(5Z)-7-Oxozeaenol - ≥98%(HPLC), high purity , CAS No.253863-19-3, Inhibitor of mitogen-activated protein kinase kinase kinase 7

Item Number
Z286693
Grouped product items
SKUSizeAvailabilityPrice Qty
Z286693-1mg
1mg
Available within 8-12 weeks(?)
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$246.90

Potent and selective TAK1 MAPKKK inhibitor

Basic Description

Synonyms5Z-7-Oxozeaenol | AKOS030213203 | 5Z-7-Oxozeaenol, >=98% (HPLC) | NCGC00186421-07 | N-iodosuccinic acid imide | BDBM50042034 | LL-Z1640-2 | SCHEMBL3841555 | HY-12686 | FR148083 | FR-148083 | CS-0012266 | CHEBI:67559 | Q27074007 | L783279 | (2E,5S,6S,8Z,11
Specifications & PurityMoligand™, ≥98%(HPLC)
Biochemical and Physiological MechanismsResorcyclic lactone of fungal origin that acts as a potent and selective transforming growth factor-β-activated kinase 1 (TAK1) mitogen-activated protein kinase kinase kinase (MAPKKK) inhibitor (IC50= 8 nM). Displays > 33-fold and > 62-fold selectivity ov
Storage TempStore at -20°C,Desiccated
Shipped InIce chest + Ice pads
GradeMoligand™
Action TypeINHIBITOR
Mechanism of actionInhibitor of mitogen-activated protein kinase kinase kinase 7

Associated Targets(Human)

RELA Tchem Transcription factor p65 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
PLAA Tchem Phospholipase A-2-activating protein (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
MAP3K7 Tchem Mitogen-activated protein kinase kinase kinase 7 (5 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
MAP2K1 Tclin Dual specificity mitogen-activated protein kinase kinase 1 (2 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ERBB2 Tclin Receptor protein-tyrosine kinase erbB-2 (7851 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDGFRB Tclin Platelet-derived growth factor receptor beta (5195 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KIT Tclin Stem cell growth factor receptor (10667 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKDC Tchem DNA-dependent protein kinase (1929 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCZ Tchem Protein kinase C zeta (2414 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP2K6 Tchem Dual specificity mitogen-activated protein kinase kinase 6 (1284 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FGFR1 Tclin Fibroblast growth factor receptor 1 (9149 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
STK3 Tchem Serine/threonine-protein kinase MST2 (3069 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP2K5 Tchem Dual specificity mitogen-activated protein kinase kinase 5 (650 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAMK2B Tchem CaM kinase II beta (1626 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP2K3 Tchem Dual specificity mitogen-activated protein kinase kinase 3 (632 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK6 Tclin Cyclin-dependent kinase 6 (1724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHEK2 Tchem Serine/threonine-protein kinase Chk2 (4015 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA2 Tchem AMP-activated protein kinase, alpha-2 subunit (1328 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRK2 Tchem G-protein coupled receptor kinase 2 (1019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHUK Tchem Inhibitor of nuclear factor kappa B kinase alpha subunit (3170 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IKBKB Tchem Inhibitor of nuclear factor kappa B kinase beta subunit (5554 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKB Tchem Serine/threonine-protein kinase Aurora-B (6805 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPS6KA4 Tchem Ribosomal protein S6 kinase alpha 4 (2104 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CSK Tchem Tyrosine-protein kinase CSK (2395 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAF1 Tclin Serine/threonine-protein kinase RAF (4169 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
JAK1 Tclin Tyrosine-protein kinase JAK1 (8569 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPS6KA1 Tchem Ribosomal protein S6 kinase alpha 1 (2796 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPS6KA6 Tchem Ribosomal protein S6 kinase alpha 6 (2027 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAMK1 Tchem CaM kinase I alpha (1664 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAMK4 Tbio CaM kinase IV (2116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT1 Tclin Vascular endothelial growth factor receptor 1 (6262 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3A Tclin Glycogen synthase kinase-3 alpha (3764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP2K2 Tclin Dual specificity mitogen-activated protein kinase kinase 2 (1262 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP2K4 Tchem Dual specificity mitogen-activated protein kinase kinase 4 (1051 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK13 Tchem MAP kinase p38 delta (2605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA1 Tclin AMP-activated protein kinase, alpha-1 subunit (2493 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MST1R Tchem Macrophage-stimulating protein receptor (2327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MTOR Tclin Serine/threonine-protein kinase mTOR (13850 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK10 Tchem c-Jun N-terminal kinase 3 (3396 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP2K1 Tclin Dual specificity mitogen-activated protein kinase kinase 1 (4127 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MET Tclin Hepatocyte growth factor receptor (10718 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EPHB2 Tchem Ephrin type-B receptor 2 (1899 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAMK2D Tchem CaM kinase II delta (2813 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK3 Tchem MAP kinase ERK1 (4725 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Mapk1 MAP kinase ERK2 (650 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Camk2g CaM kinase II gamma (1 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Gck Hexokinase type IV (278 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycolicibacterium smegmatis (8003 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BaF3 (4657 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Blood (6 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (328 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name (4S,6Z,9S,10S,12E)-9,10,18-trihydroxy-16-methoxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,12,15,17-pentaene-2,8-dione
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
Canonical SMILES CC1CC=CC(=O)C(C(CC=CC2=C(C(=CC(=C2)OC)O)C(=O)O1)O)O
Isomeric SMILES C[C@H]1C/C=C\C(=O)[C@H]([C@H](C/C=C/C2=C(C(=CC(=C2)OC)O)C(=O)O1)O)O
Alternate CAS 253863-19-3
PubChem CID 9863776
MeSH Entry Terms 8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,9,10-tetrahydro-1H-benzo(c)(1)oxacyclotetradecine-1,7(8H)-dione;f152A1 compound;FR 148083;FR-148083;FR148083;LL Z1640-2;LL-Z1640-2
Molecular Weight 362.37

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

SolubilitySolvent:DMSO, Max Conc. mg/mL: 9.06, Max Conc. mM: 25

Safety and Hazards(GHS)

Pictogram(s) GHS06
Signal Danger
Hazard Statements

H301:Toxic if swallowed

Precautionary Statements

P321:Specific treatment (see ... on this label).

P405:Store locked up.

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P270:Do not eat, drink or smoke when using this product.

P330:Rinse mouth.

P301+P316:IF SWALLOWED: Get emergency medical help immediately.

Related Documents

References

1. 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]
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. 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,  (3): (643-50).  [PMID:23272696]

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