LUNA18   Click here for help

GtoPdb Ligand ID: 12931

Synonyms: compound 45 [PMID: 37463267]
Compound class: Peptide
Comment: LUNA18 is an 11-mer cyclic peptide that acts as a KRAS inhibitor [1]. Individual amino acids have been modified to optimise target selectivity and membrane permeability. LUNA18 inhibits the KRASG12D-Son of Sevenless (SOS) protein-protein interaction (IC50 <2 nM) and is orally bio-active in xenograft models bearing mutant KRAS tumours.
The SMILES for LUNA18 was generated using the compound's image from [1] and the DECIMER web application (decimer.ai).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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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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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 CC[C@H](C)[C@@H](C(=O)N(C)[C@@H](C)C(=O)N1CC[C@H]1C(=O)N(CC)[C@@H](CC2=CC=C(C)C=C2)C(=O)N(C)CC(=O)N[C@@H](CCC3=CC(=C(C(=C3)F)C(F)(F)F)F)C(=O)N4CCC[C@H]4C(=O)NC5(CCCC5)C(=O)N(C)[C@@H](C6CCCC6)C(=O)N(C)[C@@H](CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N(C)C)C(=O)N(C)C)N
Isomeric SMILES CC[C@H](C)[C@H](N)C(=O)N(C)[C@@H](C)C(=O)N1CC[C@H]1C(=O)N(CC)[C@@H](CC2=CC=C(C)C=C2)C(=O)N(C)CC(=O)N[C@@H](CCC3=CC(F)=C(C(F)=C3)C(F)(F)F)C(=O)N4CCC[C@H]4C(=O)NC5(CCCC5)C(=O)N(C)[C@@H](C6CCCC6)C(=O)N(C)[C@@H](CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N(C)C)C(=O)N(C)C
InChI InChI=1S/C81H123F5N14O13/c1-19-49(7)66(87)76(110)94(15)51(9)71(105)100-40-36-59(100)75(109)98(21-3)62(44-52-32-30-48(6)31-33-52)74(108)93(14)46-63(101)88-57(35-34-53-42-55(82)65(56(83)43-53)81(84,85)86)72(106)99-39-26-29-58(99)70(104)90-80(37-24-25-38-80)79(113)97(18)68(54-27-22-23-28-54)78(112)96(17)61(73(107)91(10)11)45-64(102)95(16)60(41-47(4)5)69(103)89-67(50(8)20-2)77(111)92(12)13/h30-33,42-43,47,49-51,54,57-62,66-68H,19-29,34-41,44-46,87H2,1-18H3,(H,88,101)(H,89,103)(H,90,104)/t49-,50-,51-,57-,58-,59-,60-,61-,62-,66-,67-,68-/m0/s1
InChI Key VXOYCRDXTBEJEX-GKFACYGMSA-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 Peptide
IUPAC Name Click here for help
(2S)-2-[(2S)-2-(1-{1-[(2S)-1-[(2S)-2-{2-[(2S)-2-{1-[(2S)-1-[(2S)-2-[(2S,3S)-2-amino-N,3-dimethylpentanamido]propanoyl]azetidin-2-yl]-N-ethylformamido}-N-methyl-3-(4-methylphenyl)propanamido]acetamido}-4-[3,5-difluoro-4-(trifluoromethyl)phenyl]butanoyl]pyrrolidine-2-amido]cyclopentyl}-N-methylformamido)-2-cyclopentyl-N-methylacetamido]-N'-[(1S)-1-{[(1S,2S)-1-(dimethylcarbamoyl)-2-methylbutyl]carbamoyl}-3-methylbutyl]-N,N,N'-trimethylbutanediamide
Synonyms Click here for help
compound 45 [PMID: 37463267]
Database Links Click here for help
GtoPdb PubChem SID 485206052
PubChem CID 169422743
Search Google for chemical match using the InChIKey VXOYCRDXTBEJEX-GKFACYGMSA-N
Search Google for chemicals with the same backbone VXOYCRDXTBEJEX
UniChem Compound Search for chemical match using the InChIKey VXOYCRDXTBEJEX-GKFACYGMSA-N
UniChem Connectivity Search for chemical match using the InChIKey VXOYCRDXTBEJEX-GKFACYGMSA-N