Withangulatin A | CAS#120824-03-5 | SERCA antitumor agent

MedKoo Cat#: 463140 | Name: Withangulatin A

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Description:

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

Withangulatin A is a natural potent antitumor agent, targeting sarco/endoplasmic reticulum calcium-ATPase (SERCA).

Chemical Structure

Withangulatin A

CAS#120824-03-5

Theoretical Analysis

MedKoo Cat#: 463140

Name: Withangulatin A

CAS#: 120824-03-5

Chemical Formula: C30H38O8

Exact Mass: 526.2567

Molecular Weight: 526.63

Elemental Analysis: C, 68.42; H, 7.27; O, 24.30

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 1,250.00	2 Weeks
5mg	USD 2,950.00	2 Weeks

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Synonym

Withangulatin A; WithangulatinA; Withangulatin-A; Withagulatin A;

IUPAC/Chemical Name

(4S,4aR,5aR,6aR,6bR,7S,9aR,11aS,11bR)-9-((S)-1-((R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-4,6b-dihydroxy-9a,11b-dimethyl-1-oxo-1,4,5a,6,6a,6b,7,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-7-yl acetate

InChi Key

PLPXOWZTDPJPHC-ISIACCJKSA-N

InChi Code

InChI=1S/C30H38O8/c1-14-11-21(37-26(34)15(14)2)16(3)19-12-24(36-17(4)31)29(35)20-13-25-30(38-25)23(33)8-7-22(32)28(30,6)18(20)9-10-27(19,29)5/h7-8,12,16,18,20-21,23-25,33,35H,9-11,13H2,1-6H3/t16-,18-,20+,21+,23-,24-,25+,27+,28-,29-,30+/m0/s1

SMILES Code

CC(C[C@H]([C@@H](C)C1=C[C@H](OC(C)=O)[C@]2(O)[C@]1(C)CC[C@H]3[C@H]2C[C@@H](O4)[C@@]54[C@]3(C)C(C=C[C@@H]5O)=O)O6)=C(C)C6=O

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 526.63 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.

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

1: Wang C, Li S, Zhao J, Yang H, Yin F, Ding M, Luo J, Wang X, Kong L. Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment. J Med Chem. 2020 Oct 8;63(19):11195-11214. doi: 10.1021/acs.jmedchem.0c01128. Epub 2020 Sep 17. PMID: 32886510. 2: Zhu T, Chen C, Wang S, Zhang Y, Zhu D, Li L, Luo J, Kong L. Cellular target identification of Withangulatin A using fluorescent analogues and subsequent chemical proteomics. Chem Commun (Camb). 2019 Jul 11;55(57):8231-8234. doi: 10.1039/c9cc03653a. PMID: 31241075. 3: Sun L, Zhou L, Chen M, Zhong R, Liu J. Amelioration of systemic lupus erythematosus by Withangulatin A in MRL/lpr mice. J Cell Biochem. 2011 Sep;112(9):2376-82. doi: 10.1002/jcb.23160. PMID: 21520246. 4: Liu Q, Chen J, Wang X, Yu L, Hu LH, Shen X. Withagulatin A inhibits hepatic stellate cell viability and procollagen I production through Akt and Smad signaling pathways. Acta Pharmacol Sin. 2010 Aug;31(8):944-52. doi: 10.1038/aps.2010.72. Epub 2010 Jul 19. PMID: 20644552; PMCID: PMC4007817. 5: Sun L, Liu J, Cui D, Li J, Yu Y, Ma L, Hu L. Anti-inflammatory function of Withangulatin A by targeted inhibiting COX-2 expression via MAPK and NF-kappaB pathways. J Cell Biochem. 2010 Feb 15;109(3):532-41. doi: 10.1002/jcb.22430. PMID: 19950196. 6: Lee SW, Pan MH, Chen CM, Chen ZT. Withangulatin I, a new cytotoxic withanolide from Physalis angulata. Chem Pharm Bull (Tokyo). 2008 Feb;56(2):234-6. doi: 10.1248/cpb.56.234. PMID: 18239318. 7: Lee YC, Lai YK. Integrity of intermediate filaments is associated with the development of acquired thermotolerance in 9L rat brain tumor cells. J Cell Biochem. 1995 Jan;57(1):150-62. doi: 10.1002/jcb.240570115. PMID: 7721954. 8: Perng MD, Cheng TJ, Chen CM, Lai YK. Induction of aggregation and augmentation of protein kinase-mediated phosphorylation of purified vimentin intermediate filaments by withangulatin A. Mol Pharmacol. 1994 Oct;46(4):612-7. PMID: 7969040. 9: Lee WC, Lee YC, Perng MD, Chen CM, Lai YK. Induction of vimentin modification and vimentin-HSP72 association by withangulatin A in 9L rat brain tumor cells. J Cell Biochem. 1993 Jul;52(3):253-65. doi: 10.1002/jcb.240520302. PMID: 8366140. 10: Lai YK, Shen CH, Cheng TJ, Hou MC, Lee WC. Enhanced phosphorylation of a 65 kDa protein is associated with rapid induction of stress proteins in 9L rat brain tumor cells. J Cell Biochem. 1993 Mar;51(3):369-79. doi: 10.1002/jcb.240510317. PMID: 8501139. 11: Lee WC, Lin KY, Chen CM, Chen ZT, Liu HJ, Lai YK. Induction of heat-shock response and alterations of protein phosphorylation by a novel topoisomerase II inhibitor, withangulatin A, in 9L rat brain tumor cells. J Cell Physiol. 1991 Oct;149(1):66-76. doi: 10.1002/jcp.1041490110. PMID: 1658010. 12: Juang JK, Huang HW, Chen CM, Liu HJ. A new compound, withangulatin A, promotes type II DNA topoisomerase-mediated DNA damage. Biochem Biophys Res Commun. 1989 Mar 31;159(3):1128-34. doi: 10.1016/0006-291x(89)92226-2. PMID: 2539141.