KYT-0353   Click here for help

GtoPdb Ligand ID: 9347

Synonyms: COMPOUND-JP [US20160279103] [1] | JPH-203 | JPH203 | KYT0353
Compound class: Synthetic organic
Comment: KYT-0353 (JPH203) is a potent and selective inhibitor of L-type amino acid transporter 1 (SLC7A5) [2], that is being investigated as an anti-cancer agent. Structurally it is a tyrosine analog.
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 CDK toolkit. 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 5
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 124.6
Molecular weight 471.08
XLogP 1.81
No. Lipinski's rules broken 0
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.

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Canonical SMILES OC(=O)C(Cc1cc(Cl)c(c(c1)Cl)OCc1cc(N)cc2c1oc(n2)c1ccccc1)N
Isomeric SMILES OC(=O)[C@H](Cc1cc(Cl)c(c(c1)Cl)OCc1cc(N)cc2c1oc(n2)c1ccccc1)N
InChI InChI=1S/C23H19Cl2N3O4/c24-16-6-12(8-18(27)23(29)30)7-17(25)21(16)31-11-14-9-15(26)10-19-20(14)32-22(28-19)13-4-2-1-3-5-13/h1-7,9-10,18H,8,11,26-27H2,(H,29,30)/t18-/m0/s1
InChI Key XNRZJPQTMQZBCE-SFHVURJKSA-N
Bioactivity Comments
In preclinical studies KYT-0353 inhibits leucine uptake and cancer cell growth in vitro and markedly reduces tumor size in vivo [2-3]. Calculated IC50 for inhibition of leucine uptake was 140nM and 16400nM for inhibition of cell growth (using mouse renal proximal tubule cells expressing human LAT1) [2]. KYT-0353 does not inhibit leucine uptake via LAT2.
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
L-type amino acid transporter 1 Primary target of this compound Hs Inhibitor Inhibition - - - 2
⤷ [2]