AZD8055   Click here for help

GtoPdb Ligand ID: 7714

Synonyms: AZD 8055 | AZD-8055
Compound class: Synthetic organic
Comment: AZD8055 is an inhibitor of the mammalian target of rapamycin (mTOR) kinase [1]. AZD8055 was investigated as a potential treatment for various types of relapsed and/or refactory cancer. This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
Click here for help

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.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 93.07
Molecular weight 465.24
XLogP 3.41
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES OCc1cc(ccc1OC)c1ccc2c(n1)nc(nc2N1CCOCC1C)N1CCOCC1C
Isomeric SMILES OCc1cc(ccc1OC)c1ccc2c(n1)nc(nc2N1CCOC[C@@H]1C)N1CCOC[C@@H]1C
InChI InChI=1S/C25H31N5O4/c1-16-14-33-10-8-29(16)24-20-5-6-21(18-4-7-22(32-3)19(12-18)13-31)26-23(20)27-25(28-24)30-9-11-34-15-17(30)2/h4-7,12,16-17,31H,8-11,13-15H2,1-3H3/t16-,17-/m0/s1
InChI Key KVLFRAWTRWDEDF-IRXDYDNUSA-N
References
1. Chresta CM, Davies BR, Hickson I, Harding T, Cosulich S, Critchlow SE, Vincent JP, Ellston R, Jones D, Sini P et al.. (2010)
AZD8055 is a potent, selective, and orally bioavailable ATP-competitive mammalian target of rapamycin kinase inhibitor with in vitro and in vivo antitumor activity.
Cancer Res, 70 (1): 288-98. [PMID:20028854]
2. Datan E, Shirazian A, Benjamin S, Matassov D, Tinari A, Malorni W, Lockshin RA, Garcia-Sastre A, Zakeri Z. (2014)
mTOR/p70S6K signaling distinguishes routine, maintenance-level autophagy from autophagic cell death during influenza A infection.
Virology, 452-453: 175-90. [PMID:24606695]
3. Dittmar M, Lee JS, Whig K, Segrist E, Li M, Kamalia B, Castellana L, Ayyanathan K, Cardenas-Diaz FL, Morrisey EE et al.. (2021)
Drug repurposing screens reveal cell-type-specific entry pathways and FDA-approved drugs active against SARS-Cov-2.
Cell Rep, 35 (1): 108959. [PMID:33811811]
4. Fabrizio P, Pozza F, Pletcher SD, Gendron CM, Longo VD. (2001)
Regulation of longevity and stress resistance by Sch9 in yeast.
Science, 292 (5515): 288-90. [PMID:11292860]
5. Harrison DE, Strong R, Sharp ZD, Nelson JF, Astle CM, Flurkey K, Nadon NL, Wilkinson JE, Frenkel K, Carter CS et al.. (2009)
Rapamycin fed late in life extends lifespan in genetically heterogeneous mice.
Nature, 460 (7253): 392-5. [PMID:19587680]
6. Pike KG, Malagu K, Hummersone MG, Menear KA, Duggan HM, Gomez S, Martin NM, Ruston L, Pass SL, Pass M. (2013)
Optimization of potent and selective dual mTORC1 and mTORC2 inhibitors: the discovery of AZD8055 and AZD2014.
Bioorg Med Chem Lett, 23 (5): 1212-6. [PMID:23375793]
7. Robida-Stubbs S, Glover-Cutter K, Lamming DW, Mizunuma M, Narasimhan SD, Neumann-Haefelin E, Sabatini DM, Blackwell TK. (2012)
TOR signaling and rapamycin influence longevity by regulating SKN-1/Nrf and DAF-16/FoxO.
Cell Metab, 15 (5): 713-24. [PMID:22560223]
8. Sarbassov DD, Ali SM, Kim DH, Guertin DA, Latek RR, Erdjument-Bromage H, Tempst P, Sabatini DM. (2004)
Rictor, a novel binding partner of mTOR, defines a rapamycin-insensitive and raptor-independent pathway that regulates the cytoskeleton.
Curr Biol, 14 (14): 1296-302. [PMID:15268862]
9. Yang Z, Klionsky DJ. (2010)
Mammalian autophagy: core molecular machinery and signaling regulation.
Curr Opin Cell Biol, 22 (2): 124-31. [PMID:20034776]