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253863-19-3

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253863-19-3 Structure

253863-19-3 Structure
IdentificationBack Directory
[Name]

LL Z1640-2
[CAS]

253863-19-3
[Synonyms]

C 292
FR148083
L 783279
f 152 A1
TAK1 inhibitor 5ZO)
5Z-7-Oxozeaenol >=98% (HPLC)
1H-2-Benzoxacyclotetradecin-1,7(8H)-dione, 3,4,9,10-tetrahydro-8,9,16-trihydroxy-14-methoxy-3-methyl-, (3S,5Z,8S,9S,11E)-
(2E,5S,6S,8Z,11S)-5,6,15-trihydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaene-7,13-dione
[Molecular Formula]

C19H22O7
[MDL Number]

MFCD12912700
[MOL File]

253863-19-3.mol
[Molecular Weight]

362.37
Chemical PropertiesBack Directory
[Melting point ]

171-173 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
[Boiling point ]

666.8±55.0 °C(Predicted)
[density ]

1.270±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: >10mg/mL
[form ]

powder
[pka]

7.32±0.70(Predicted)
[color ]

white to off-white
[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
[InChIKey]

NEQZWEXWOFPKOT-BYRRXHGESA-N
[SMILES]

COc1cc(O)c2C(=O)O[C@@H](C)CC=CC(=O)[C@@H](O)[C@@H](O)C\C=C\c2c1
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

45
[WGK Germany ]

3
[HS Code ]

3507909090
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

LL Z1640-2 (5Z-7-oxozeaenol) is a cis-enone resorcylic acid lactone first reported in 1978 and later rediscovered as an irreversible and highly selective TAK 1 inhibitor. TAK1 is a MAPKKK involved in the p38 signalling cascade for pro-inflammation signals such as cytokines. LL Z1640-2 effectively prevents inflammation in animal models.
[Definition]

ChEBI: 5Z-7-oxozeaenol is a macrolide that is the 7-oxo derivative of zeaenol (the 5Z stereoisomer). Isolated from Fungi, it exhibits cytotoxic, antibacterial and inhibitory activity against NF-kappaB. It has a role as a metabolite, an antibacterial agent, an antineoplastic agent and a NF-kappaB inhibitor. It is an aromatic ether, a macrolide, a member of phenols, a secondary alcohol and a secondary alpha-hydroxy ketone.
[Biochem/physiol Actions]

The anti-inflammatory effects of 5Z-7-oxozeaenol may affect cardiac hypertrophy.
[IC 50]

TAK1: 8.1 nM (IC50); MEK1: 411 nM (IC50); VEGFR-2: 52 nM (IC50); VEGFR-3: 110 nM (IC50); FLT3: 170 nM (IC50); PDGFR-β: 340 nM (IC50); B-RAF VE: 6300 nM (IC50); SRC: 6600 nM (IC50)
[storage]

Desiccate at -20°C
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