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NAV2729   Click here for help

GtoPdb Ligand ID: 14182

Synonyms: Grassofermata | NAV-2729
Compound class: Synthetic organic
Comment: NAV2729 is an ARF6 inhibitor tool compound [1-5]. It has an allosteric, non-nucleotide-competitive mode of action [4].
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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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View interactive charts of activity data across species
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 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 87.84
Molecular weight 456.88
XLogP 4.32
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 C1=CC=C(C=C1)CC2=NN3C(=O)C=C(C4=CC=C(C=C4)[N+](=O)[O-])NC3=C2C5=CC=C(C=C5)Cl
Isomeric SMILES O=C1C=C(C2=CC=C([N+]([O-])=O)C=C2)NC3=C(C4=CC=C(Cl)C=C4)C(CC5=CC=CC=C5)=NN13
InChI InChI=1S/C25H17ClN4O3/c26-19-10-6-18(7-11-19)24-22(14-16-4-2-1-3-5-16)28-29-23(31)15-21(27-25(24)29)17-8-12-20(13-9-17)30(32)33/h1-13,15,27H,14H2
InChI Key GUUWHOSUKOCRHG-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. Benabdi S, Peurois F, Nawrotek A, Chikireddy J, Cañeque T, Yamori T, Shiina I, Ohashi Y, Dan S, Rodriguez R et al.. (2017)
Family-wide Analysis of the Inhibition of Arf Guanine Nucleotide Exchange Factors with Small Molecules: Evidence of Unique Inhibitory Profiles.
Biochemistry, 56 (38): 5125-5133. [PMID:28858527]
2. Wang R, Schneider S, Keppler OT, Li B, Rutz B, Ciotkowska A, Stief CG, Hennenberg M. (2021)
ADP Ribosylation Factor 6 Promotes Contraction and Proliferation, Suppresses Apoptosis and Is Specifically Inhibited by NAV2729 in Prostate Stromal Cells.
Mol Pharmacol, 100 (4): 356-371. [PMID:34349027]
3. Yamauchi Y, Miura Y, Kanaho Y. (2017)
Machineries regulating the activity of the small GTPase Arf6 in cancer cells are potential targets for developing innovative anti-cancer drugs.
Adv Biol Regul, 63: 115-121. [PMID:27776975]
4. Yoo JH, Shi DS, Grossmann AH, Sorensen LK, Tong Z, Mleynek TM, Rogers A, Zhu W, Richards JR, Winter JM et al.. (2016)
ARF6 Is an Actionable Node that Orchestrates Oncogenic GNAQ Signaling in Uveal Melanoma.
Cancer Cell, 29 (6): 889-904. [PMID:27265506]
5. Yu Q, Gratzke C, Wang R, Li B, Kuppermann P, Herlemann A, Tamalunas A, Wang Y, Rutz B, Ciotkowska A et al.. (2019)
A NAV2729-sensitive mechanism promotes adrenergic smooth muscle contraction and growth of stromal cells in the human prostate.
J Biol Chem, 294 (32): 12231-12249. [PMID:31243101]