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BRL-44154   Click here for help

GtoPdb Ligand ID: 11036

Synonyms: analogue 4f [Brown et al., 1991] [1] | BRL44154
Compound class: Synthetic organic
Comment: Strictly this is the parent molecule of BRL-44154 which referes to the sodium salt. BRL-44154 is a penicillin class antibacterial that was developed by SmithKline Beecham [2]. It has high stability to β-lactamases.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 8
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 200.75
Molecular weight 467.13
XLogP -1.03
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC(=O)[C@@H]1N2C(=O)C[C@H]([C@H]2SC1(C)C)NC(=O)/C(=N/OC1CCCC1)/c1csc(n1)N
Isomeric SMILES OC(=O)[C@@H]1N2C(=O)C[C@H]([C@H]2SC1(C)C)NC(=O)/C(=N/OC1CCCC1)/c1csc(n1)N
InChI InChI=1S/C19H25N5O5S2/c1-19(2)14(17(27)28)24-12(25)7-10(16(24)31-19)21-15(26)13(11-8-30-18(20)22-11)23-29-9-5-3-4-6-9/h8-10,14,16H,3-7H2,1-2H3,(H2,20,22)(H,21,26)(H,27,28)/b23-13+/t10-,14+,16-/m1/s1
InChI Key KNTUUEGDGYZCIA-ZUPSXRMKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Brown P, Calvert SH, Chapman PCA, Cosham SC, Eglington AJ, Elliot RL, Harris MA, Hinks JD, Lowther D, Merrikin DJ et al.. 
p- Lactamase-Stable Penicillins. Synthesis and Structure-Activity Relationships of (Z)-Alkyloxyimino Penicillins; Selection of BRL 441 54.
Accessed on 12/06/2020. Modified on 12/06/2020. pubs.rsc.org, https://pubs.rsc.org/en/content/articlepdf/1991/p1/p19910000881
2. Mizen L, Berry V, Woodnutt G. (1995)
The influence of uptake from the gastrointestinal tract and first-pass effect on oral bioavailability of (Z)-alkyloxyimino penicillins.
J Pharm Pharmacol, 47 (9): 725-30. [PMID:8583383]