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EHT 1864   Click here for help

GtoPdb Ligand ID: 11059

Synonyms: EHT-1864 | EHT1864
Compound class: Synthetic organic
Comment: Potent Rac family inhibitor. Marketed as EHT 1864 dihydrochloride.
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 3
Hydrogen bond donors 0
Rotatable bonds 11
Topological polar surface area 90.1
Molecular weight 508.16
XLogP 4.64
No. Lipinski's rules broken 1

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 O=c1cc(occ1OCCCCCSc1ccnc2c1ccc(c2)C(F)(F)F)CN1CCOCC1
Isomeric SMILES O=c1cc(occ1OCCCCCSc1ccnc2c1ccc(c2)C(F)(F)F)CN1CCOCC1
InChI InChI=1S/C25H27F3N2O4S/c26-25(27,28)18-4-5-20-21(14-18)29-7-6-24(20)35-13-3-1-2-10-33-23-17-34-19(15-22(23)31)16-30-8-11-32-12-9-30/h4-7,14-15,17H,1-3,8-13,16H2
InChI Key MIDUFIRTIFUTQA-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. Onesto C, Shutes A, Picard V, Schweighoffer F, Der CJ. (2008)
Characterization of EHT 1864, a novel small molecule inhibitor of Rac family small GTPases.
Meth Enzymol, 439: 111-29. [PMID:18374160]
2. Shutes A, Onesto C, Picard V, Leblond B, Schweighoffer F, Der CJ. (2007)
Specificity and mechanism of action of EHT 1864, a novel small molecule inhibitor of Rac family small GTPases.
J Biol Chem, 282 (49): 35666-78. [PMID:17932039]