chlorocardicin   

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
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
SMILES / InChI / InChIKey
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
InChI Key UMDAIHWMUXNVSB-IMUCLJOZSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(2R)-2-amino-4-[4-[(E)-C-[[(3S)-1-[(R)-carboxy-(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid
Database Links
Specialist databases
AntibioticDB 908
Other databases
CAS Registry No. 95927-71-2 (source: ChemIDplus)
GtoPdb PubChem SID 405560485
PubChem CID 9577949
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