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LL Z1640-2

LL Z1640-2 structure

CAS No:
253863-19-3
Formula:
C19H22O7
Chemical Name:
LL Z1640-2
Synonyms:
f 152 A1;(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;C 292;FR148083;L 783279;TAK1 inhibitor 5ZO);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)-;5Z-7-Oxozeaenol >=98% (HPLC)
Categories:
Organic Chemistry > Lactones

Description

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

LL Z1640-2 Basic Attributes

Molecular Weight：

362.37

Exact Mass：

362.37

DSSTox ID：

DTXSID90432058

Color/Form：

white to off-white

HScode：

3507909090

Characteristics

Density：

1.270±0.06 g/cm3(Predicted)

Melting Point：

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

Boiling Point：

666.8±55.0 °C(Predicted)

PKA：

7.32±0.70(Predicted)

Critical Temperature & Pressure：

2-8°C

Safety Information

wgk germany：

hazard class code：

safety instructions：

Marks：

Storage features：

Desiccate at -20°C

Hazard Statements：

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

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

LL Z1640-2 Use and Manufacturing

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.

(5Z)-7-Oxozeaenol is a highly potent inhibitor of TAK1, which is a member of the mitogen-acitvated kinase kinase kinase (MAPKKK) family. 5Z-7-Oxozeaenol blocked interleukin-1-induced activation of TAK1, JNK/p38 MAPK, IκB kinases, and NF-κB, resulting in inhibition of cyclooxgenase-2 production.

Computed Properties

Molecular Weight:362.4
XLogP3:2.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:1
Exact Mass:362.13655304
Monoisotopic Mass:362.13655304
Topological Polar Surface Area:113
Heavy Atom Count:26
Complexity:556
Defined Atom Stereocenter Count:3
Defined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes