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CGP-31608   Click here for help

GtoPdb Ligand ID: 10963

Synonyms: CGP 31608 | CGP31608
Compound class: Synthetic organic
Comment: CGP 31608 is a semisynthetic penem derived antibacterial, with Gram-positive and Gram-negative activities [1-3].
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 6
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 129.16
Molecular weight 244.05
XLogP -3.58
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 NCC1=C(C(=O)O)N2[C@H](S1)[C@H](C2=O)[C@H](O)C
Isomeric SMILES NCC1=C(C(=O)O)N2[C@H](S1)[C@H](C2=O)[C@H](O)C
InChI InChI=1S/C9H12N2O4S/c1-3(12)5-7(13)11-6(9(14)15)4(2-10)16-8(5)11/h3,5,8,12H,2,10H2,1H3,(H,14,15)/t3-,5+,8-/m1/s1
InChI Key RXCNILVLOHRALM-UWBRJAPDSA-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. Neu HC, Chin NX, Neu NM. (1987)
In vitro activity and beta-lactamase stability of a new penem, CGP 31608.
Antimicrob Agents Chemother, 31 (4): 558-69. [PMID:3496845]
2. Wise R, Andrews JM, Piddock LJ. (1987)
In vitro activity of CGP 31608, a new penem.
Antimicrob Agents Chemother, 31 (2): 267-73. [PMID:3105451]
3. Wise R, Webberley JM, Andrews JM, Ashby JP. (1988)
The pharmacokinetics and tissue penetration of intravenously administered CGP 31608.
J Antimicrob Chemother, 21 (1): 85-91. [PMID:3356625]