triciribine   Click here for help

GtoPdb Ligand ID: 5920

Synonyms: Akt inhibitor V | Akt/protein kinase B signaling inhibitor-2 | API-2 | NSC-154020 | tricyclic nucleoside (TCN)
Compound class: Synthetic organic
Comment: The ligand image above represents this compound as used in the screens listed, and does not specify stereochemistry. The INN-assigned compound triciribine does have defined stereocentres and is represented by CID 65399.
Triciribine is an inhibitor of Akt signalling [3], HIV-1/2 [4], DNA synthesis [5] and exhibits in vitro and in vivo antitumour effects [6].
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 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 144.47
Molecular weight 320.12
XLogP 0.69
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 OCC1OC(C(C1O)O)n1cc2c3c1ncnc3n(nc2N)C
Isomeric SMILES OCC1OC(C(C1O)O)n1cc2c3c1ncnc3n(nc2N)C
InChI InChI=1S/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)
InChI Key HOGVTUZUJGHKPL-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/)

Large-scale screening data

EMD Millipore KinaseProfilerTM screen/Reaction Biology Kinase HotspotSM screen Click here for help
A screen profiling 158 kinase inhibitors (Calbiochem Protein Kinase Inhibitor Library I and II, catalogue numbers 539744 and 539745) for their inhibitory activity at 1µM and 10µM against 234 human recombinant kinases using the EMD Millipore KinaseProfilerTM service.

A screen profiling the inhibitory activity of 178 commercially available kinase inhibitors at 0.5µM against a panel of 300 recombinant protein kinases using the Reaction Biology Corporation Kinase HotspotSM platform.

http://www.millipore.com/techpublications/tech1/pf3036
http://www.reactionbiology.com/webapps/main/pages/kinase.aspx

Reference: 1-2
Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action % Activity remaining at 0.5µM % Activity remaining at 1µM % Activity remaining at 10µM
CDC like kinase 4 nd/CLK4 Hs Inhibitor Inhibition 80.4
protein kinase C alpha PKCα/PKCa Hs Inhibitor Inhibition 80.4 109.0 101.0
mitogen-activated protein kinase kinase kinase 2 nd/MEKK2 Hs Inhibitor Inhibition 86.3
beta adrenergic receptor kinase 2 nd/GRK3 Hs Inhibitor Inhibition 86.5
cyclin dependent kinase 2 CDK2/cyclin E Hs Inhibitor Inhibition 87.6
kinase insert domain receptor KDR/KDR(VEGFR2) Hs Inhibitor Inhibition 88.2 104.0 90.0
serine/threonine kinase 39 nd/STK39(STLK3) Hs Inhibitor Inhibition 88.3
receptor interacting serine/threonine kinase 2 RIPK2/RIPK2 Hs Inhibitor Inhibition 88.3 83.0 91.0
p21 (RAC1) activated kinase 1 nd/PAK1 Hs Inhibitor Inhibition 88.6
homeodomain interacting protein kinase 3 HIPK3/HIPK3 Hs Inhibitor Inhibition 89.5 100.0 97.0
Displaying the top 10 targets  View all targets in screen »