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SMT-738   Click here for help

GtoPdb Ligand ID: 14289

Synonyms: SMT-026738
Compound class: Synthetic organic
Comment: SMT-738 is from a novel class of antibacterial compounds that have activity against carbapenem-resistant Enterobacteriaceae (CREs) [1]. The structure is claimed in patent WO2022233886A1 that was filed by Discuva Ltd. (acquired by Summit Therapeutics in 2017) [2]. Functionally, it inhibits LolCDE [1], a complex that is essential for the transport of lipoproteins from the inner membrane to the outer membrane of Gram-negative bacteria.
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 4
Topological polar surface area 118.33
Molecular weight 392.46
XLogP -0.11
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 CC1=C(C=CN=C1)C2=C(C3=CC=C4C(=C3)N(CCO4)C(=O)C(C)(C)N)N=C(N)N2
Isomeric SMILES CC1=C(C=CN=C1)C2=C(N=C(N2)N)C3=CC4=C(C=C3)OCCN4C(=O)C(C)(C)N
InChI InChI=1S/C21H24N6O2/c1-12-11-24-7-6-14(12)18-17(25-20(22)26-18)13-4-5-16-15(10-13)27(8-9-29-16)19(28)21(2,3)23/h4-7,10-11H,8-9,23H2,1-3H3,(H3,22,25,26)
InChI Key JPOVQSBUKRMDME-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-amino-1-[6-[2-amino-5-(3-methyl-4-pyridinyl)-1H-imidazol-4-yl]-2,3-dihydro-1,4-benzoxazin-4-yl]-2-methylpropan-1-one
Synonyms Click here for help
SMT-026738
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo SMT-738
Other databases
CAS Registry No. 2862851-15-6 (source: Scifinder)
PubChem CID 166107891
Search Google for chemical match using the InChIKey JPOVQSBUKRMDME-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JPOVQSBUKRMDME
UniChem Compound Search for chemical match using the InChIKey JPOVQSBUKRMDME-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JPOVQSBUKRMDME-UHFFFAOYSA-N