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Verrucarin A

CAT: 0804-HY-107426-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-107426-01Size:1 mg
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Description
Verrucarin A (Muconomycin A), a Type D macrocyclic mycotoxin derived from the pathogen fungus Myrothecium verrucaria, is an inhibitor of protein synthesis. Verrucarin A inhibits growth of leukemia cell lines and activates caspases and apoptosis and inflammatory signaling in macrophages. Verrucarin A effectively increased the phosphorylation of p38 MAPK and diminished the phosphorylation of ERK/Akt. Verrucarin A caused cell cycle deregulation through the induction of p21 and p53[1][2].
CAS Number
3148-09-2
Product Name Alternative
Muconomycin A
UNSPSC
12352005
Hazard Statement
H300, H310, H330
Target
Apoptosis; Reactive Oxygen Species (ROS)
Type
Reference compound
Related Pathways
Apoptosis; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/verrucarin-a.html
Purity
99.89
Solubility
DMSO : 10 mg/mL (ultrasonic; warming)
Smiles
C[C@@]12[C@]3(CO3)[C@@]4([H])C[C@@]1([H])OC(/C=C/C=C/C(OCC[C@@H](C)[C@H](O)C(OC[C@]25[C@](C=C(C)CC5)([H])O4)=O)=O)=O
Molecular Formula
C27H34O9
Molecular Weight
502.55
Precautions
H300, H310, H330
References & Citations
[1]Palanivel K, et al. Verrucarin A alters cell-cycle regulatory proteins and induces apoptosis through reactive oxygen species-dependent p38MAPK activation in the human breast cancer cell line MCF-7. Tumour Biol. 2014;35 (10) :10159-10167.|[2]Palanivel K, et al. Verrucarin A, a protein synthesis inhibitor, induces growth inhibition and apoptosis in breast cancer cell lines MDA-MB-231 and T47D. Biotechnol Lett. 2013;35 (9) :1395-1403.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Verrucarin A

Verrucarin A is a trichothecene antibiotic which incorporates a triester macrocyclic structure and an exocyclic methylene epoxide group. It is a macrotriolide, a macrolide antibiotic, an epoxide, an organic heterotetracyclic compound and a trichothecene.

CAS Number3148-09-2
PubChem CID6326658
IUPAC Name(1R,3R,8R,12S,13R,18E,20Z,24R,25S,26S)-12-hydroxy-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,17,22-trione
Molecular FormulaC27H34O9
Molecular Weight502.6
XLogP2.4
Topological Polar Surface Area121
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count0
Heavy Atom Count36
Formal Charge0
Complexity1030
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
InChI
InChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4+,7-5-/t17-,18-,19-,20-,23+,25-,26-,27+/m1/s1
InChIKey
NLUGUZJQJYVUHS-IDXDZYHTSA-N
Chemical Structure
2D Structure
2D structure of Verrucarin A
CAS: 3148-09-2
CID: 6326658
Formula: C27H34O9
MW: 502.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight502.6
XLogP32.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count0
Exact Mass502.22028266
Monoisotopic Mass502.22028266
Topological Polar Surface Area121 Ų
Heavy Atom Count36
Formal Charge0
Complexity1030
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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