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 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 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
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 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
References
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat Biotechnol, 29 (11): 1039-45. [PMID:22037377]
2. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem J, 451 (2): 313-28. [PMID:23398362]
3. Gürsel DB, Connell-Albert YS, Tuskan RG, Anastassiadis T, Walrath JC, Hawes JJ, Amlin-Van Schaick JC, Reilly KM. (2011)
Control of proliferation in astrocytoma cells by the receptor tyrosine kinase/PI3K/AKT signaling axis and the use of PI-103 and TCN as potential anti-astrocytoma therapies.
Neuro-oncology, 13 (6): 610-21. [PMID:21636709]
4. Ptak RG, Borysko KZ, Porcari AR, Buthod JL, Holland LE, Shipman Jr C, Townsend LB, Drach JC. (1998)
Phosphorylation of triciribine is necessary for activity against HIV type 1.
AIDS Res Hum Retroviruses, 14 (15): 1315-22. [PMID:9788672]
5. Wotring LL, Townsend LB, Jones LM, Borysko KZ, Gildersleeve DL, Parker WB. (1990)
Dual mechanisms of inhibition of DNA synthesis by triciribine.
Cancer Res, 50 (16): 4891-9. [PMID:2379153]
6. Yang L, Dan HC, Sun M, Liu Q, Sun XM, Feldman RI, Hamilton AD, Polokoff M, Nicosia SV, Herlyn M et al.. (2004)
Akt/protein kinase B signaling inhibitor-2, a selective small molecule inhibitor of Akt signaling with antitumor activity in cancer cells overexpressing Akt.
Cancer Res, 64 (13): 4394-9. [PMID:15231645]