Verrucarin A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 573182

CAS#: 3148-09-2

Description: Verrucarin A is an antibiotic which has been shown to inhibit proliferation of prostate cancer cells by inhibiting prosurvival Akt/NF-kB/mTOR signaling.

Chemical Structure

Verrucarin A
CAS# 3148-09-2

Theoretical Analysis

MedKoo Cat#: 573182
Name: Verrucarin A
CAS#: 3148-09-2
Chemical Formula: C27H34O9
Exact Mass: 502.2203
Molecular Weight: 502.56
Elemental Analysis: C, 64.53; H, 6.82; O, 28.65

Price and Availability

Size Price Availability Quantity
1.0mg USD 275.0 2 Weeks
5.0mg USD 775.0 2 Weeks
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Synonym: Antibiotic 379Y, Muconomycin A, Verrucarin A

IUPAC/Chemical Name: Spiro(16,18-methano-1H,3H,23H-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyran-17(18H),2'-oxirane)-3,9,14-trione, 4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy-5,16a,21-trimethyl-, stereoisomer


InChi Code: 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

SMILES Code: C[C@@H]1CCOC(=O)\C=C\C=C/C(=O)O[C@@H]2C[C@H]3O[C@@H]4C=C(C)CC[C@]4(COC(=O)[C@H]1O)[C@]2(C)[C@]35CO5

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 502.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Liu Y, Gao X, Deeb D, Zhang Y, Shaw J, Valeriote FA, Gautam SC. Mycotoxin verrucarin A inhibits proliferation and induces apoptosis in prostate cancer cells by inhibiting prosurvival Akt/NF-kB/mTOR signaling. J Exp Ther Oncol. 2016 Nov;11(4):251-260. PubMed PMID: 27849335.

2: Bae EY, Lee SW, Seong S, Cho W, Ahn JS, Cho HS. Inhibitory Effects of Verrucarin A on Tunicamycin-Induced ER Stress in FaO Rat Liver Cells. Molecules. 2015 May 19;20(5):8988-96. doi: 10.3390/molecules20058988. PubMed PMID: 25996208.

3: Liu J, Simmons SO, Pei R. Regulation of IL-8 promoter activity by verrucarin A in human monocytic THP-1 cells. J Toxicol Environ Health A. 2014;77(19):1125-40. doi: 10.1080/15287394.2013.874246. PubMed PMID: 25119735.

4: Palanivel K, Kanimozhi V, Kadalmani B. 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 Oct;35(10):10159-67. doi: 10.1007/s13277-014-2286-1. Epub 2014 Jul 16. PubMed PMID: 25027398.

5: Palanivel K, Kanimozhi V, Kadalmani B, Akbarsha MA. Verrucarin A induces apoptosis through ROS-mediated EGFR/MAPK/Akt signaling pathways in MDA-MB-231 breast cancer cells. J Cell Biochem. 2014 Nov;115(11):2022-32. doi: 10.1002/jcb.24874. PubMed PMID: 24963595.

6: Yan F, Yu Y, Chow DC, Palzkill T, Madoux F, Hodder P, Chase P, Griffin PR, O'Malley BW, Lonard DM. Identification of verrucarin a as a potent and selective steroid receptor coactivator-3 small molecule inhibitor. PLoS One. 2014 Apr 17;9(4):e95243. doi: 10.1371/journal.pone.0095243. eCollection 2014. PubMed PMID: 24743578; PubMed Central PMCID: PMC3990629.

7: Jayasooriya RG, Moon DO, Park SR, Choi YH, Asami Y, Kim MO, Jang JH, Kim BY, Ahn JS, Kim GY. Combined treatment with verrucarin A and tumor necrosis factor-α sensitizes apoptosis by overexpression of nuclear factor-kappaB-mediated Fas. Environ Toxicol Pharmacol. 2013 Sep;36(2):303-10. doi: 10.1016/j.etap.2013.04.008. Epub 2013 Apr 25. PubMed PMID: 23708311.

8: Palanivel K, Kanimozhi V, Kadalmani B, Akbarsha MA. Verrucarin A, a protein synthesis inhibitor, induces growth inhibition and apoptosis in breast cancer cell lines MDA-MB-231 and T47D. Biotechnol Lett. 2013 Sep;35(9):1395-403. doi: 10.1007/s10529-013-1238-y. Epub 2013 May 21. PubMed PMID: 23690045.

9: Jayasooriya RG, Moon DO, Yun SG, Choi YH, Asami Y, Kim MO, Jang JH, Kim BY, Ahn JS, Kim GY. Verrucarin A enhances TRAIL-induced apoptosis via NF-κB-mediated Fas overexpression. Food Chem Toxicol. 2013 May;55:1-7. doi: 10.1016/j.fct.2012.12.045. Epub 2013 Jan 7. PubMed PMID: 23306790.

10: Moon DO, Asami Y, Long H, Jang JH, Bae EY, Kim BY, Choi YH, Kang CH, Ahn JS, Kim GY. Verrucarin A sensitizes TRAIL-induced apoptosis via the upregulation of DR5 in an eIF2α/CHOP-dependent manner. Toxicol In Vitro. 2013 Feb;27(1):257-63. doi: 10.1016/j.tiv.2012.09.001. Epub 2012 Sep 12. PubMed PMID: 22982206.

11: Woldemichael GM, Turbyville TJ, Vasselli JR, Linehan WM, McMahon JB. Lack of a functional VHL gene product sensitizes renal cell carcinoma cells to the apoptotic effects of the protein synthesis inhibitor verrucarin A. Neoplasia. 2012 Aug;14(8):771-7. PubMed PMID: 22952429; PubMed Central PMCID: PMC3431183.