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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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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-{5-amino-7-methyl-2,6,7,9,11-pentaazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,5,8,10-pentaen-2-yl}-5-(hydroxymethyl)oxolane-3,4-diol
International Nonproprietary Names Click here for help
INN number INN
5115 triciribine
Synonyms Click here for help
Akt inhibitor V | Akt/protein kinase B signaling inhibitor-2 | API-2 | NSC-154020 | tricyclic nucleoside (TCN)
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-2404226
Reactome Reaction Reactome logo R-HSA-2400010
Other databases
CAS Registry No. 35943-35-2
ChEMBL Ligand CHEMBL1892348
GtoPdb PubChem SID 178102543
PubChem CID 290486
Search Google for chemical match using the InChIKey HOGVTUZUJGHKPL-UHFFFAOYSA-N
Search Google for chemicals with the same backbone HOGVTUZUJGHKPL
Search PubMed clinical trials triciribine
Search PubMed titles triciribine
Search PubMed titles/abstracts triciribine
UniChem Compound Search for chemical match using the InChIKey HOGVTUZUJGHKPL-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey HOGVTUZUJGHKPL-UHFFFAOYSA-N