5Z-7-oxozeaenol   Click here for help

GtoPdb Ligand ID: 8077

Synonyms: (5Z)-7-oxozeaenol | FR-148083 [1] | LL-Z1640-2
PDB Ligand
Compound class: Synthetic organic
Comment: 5Z-7-oxozeaenol is a cell-permeable fungal resorcylic lactone. 5Z-7-oxozeaenol acts as a selective and potent inhibitor of mitogen-activated protein kinase kinase kinase 7 (TAK1). This compound binds covalently/irreversibly and inhibits both the ATPase and kinase activity of TAK1 [4].
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 5
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 113.29
Molecular weight 362.14
XLogP 2.25
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 COc1cc2C=CCC(O)C(O)C(=O)C=CCC(OC(=O)c2c(c1)O)C
Isomeric SMILES COc1cc2/C=C/C[C@H](O)[C@H](O)C(=O)/C=C\C[C@@H](OC(=O)c2c(c1)O)C
InChI InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15-,18+/m0/s1
InChI Key NEQZWEXWOFPKOT-BYRRXHGESA-N
References
1. Barf T, Kaptein A. (2012)
Irreversible protein kinase inhibitors: balancing the benefits and risks.
J Med Chem, 55 (14): 6243-62. [PMID:22621397]
2. Ninomiya-Tsuji J, Kajino T, Ono K, Ohtomo T, Matsumoto M, Shiina M, Mihara M, Tsuchiya M, Matsumoto K. (2003)
A resorcylic acid lactone, 5Z-7-oxozeaenol, prevents inflammation by inhibiting the catalytic activity of TAK1 MAPK kinase kinase.
J Biol Chem, 278 (20): 18485-90. [PMID:12624112]
3. Rawlins P, Mander T, Sadeghi R, Hill S, Gammon G, Foxwell B, Wrigley S, Moore M. (1999)
Inhibition of endotoxin-induced TNF-alpha production in macrophages by 5Z-7-oxo-zeaenol and other fungal resorcylic acid lactones.
Int J Immunopharmacol, 21 (12): 799-814. [PMID:10606001]
4. Wu J, Powell F, Larsen NA, Lai Z, Byth KF, Read J, Gu RF, Roth M, Toader D, Saeh JC et al.. (2013)
Mechanism and In Vitro Pharmacology of TAK1 Inhibition by (5Z)-7-Oxozeaenol.
ACS Chem Biol, 8 (3): 643-50. [PMID:23272696]