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MedKoo Cat#: 465321 | Name: Caudatin
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Description:

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

Caudatin is a C-21 steroid that has been found in C. auriculatum and has anticancer activity. It is cytotoxic to SMMC-7721, MCF-7, and HeLa cells (IC50s = 24.95, 65.82, and 247.54 µM, respectively). Caudatin (50-300 µM) induces apoptosis in and inhibits mammosphere formation by MDA-MB-231 breast cancer cells, as well as decreases the number of cancer stem cells (CSCs) in the MDA-MB-231 cell population. In vivo, caudatin (10 mg/kg) reduces tumor volume in an MDA-MB-231 mouse xenograft model.

Chemical Structure

Caudatin
Caudatin
CAS#38395-02-7

Theoretical Analysis

MedKoo Cat#: 465321

Name: Caudatin

CAS#: 38395-02-7

Chemical Formula: C28H42O7

Exact Mass: 490.2931

Molecular Weight: 490.64

Elemental Analysis: C, 68.55; H, 8.63; O, 22.83

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 850.00 2 Weeks
10mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Caudatin;
IUPAC/Chemical Name
(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-3,8,14,17-tetrahydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-12-yl (E)-3,4-dimethylpent-2-enoate
InChi Key
VWLXIXALPNYWFH-UXGQNDOZSA-N
InChi Code
InChI=1S/C28H42O7/c1-16(2)17(3)13-23(31)35-22-15-21-24(5)9-8-20(30)14-19(24)7-10-27(21,33)28(34)12-11-26(32,18(4)29)25(22,28)6/h7,13,16,20-22,30,32-34H,8-12,14-15H2,1-6H3/b17-13+/t20-,21+,22+,24-,25+,26+,27-,28+/m0/s1
SMILES Code
C[C@@]12[C@@](CC[C@]2(C(C)=O)O)(O)[C@@]3(O)[C@]([H])(C[C@H]1OC(/C=C(C(C)C)\C)=O)[C@]4(C)C(C[C@@H](O)CC4)=CC3
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Solvent mg/mL mM
Solubility
DMF 30.0 61.15
DMSO 30.0 61.15
Ethanol 30.0 61.15
Ethanol:PBS (pH 7.2) (1:7) 0.1 0.24
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 490.64 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
1: Bailly C. Anticancer properties of caudatin and related C-21 steroidal glycosides from Cynanchum plants. Steroids. 2021 Aug;172:108855. doi: 10.1016/j.steroids.2021.108855. Epub 2021 May 1. PMID: 33945800. 2: Xia Z, Zhang HX, Xu TQ, Chen YM, Zhou GX. [Chemical constituents from Xanthii Fructus]. Zhongguo Zhong Yao Za Zhi. 2020 Jun;45(12):2907-2915. Chinese. doi: 10.19540/j.cnki.cjcmm.20200228.201. PMID: 32627466. 3: Song J, Ding W, Liu B, Liu D, Xia Z, Zhang L, Cui L, Luo Y, Jia X, Feng L. Anticancer effect of caudatin in diethylnitrosamine‑induced hepatocarcinogenesis in rats. Mol Med Rep. 2020 Aug;22(2):697-706. doi: 10.3892/mmr.2020.11135. Epub 2020 May 7. PMID: 32626931; PMCID: PMC7339819. 4: Zhen X, Choi HS, Kim JH, Kim SL, Liu R, Ko YC, Yun BS, Lee DS. Caudatin Isolated from Cynanchum auriculatum Inhibits Breast Cancer Stem Cell Formation via a GR/YAP Signaling. Biomolecules. 2020 Jun 18;10(6):925. doi: 10.3390/biom10060925. PMID: 32570844; PMCID: PMC7355644. 5: Chen WH, Zhang ZZ, Ban YF, Rahman K, Ye BZ, Sun XL, Tan HY, Zheng XH, Liu HY, Xu LC, Yan B, Han T. Cynanchum bungei Decne and its two related species for "Baishouwu": A review on traditional uses, phytochemistry, and pharmacological activities. J Ethnopharmacol. 2019 Oct 28;243:112110. doi: 10.1016/j.jep.2019.112110. Epub 2019 Jul 24. PMID: 31351190. 6: Fei HR, Yuan C, Wang GL, Zhao Y, Li ZJ, Du X, Wang FZ. Caudatin potentiates the anti-tumor effects of TRAIL against human breast cancer by upregulating DR5. Phytomedicine. 2019 Sep;62:152950. doi: 10.1016/j.phymed.2019.152950. Epub 2019 May 6. PMID: 31102888. 