Verrucarin A

Base Information

• Chemical Name: Verrucarin A
• CAS No.: 3148-09-2
• Molecular Formula: C27H34 O9
• Molecular Weight: 502.562
• Hs Code.: 2941900000
• European Community (EC) Number: 636-535-7
• UNII: OL62X66O4I
• DSSTox Substance ID: DTXSID101017607
• Wikipedia: Verrucarin_A
• Wikidata: Q1586727
• Metabolomics Workbench ID: 52739
• ChEMBL ID: CHEMBL136985
• Mol file: 3148-09-2.mol

Synonyms:muconomycin A;NSC 126,728;NSC 126728;verrucarin A

Chemical Property of Verrucarin A

Chemical Property:

• Vapor Pressure: 8.74E-26mmHg at 25°C
• Melting Point: >360° (dec)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 747.4°Cat760mmHg
• PKA: 12.76±0.70(Predicted)
• Flash Point: 250.2°C
• PSA: 120.89000
• Density: 1.32g/cm³
• LogP: 1.78050
• Storage Temp.: −20°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 0
• Exact Mass: 502.22028266
• Heavy Atom Count: 36
• Complexity: 1030

Purity/Quality:

98%,99%, ^*data from raw suppliers

Verrucarin A from Myrothecium sp. ≥98% (TLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: CC1CCOC(=O)C=CC=CC(=O)OC2CC3C4(C2(C5(CCC(=CC5O3)C)COC(=O)C1O)C)CO4
• Isomeric SMILES: C[C@@H]1CCOC(=O)/C=C/C=C\C(=O)O[C@@H]2C[C@@H]3[C@]4([C@]2([C@]5(CCC(=C[C@H]5O3)C)COC(=O)[C@H]1O)C)CO4
• Uses: Verrucarin A from Myrothecium sp has been used: as a translation initiation inhibitor in P. falciparum W2 strain as a peptidyl transfer inhibitor to test sensitivity in methyltransferase knock-out S. cerevisiae cellsto test its cytotoxicity in renal cell carcinoma cells

Technology Process of Verrucarin A

There total 5 articles about Verrucarin A 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:

trichoverrin B (76685-82-0,76739-70-3,145512-55-6,145512-56-7) → verrucarin A (3148-09-2) + isororidin E (16891-85-3,64726-84-7,89576-78-3) + roridin A (14729-29-4,84773-08-0) + verrucarin B (2290-11-1,92283-11-9,92283-12-0)

Guidance literature:

With M_. verrucaria; Product distribution; other trichoverrin;

DOI:10.1021/ja00392a044

Reference yield:

trichoverrin A (76739-70-3) → verrucarin A (3148-09-2) + roridin A (14729-29-4) + verrucarin J (4643-58-7) + Verrucarin B (2290-11-1,92283-11-9,92283-12-0)

Guidance literature:

In water; for 168h; Further byproducts given; mycelium of Myrothecium verrucaria;

DOI:10.1021/jo00345a044

Reference yield:

trichoverrin B (76685-82-0) → verrucarin A (3148-09-2) + roridin A (14729-29-4) + verrucarin J (4643-58-7) + Verrucarin B (2290-11-1,92283-11-9,92283-12-0)

Guidance literature:

In water; for 168h; Further byproducts given; mycelium of Myrothecium verrucaria;

DOI:10.1021/jo00345a044

upstream raw materials:

trichoverrin A

trichoverrin B

trichoverrin B

Downstream raw materials:

verrucarol

8α-hydroxyverrucarin A

4β,8β,15-trihydroxy-12,13-epoxytrichothecene

8-oxoverrucarin A

Refernces

• 1、 Jarvis, Bruce B.,Pavanasasivam, Gowsala,Holmlund, C. E.,DeSilva, Tuley,Stahly, G. Patrick,Mazzola, Eugene P.. "Biosynthetic Intermediates to the Macrocyclic Trichothecenes". . p. 472 - 474. Retrieved 2007/10/02.