ceftiolene   Click here for help

GtoPdb Ligand ID: 10784

Synonyms: 42980RP | cefatiolene | RP 42,980 | RP 42980 | RP-42980 | RP42980
Compound class: Synthetic organic
Comment: Ceftiolene is a semisynthetic, broad-spectrum, third-generation cephalosporin antibiotic [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 310.87
Molecular weight 594.04
XLogP -2.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=CCn1c(S/C=C/C2=C(C(=O)O)N3[C@H](SC2)[C@@H](C3=O)NC(=O)/C(=N\OC)/c2csc(n2)N)n[nH]c(=O)c1=O
Isomeric SMILES O=CCn1c(S/C=C/C2=C(C(=O)O)N3[C@H](SC2)[C@@H](C3=O)NC(=O)/C(=N\OC)/c2csc(n2)N)n[nH]c(=O)c1=O
InChI InChI=1S/C20H18N8O8S3/c1-36-26-10(9-7-39-19(21)22-9)13(30)23-11-15(32)28-12(18(34)35)8(6-38-17(11)28)2-5-37-20-25-24-14(31)16(33)27(20)3-4-29/h2,4-5,7,11,17H,3,6H2,1H3,(H2,21,22)(H,23,30)(H,24,31)(H,34,35)/b5-2+,26-10-/t11-,17-/m1/s1
InChI Key WJXAHFZIHLTPFR-JLRJEBFFSA-N
References
1. Williamson R, Gutmann L, Kitzis MD, Acar JF. (1984)
An evaluation of the bacteriolytic and biochemical properties of ceftiolene (42980RP).
J Antimicrob Chemother, 14 (6): 581-93. [PMID:6394571]