chlorocardicin   Click here for help

GtoPdb Ligand ID: 11044

Comment: Chlorocardicin is a monocyclic β-lactam produced by Streptomyces sp. [1-2]. It is structurally related to nocardicin A, and has a similar activity profile.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 12
Topological polar surface area 212.08
Molecular weight 534.12
XLogP -0.66
No. Lipinski's rules broken 2
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Canonical SMILES O/N=C(\c1ccc(cc1)OCC[C@H](C(=O)O)N)/C(=O)N[C@H]1CN(C1=O)[C@H](c1ccc(c(c1)Cl)O)C(=O)O
Isomeric SMILES O/N=C(\c1ccc(cc1)OCC[C@H](C(=O)O)N)/C(=O)N[C@H]1CN(C1=O)[C@H](c1ccc(c(c1)Cl)O)C(=O)O
InChI InChI=1S/C23H23ClN4O9/c24-14-9-12(3-6-17(14)29)19(23(34)35)28-10-16(21(28)31)26-20(30)18(27-36)11-1-4-13(5-2-11)37-8-7-15(25)22(32)33/h1-6,9,15-16,19,29,36H,7-8,10,25H2,(H,26,30)(H,32,33)(H,34,35)/b27-18+/t15-,16+,19-/m1/s1
1. Chan JA, Shultis EA, Dingerdissen JJ, DeBrosse CW, Roberts GD, Snader KM. (1985)
Chlorocardicin, a monocyclic beta-lactam from a Streptomyces sp. II. Isolation, physico-chemical properties and structure determination.
J Antibiot, 38 (2): 139-44. [PMID:3838979]
2. Nisbet LJ, Mehta RJ, Oh Y, Pan CH, Phelen CG, Polansky MJ, Shearer MC, Giovenella AJ, Grappel SF. (1985)
Chlorocardicin, a monocyclic beta-lactam from a Streptomyces sp. I. Discovery, production and biological activities.
J Antibiot, 38 (2): 133-8. [PMID:3922933]