Molecule ID: 129039

IUPAC Name: (2S)-2-[[(2R)-6-amino-2-[(2,3-dihydroxybenzoyl)amino]hexanoyl]amino]-3-hydroxypropanoic acid

Description: The molecule is a catechol-type siderophore with a structure of D-lysyl-L-serine substituted on N(2) of the lysyl residue by a 2,3-dihydroxybenzoyl group. It is produced by the Gram-negative bacillus Dickeya dadantii (previously known as Erwinia chrysanthem). Only the catecholate hydroxyl groups participate in metal coordination, so chrysobactin cannot provide full 1:1 coordination of Fe(III); at neutral pH and concentrations of about 0.1 mM, ferric chrysobactin exists as a mixture of bis and tris complexes. It has a role as a siderophore and a bacterial metabolite. It is a member of catechols, a dipeptide, a monocarboxylic acid, a primary alcohol and a primary amino compound.

SMILES: NCCCC[C@@H](N=C(O)c1cccc(O)c1O)C(O)=N[C@@H](CO)C(=O)O

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

InChI: InChI=1S/C16H23N3O7/c17-7-2-1-5-10(15(24)19-11(8-20)16(25)26)18-14(23)9-4-3-6-12(21)13(9)22/h3-4,6,10-11,20-22H,1-2,5,7-8,17H2,(H,18,23)(H,19,24)(H,25,26)/t10-,11+/m1/s1

Molecular Properties:
- Polar Surface Area: 182.0 Ų
- LogP: -2.8