benapenem   Click here for help

GtoPdb Ligand ID: 12793

Compound class: Synthetic organic
Comment: Benapenem is a carbapenem (β-lactam) with broad-spectrum antibacterial activity [2]. It has advanced to clinical evaluation as an intravenous treatment for urinary tract infections.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 11
Hydrogen bond donors 5
Rotatable bonds 9
Topological polar surface area 212.81
Molecular weight 524.61
XLogP -4.21
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H](C(=O)NCC4=CC=C(C=C4)S(=O)(=O)N)NC3)C(=O)O
Isomeric SMILES C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NCC4=CC=C(C=C4)S(=O)(=O)N)C(=O)O)[C@@H](C)O
InChI InChI=1S/C22H28N4O7S2/c1-10-17-16(11(2)27)21(29)26(17)18(22(30)31)19(10)34-13-7-15(24-9-13)20(28)25-8-12-3-5-14(6-4-12)35(23,32)33/h3-6,10-11,13,15-17,24,27H,7-9H2,1-2H3,(H,25,28)(H,30,31)(H2,23,32,33)/t10-,11-,13+,15+,16-,17-/m1/s1
InChI Key JNSMRGMLNPEWLR-PDCLSYJBSA-N
References
1. Ji XW, Xue F, Kang ZS, Zhong W, Kuan IH, Yang XP, Zhu X, Li Y, Lv Y. (2020)
Model-Informed Drug Development, Pharmacokinetic/Pharmacodynamic Cutoff Value Determination, and Antibacterial Efficacy of Benapenem against Enterobacteriaceae.
Antimicrob Agents Chemother, 64 (3). [PMID:31844001]
2. Zhao CY, Lv Y, Zhu Y, Wei MJ, Liu MY, Ji XW, Kang ZS, Xia YH, Tian JH, Ma Y et al.. (2019)
A First-in-Human Safety, Tolerability, and Pharmacokinetics Study of Benapenem in Healthy Chinese Volunteers.
Antimicrob Agents Chemother, 63 (3). [PMID:30617093]