7: Wang X, Fu X, Zhao S, Fu X, Zhang H, Shao L, Li G, Fan C. Antiangiogenic properties of caudatin in vitro and in vivo by suppression of VEGF‑VEGFR2‑AKT/FAK signal axis. Mol Med Rep. 2017 Dec;16(6):8937-8943. doi: 10.3892/mmr.2017.7730. Epub 2017 Oct 5. PMID: 28990104; PMCID: PMC5779977. 8: Tan ZW, Xie S, Hu SY, Liao T, Liu P, Peng KH, Yang XZ, He ZL, Tang HY, Cui Y, Peng XN, Zhang J, Zhou C. Caudatin targets TNFAIP1/NF-κB and cytochrome c/caspase signaling to suppress tumor progression in human uterine cancer. Int J Oncol. 2016 Oct;49(4):1638-1650. doi: 10.3892/ijo.2016.3662. Epub 2016 Aug 19. PMID: 27633631. 9: Zhu LZ, Hou YJ, Zhao M, Yang MF, Fu XT, Sun JY, Fu XY, Shao LR, Zhang HF, Fan CD, Gao HL, Sun BL. Caudatin induces caspase-dependent apoptosis in human glioma cells with involvement of mitochondrial dysfunction and reactive oxygen species generation. Cell Biol Toxicol. 2016 Aug;32(4):333-45. doi: 10.1007/s10565-016-9338-9. Epub 2016 May 16. PMID: 27184666. 10: Huang LJ, Wang B, Zhang JX, Yuan CM, Gu W, Mu SZ, Hao XJ. Synthesis and evaluation of antifungal activity of C21-steroidal derivatives. Bioorg Med Chem Lett. 2016 Apr 15;26(8):2040-3. doi: 10.1016/j.bmcl.2016.02.080. Epub 2016 Feb 27. PMID: 26947608. 11: Li X, Luo Y, Li GP, Yang QX. Pregnane glycosides from the antidepressant active fraction of cultivated Cynanchum otophyllum. Fitoterapia. 2016 Apr;110:96-102. doi: 10.1016/j.fitote.2016.02.014. Epub 2016 Mar 2. PMID: 26944766. 12: Chen XL, Geng CA, Chen JJ. A Fragmentation Study of Six C21 Steroidal Aglycones by Electrospray Ionization Ion-Trap Time-of-Flight Tandem Mass Spectrometry. Nat Prod Commun. 2015 Dec;10(12):2053-8. PMID: 26882663. 13: Zan K, Guo LN, Zheng J, Ma SC. [Chemical constituents of ethnic medicine Cynanchum otophyllum]. Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(1):101-105. Chinese. doi: 10.4268/cjcmm20160120. PMID: 28845649. 14: Zhang M, Li X, Xiang C, Qin Y, He J, Li BC, Li P. Cytotoxicity of pregnane glycosides of Cynanchum otophyllum. Steroids. 2015 Dec;104:49-60. doi: 10.1016/j.steroids.2015.08.010. Epub 2015 Aug 20. PMID: 26297951. 15: Zhu Q, Hu Y, Shan Y, Wang Y, Wu X, Mao B, Ge RS. Determination of Caudatin in Rat Plasma by UPLC-MS/MS: Application to a Preclinical Pharmacokinetic Study. Pharmacology. 2015;96(1-2):49-54. doi: 10.1159/000381784. Epub 2015 Jun 12. PMID: 26088709. 16: Zhang W, Peng YR, Ding YF. Biotransformation and metabolic profile of caudatin-2,6-dideoxy-3-O-methy-β-d-cymaropyranoside with human intestinal microflora by liquid chromatography quadrupole time-of-flight mass spectrometry. Biomed Chromatogr. 2015 Nov;29(11):1715-23. doi: 10.1002/bmc.3484. Epub 2015 May 27. PMID: 26018801. 17: Tao X, Ma Y, Chen J, Zhao H. Design, synthesis and biological evaluation of caudatin and its ester derivatives as novel antitumor agents. Nat Prod Commun. 2015 Apr;10(4):571-4. PMID: 25973478. 18: Fu XY, Zhang S, Wang K, Yang MF, Fan CD, Sun BL. Caudatin Inhibits Human Glioma Cells Growth Through Triggering DNA Damage-Mediated Cell Cycle Arrest. Cell Mol Neurobiol. 2015 Oct;35(7):953-9. doi: 10.1007/s10571-015-0190-x. Epub 2015 Apr 10. PMID: 25860846. 19: Peng Y, Ding Y. Pharmacokinetics and tissue distribution study of caudatin in normal and diethylnitrosamine-induced hepatocellular carcinoma model rats. Molecules. 2015 Mar 5;20(3):4225-37. doi: 10.3390/molecules20034225. PMID: 25751784; PMCID: PMC6272519. 20: Li X, Zhang M, Xiang C, Li BC, Li P. Antiepileptic C21 steroids from the roots of Cynanchum otophyllum. J Asian Nat Prod Res. 2015;17(7):724-32. doi: 10.1080/10286020.2014.1001380. Epub 2015 Jan 12. PMID: 25579837.

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