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chlorhexidine   Click here for help

GtoPdb Ligand ID: 14052

Approved drug PDB Ligand
chlorhexidine is an approved drug (FDA (1976), UK)
Compound class: Synthetic organic
Comment: Chlorhexidine is a bisbiguanide compound with broad-spectrum antimicrobial activity, including against Gram-negative and Gram-positive bacteria [1]. It is exploited for its topical antiseptic utility and is included in the World Health Organization's Model List of Essential Medicines (link provided in the Classification table, under the Summary tab below) for use as an antiseptic.
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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Click here for structure editor
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 10
Hydrogen bond donors 6
Rotatable bonds 13
Topological polar surface area 177.58
Molecular weight 505.45
XLogP 1.15
No. Lipinski's rules broken 3

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 C(CCCN=C(N)/N=C(\N)/NC1=CC=C(C=C1)Cl)CCN=C(N)/N=C(\N)/NC2=CC=C(C=C2)Cl
Isomeric SMILES C1=CC(=CC=C1N/C(=N/C(=NCCCCCCN=C(/N=C(/NC2=CC=C(C=C2)Cl)\N)N)N)/N)Cl
InChI InChI=1S/C22H30Cl2N10/c23-15-5-9-17(10-6-15)31-21(27)33-19(25)29-13-3-1-2-4-14-30-20(26)34-22(28)32-18-11-7-16(24)8-12-18/h5-12H,1-4,13-14H2,(H5,25,27,29,31,33)(H5,26,28,30,32,34)
InChI Key GHXZTYHSJHQHIJ-UHFFFAOYSA-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. DAVIES GE, FRANCIS J, MARTIN AR, ROSE FL, SWAIN G. (1954)
1:6-Di-4'-chlorophenyldiguanidohexane (hibitane); laboratory investigation of a new antibacterial agent of high potency.
Br J Pharmacol Chemother, 9 (2): 192-6. [PMID:13172429]
2. Risso D, Behrens M, Sainz E, Meyerhof W, Drayna D. (2017)
Probing the Evolutionary History of Human Bitter Taste Receptor Pseudogenes by Restoring Their Function.
Mol Biol Evol, 34 (7): 1587-1595. [PMID:28333344]