@H1][Branch1][#Branch1][N][=C][Branch1][C][C][O][C@@H1][Branch1][C][O][C@@H1][Ring1][N][O][C][=C][Ring2][Ring1][Ring2]

InChI: InChI=1S/C17H20N2O5/c1-10-14(19-11(2)20)15(21)16(22)17(23-10)24-13-6-4-12(5-7-13)8-9-18-3/h4-10,14-17,21-22H,1-2H3,(H,19,20)/b9-8+/t10-,14+,15+,16-,17+/m0/s1

Molecular Properties:
- Polar Surface Area: 92.4 Ų
- LogP: 0.4