Calactin

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

MedKoo CAT#: 584003

CAS#: 20304-47-6

Description: Calactin comes from the roots of the Asclepias curassavica L. and has anticancer properties from inducing apoptosis through an ERK signaling pathway.


Chemical Structure

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Calactin
CAS# 20304-47-6

Theoretical Analysis

MedKoo Cat#: 584003
Name: Calactin
CAS#: 20304-47-6
Chemical Formula: C29H40O10
Exact Mass: 548.2621
Molecular Weight: 548.629
Elemental Analysis: C, 63.49; H, 7.35; O, 29.16

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Calactin; Pecilocerin B; Pekilocerin B; Poekilocerin B; Pokilocerin B

IUPAC/Chemical Name: Card-20(22)-enolide, 3-((4,6-dideoxy-beta-D-erythro-hexopyranos-2-ulos-1-yl)oxy)-2,14-dihydroxy-19-oxo-, (2alpha,3beta,5alpha)-

InChi Key: WLEPWZGEVXFKPT-FFLRHQAWSA-N

InChi Code: InChI=1S/C29H40O10/c1-15-9-21(31)25(34)29(36,38-15)39-23-11-17-3-4-20-19(27(17,14-30)12-22(23)32)5-7-26(2)18(6-8-28(20,26)35)16-10-24(33)37-13-16/h10,14-15,17-23,31-32,35-36H,3-9,11-13H2,1-2H3/t15-,17+,18-,19+,20-,21+,22-,23-,26-,27-,28+,29+/m1/s1

SMILES Code: O=C1OCC([C@H]2CC[C@]3(O)[C@]4([H])CC[C@@]5([H])C[C@@H](O[C@@](O[C@@H](C6)C)(C([C@H]6O)=O)O)[C@H](O)C[C@]5(C=O)[C@@]4([H])CC[C@]23C)=C1

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 548.629 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: Lee CC, Lin YH, Chang WH, Wu YC, Chang JG. The small molecule calactin induces DNA damage and apoptosis in human leukemia cells. Eur J Cancer Prev. 2012 Sep;21(5):467-73. PubMed PMID: 22828439.

2: Parsons JA, Summers RJ. Cat assay for the emetic action of digitalis and related glycosides (digitoxin, digoxin, lanatoside C, ouabain and calactin). Br J Pharmacol. 1971 May;42(1):143-52. PubMed PMID: 5580699; PubMed Central PMCID: PMC1666988.

3: Liu J, Bai LP, Yang F, Yao X, Lei K, Kei Lam CW, Wu Q, Zhuang Y, Xiao R, Liao K, Kuok H, Li T, Liu L. Potent Antagonists of RORγt, Cardenolides from Calotropis gigantea, Exhibit Discrepant Effects on the Differentiation of T Lymphocyte Subsets. Mol Pharm. 2019 Feb 4;16(2):798-807. doi: 10.1021/acs.molpharmaceut.8b01063. Epub 2019 Jan 22. PubMed PMID: 30592425.

4: Mebs D, Wunder C, Toennes SW. Poor sequestration of toxic host plant cardenolides and their rapid loss in the milkweed butterfly Danaus chrysippus (Lepidoptera: Nymphalidae: Danainae: Danaini). Toxicon. 2017 Jun 1;131:1-5. doi: 10.1016/j.toxicon.2017.03.006. Epub 2017 Mar 9. PubMed PMID: 28284846.

5: Mutlib AE, Cheung HT, Watson TR. In vitro metabolism of the cardiotonic steroids gomphogenin and calactin. J Steroid Biochem. 1988 Jan;29(1):135-43. PubMed PMID: 3347047.

6: Groeneveld HW, Steijl H, Van Den Berg B, Elings JC. Rapid, quantitative HPLC analysis ofAsclepias fruticosa L. andDanaus plexippus L. cardenolides. J Chem Ecol. 1990 Dec;16(12):3373-82. doi: 10.1007/BF00982104. PubMed PMID: 24263435.

7: Mohamed NH, Liu M, Abdel-Mageed WM, Alwahibi LH, Dai H, Ismail MA, Badr G, Quinn RJ, Liu X, Zhang L, Shoreit AA. Cytotoxic cardenolides from the latex of Calotropis procera. Bioorg Med Chem Lett. 2015 Oct 15;25(20):4615-20. doi: 10.1016/j.bmcl.2015.08.044. Epub 2015 Aug 21. PubMed PMID: 26323871.

8: Züst T, Petschenka G, Hastings AP, Agrawal AA. Toxicity of Milkweed Leaves and Latex: Chromatographic Quantification Versus Biological Activity of Cardenolides in 16 Asclepias Species. J Chem Ecol. 2019 Jan;45(1):50-60. doi: 10.1007/s10886-018-1040-3. Epub 2018 Dec 7. PubMed PMID: 30523520.

9: Hamed AI, Plaza A, Balestrieri ML, Mahalel UA, Springuel IV, Oleszek W, Pizza C, Piacente S. Cardenolide glycosides from Pergularia tomentosa and their proapoptotic activity in Kaposi's sarcoma cells. J Nat Prod. 2006 Sep;69(9):1319-22. PubMed PMID: 16989527.

10: Brower LP, Seiber JN, Nelson CJ, Lynch SP, Hoggard MP, Cohen JA. Plant-determined variation in cardenolide content and thin-layer chromatography profiles of monarch butterflies,Danaus plexippus reared on milkweed plants in California : 3. Asclepias californica. J Chem Ecol. 1984 Dec;10(12):1823-57. doi: 10.1007/BF00987364. PubMed PMID: 24318436.

11: Mutlib AE, Cheung HT, Watson TR. In vivo and in vitro metabolism of gomphoside, a cardiotonic steroid with doubly-linked sugar. J Steroid Biochem. 1987 Jul;28(1):65-75. PubMed PMID: 3613576.

12: Lynch SP, Martin RA. Cardenolide content and thin-layer chromatography profiles of monarch butterflies,danaus plexippus L., and their larval host-plant milkweed,asclepias viridis walt., in northwestern louisiana. J Chem Ecol. 1987 Jan;13(1):47-70. doi: 10.1007/BF01020351. PubMed PMID: 24301359.