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
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Molecular structure representations generated using Open Babel