O9890
5Z-7-Oxozeaenol
≥98% (HPLC), powder, TAK1 inhibitor
Synonym(s):
C 292, F 152, FR148083, L 783279, LL-Z1640-2
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About This Item
Empirical Formula (Hill Notation):
C19H22O7
CAS Number:
Molecular Weight:
362.37
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
5Z-7-Oxozeaenol, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to off-white
solubility
DMSO: >10 mg/mL
storage temp.
2-8°C
SMILES string
COc1cc(O)c2C(=O)O[C@@H](C)CC=CC(=O)[C@@H](O)[C@@H](O)C\C=C\c2c1
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
Application
5Z-7-Oxozeaenol has been used:
- as transforming growth factor β-activated kinase 1 (TAK1) inhibitor to treat human colon cancer cells
- as TAK1-specific inhibitor to provide intraperitoneal injection to mice for aortic banding
- as TAK1 inhibitor to treat cells for luciferase reporter assay
- to test growth and differentiation factor 2 (GDF2)-mediated anoikis
Biochem/physiol Actions
5Z-7-oxozeaenol is a potent ATP-competitive irreversible inhibitor of ERK2 (IC50 = 80 nM), TAK1 (MEKK7), MKK7, and MEK1, which all contain a common cysteine residue in the ATP-binding site. 5Z-7-oxozeaenol has no activity against other MAP kinases. 5Z-7-oxozeaenol is also anti-inflammatory.
The anti-inflammatory effects of 5Z-7-oxozeaenol may affect cardiac hypertrophy.
Features and Benefits
This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the MAPKKKs and MAPKs pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Li Bo et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 917-924 (2016-10-21)
Resistance to taxol represents a major obstacle for long-term remission in ovarian cancer. Transforming Growth Factor-β-Activated Kinase 1 (TAK1) is a critical component in immune response pathway. However, the role of TAK1 in the development of chemoresistance in ovarian cancer
Disruption of thioredoxin metabolism enhances the toxicity of transforming growth factor beta-activated kinase 1 (TAK1) inhibition in KRAS-mutated colon cancer cells
Hrabe JE, et al.
Redox Biology, 5, 319-327 (2015)
Dual-specificity phosphatase 14 protects the heart from aortic banding-induced cardiac hypertrophy and dysfunction through inactivation of TAK1-P38MAPK/-JNK1/2 signaling pathway
Li CY, et al.
Basic Research in Cardiology, 111(2), 19-19 (2016)