BRL-42715   Click here for help

GtoPdb Ligand ID: 10993

Synonyms: C6-(N1-Methyl-1,2,3-trazolylmethylene)penem | LS-186900 (sodium salt) | LS-187554
Compound class: Synthetic organic
Comment: Strictly BRL-42715 is the sodium salt (PubChem CID 6436245); CAS number 102209-75-6) of the parent molecule provided here. BRL-42715 is a β-lactamase-inhibiting penem antibacterial [1,4-5].
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 6
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 124.48
Molecular weight 250.02
XLogP 0.01
No. Lipinski's rules broken 0
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 O=C1/C(=C\c2c[nH]nn2)/[C@@H]2N1C(=CS2)C(=O)O
Isomeric SMILES O=C1/C(=C\c2c[nH]nn2)/[C@@H]2N1C(=CS2)C(=O)O
InChI InChI=1S/C9H6N4O3S/c14-7-5(1-4-2-10-12-11-4)8-13(7)6(3-17-8)9(15)16/h1-3,8H,(H,15,16)(H,10,11,12)/b5-1+/t8-/m1/s1
InChI Key WFUNKYVUHIZWEW-VRFQNRHZSA-N
References
1. Aldridge KE. (1993)
A new potent beta-lactamase inhibitor, BRL 42715, with inherent activity against Bacteroides fragilis group strains.
Clin Infect Dis, 16 Suppl 4: S335-8. [PMID:8324143]
2. Appelbaum PC, Spangler SK, Shiman R, Jacobs MR. (1992)
Susceptibilities of 540 anaerobic gram-negative bacilli to amoxicillin, amoxicillin-BRL 42715, amoxicillin-clavulanate, temafloxacin, and clindamycin.
Antimicrob Agents Chemother, 36 (5): 1140-3. [PMID:1324639]
3. Ephtimios IE, Barrett MS, Wenzel RP, Jones RN. (1992)
In-vitro antimicrobial activity of the penem BRL-42715, alone and in combination with ampicillin, against respiratory tract pathogens.
J Antimicrob Chemother, 29 (5): 599-600. [PMID:1624400]
4. Farmer TH, Page JW, Payne DJ, Knowles DJ. (1994)
Kinetic and physical studies of beta-lactamase inhibition by a novel penem, BRL 42715.
Biochem J, 303 ( Pt 3): 825-30. [PMID:7980451]
5. Muratani T, Yokota E, Nakane T, Inoue E, Mitsuhashi S. (1993)
In-vitro evaluation of the four beta-lactamase inhibitors: BRL42715, clavulanic acid, sulbactam, and tazobactam.
J Antimicrob Chemother, 32 (3): 421-9. [PMID:8262864]