CID 2920

Base Information

• Chemical Name: CID 2920
• CAS No.: 36011-19-5
• Molecular Formula: C28H33NO7
• Molecular Weight: 495.573
• Hs Code.: 29349990
• European Community (EC) Number: 252-835-7
• Wikipedia: Cytochalasin_E
• Wikidata: Q104170759,Q105148697
• Mol file: 36011-19-5.mol

Synonyms:cytochalasin E

Chemical Property of CID 2920

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 7.28E-21mmHg at 25°C
• Melting Point: 206 °C
• Refractive Index: 1.608
• Boiling Point: 705.057 °C at 760 mmHg
• Flash Point: 380.205 °C
• PSA: 114.46000
• Density: 1.309 g/cm³
• LogP: 3.41770
• Storage Temp.: −20°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 495.22570239
• Heavy Atom Count: 36
• Complexity: 986

Purity/Quality:

97% ^*data from raw suppliers

Cytochalasin E ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+
• Hazard Codes: T+,T
• Statements: 26/27/28-63
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: CC1CC=CC2C3C(O3)(C(C4C2(C(=O)NC4CC5=CC=CC=C5)OC(=O)OC=CC(C1=O)(C)O)C)C
• Description: The cytochalasins are cell-permeable fungal metabolites which inhibit actin polymerization. This interferes with such diverse processes as cell movement, growth, phagocytosis, degranulation, and secretion. Cytochalasin E is an epoxide-containing analog of cytochalasin B which potently and selectively inhibits the growth of endothelial cells (IC50 < 1 nM), impairing angiogenesis and tumor growth. This cytochalasin does not inhibit glucose transport or HIV-1 protease activity.
• Uses: Cytochalasin E is one of a family of potent mycotoxins produced by a range of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, resulting in pronounced morphogenic changes in animals and plants. Despite the common mode of action, there is evidence that individual members display diverse selectivity. Specifically, cytochalasin E acts as an angiogenesis inhibitor and, unlike other cytochalasins, does not inhibit glucose transport. Cytochalasin E has been used as:a toxin to study its effects on avocado plantsa component of the incubating medium in feline junctional adhesion molecule 1 (fJAM-1) expression assay an inhibitor of actin polymerization to study its effects on mitochondria uptake by mice endothelial cells Cytochalasin E is a fungal metabolite which has been shown to exhibit antimicrobial and antibacterial effects. Cytochalasin E is a microfilament inhibitor enhancing the low-affinity Fc epsilon receptor (CD23) expression.

Technology Process of CID 2920

There total 2 articles about CID 2920 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ cytochalasin E (36011-19-5)

Guidance literature:

With PD-medium; at 25 ℃; for 1440h;

DOI:10.1248/cpb.37.2212

Reference yield:

cytochalasin Z16 → 5,6-dehydro-7-hydroxycytochalasin E + cytochalasin E (36011-19-5)

Guidance literature:

With Aspergillus clavatus ΔccsB-37 strain; Enzymatic reaction;

DOI:10.1038/nchembio.1527

Reference yield: 79.0%

cytochalasin E (36011-19-5) → (1S,3aS,6R,7S,7aS)-1-benzyl-3a,6-dihydroxy-6,7-dimethyl-3-oxo-2,3,3a,6,7,7a-hexahydro-1H-isoindole-4-carbaldehyde

Guidance literature:

With pyridine; ozone; In methanol; at -78 - 20 ℃; for 4h;

DOI:10.1016/j.bmc.2016.12.005

Downstream raw materials:

(3aS)-3c-benzyl-5c,6c-epoxy-7a-hydroxy-7t-hydroxymethyl-4t,5t-dimethyl-(3ar,7ac)-octahydro-isoindol-1-one

Carbonic acid (1aR,2S,3S,5aS,6S,6aS)-3-benzyl-6-((E)-(4S,6S)-6-hydroxy-4,6-dimethyl-5,8-dioxo-oct-1-enyl)-1a,2-dimethyl-5-oxo-octahydro-1-oxa-4-aza-cyclopropa[f]inden-5a-yl ester methyl ester

7,18-dihydroxy-16,18-dimethyl-10-phenyl-21,23-dioxo<13>-cytochalasa-6(12),13(E),19(E)triene-1,17,22-trione

cytochalasin K