apalcillin   Click here for help

GtoPdb Ligand ID: 10759

Synonyms: PC-904 | PC904 | WY-44,417 | WY-44417
Compound class: Synthetic organic
Comment: Apalcillin (PC-904) is a semisynthetic penicillin (β-lactam) derivative antibiotic [1-2]. It is highly active against Pseudomonas species. Toxicity issues meant that this compound did not progress beyond preclinical evaluation.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 186.86
Molecular weight 521.14
XLogP 0.66
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C([C@@H](c1ccccc1)NC(=O)c1c[nH]c2c(c1=O)nccc2)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
Isomeric SMILES O=C([C@@H](c1ccccc1)NC(=O)c1c[nH]c2c(c1=O)nccc2)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI InChI=1S/C25H23N5O6S/c1-25(2)19(24(35)36)30-22(34)17(23(30)37-25)29-21(33)15(12-7-4-3-5-8-12)28-20(32)13-11-27-14-9-6-10-26-16(14)18(13)31/h3-11,15,17,19,23H,1-2H3,(H,27,31)(H,28,32)(H,29,33)(H,35,36)/t15-,17-,19+,23-/m1/s1
InChI Key XMQVYNAURODYCQ-SLFBBCNNSA-N
Bioactivity Comments
PC-904 is reported to be 35 and 100 times more active than carbenicillin against Pseudomonas aeruginosa and Klebsiella pneumoniae respectively, and its MICs against P. aeruginosa are comparable to those of gentamicin [1],