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MedKoo Cat#: 596215 | Name: Jervine HCl

Description:

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

Jervine (11-Ketocyclopamine) is a naturally occuring steroidal alkaloid, and is derived from the Veratrum plant species. Jervine is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation. Over the Hedgehog signaling pathway Jervine effectively inhibit the tumor growth using three human tumor xenograft models including lung cancer, pancreatic cancer and basal cell carcinoma. Jervine has the potential to advance to a treatment for different tumors.

Chemical Structure

Jervine HCl
Jervine HCl
CAS#60326-37-6

Theoretical Analysis

MedKoo Cat#: 596215

Name: Jervine HCl

CAS#: 60326-37-6

Chemical Formula: C27H40ClNO3

Exact Mass: 461.2697

Molecular Weight: 462.07

Elemental Analysis: C, 70.18; H, 8.73; Cl, 7.67; N, 3.03; O, 10.39

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Jervine HCl; Jervine hydrochloride;
IUPAC/Chemical Name
(3S,3'R,3a'S,6aS,6bS,6'S,7a'R,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11a,11b-hexadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-11(1H)-one hydrochloride
InChi Key
BTHSHLDGBOARGK-AVEQMEPMSA-N
InChi Code
InChI=1S/C27H39NO3.ClH/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2;/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3;1H/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-;/m0./s1
SMILES Code
O=C1[C@]2([H])[C@]3(C)C(C[C@@H](O)CC3)=CC[C@@]2([H])[C@]4([H])CC[C@]5(O[C@@]6([H])[C@@]([C@H]5C)([H])NC[C@@H](C)C6)C(C)=C41.[H]Cl
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 462.07 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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J Ethnopharmacol. 2016 Feb 17;179:274-9. doi: 10.1016/j.jep.2015.12.059. Epub 2015 Dec 29. PubMed PMID: 26743225. 4: Wang L, Yao ZP, Li P, Chen SB, So PK, Shi ZQ, Hu B, Liu LF, Xin GZ. Global detection and semi-quantification of Fritillaria alkaloids in Fritillariae Ussuriensis Bulbus by a non-targeted multiple reaction monitoring approach. J Sep Sci. 2016 Jan;39(2):287-95. doi: 10.1002/jssc.201500880. Epub 2015 Dec 7. PubMed PMID: 26530331. 5: Torii D, Soeno Y, Fujita K, Sato K, Aoba T, Taya Y. Embryonic tongue morphogenesis in an organ culture model of mouse mandibular arches: blocking Sonic hedgehog signaling leads to microglossia. In Vitro Cell Dev Biol Anim. 2016 Jan;52(1):89-99. doi: 10.1007/s11626-015-9951-6. Epub 2015 Sep 3. PubMed PMID: 26334330. 6: Noguchi KK, Cabrera OH, Swiney BS, Salinas-Contreras P, Smith JK, Farber NB. Hedgehog regulates cerebellar progenitor cell and medulloblastoma apoptosis. Neurobiol Dis. 2015 Nov;83:35-43. doi: 10.1016/j.nbd.2015.08.020. Epub 2015 Aug 28. PubMed PMID: 26319366; PubMed Central PMCID: PMC4674325. 7: Kang C, Han JH, Oh J, Kulkarni R, Zhou W, Ferreira D, Jang TS, Myung CS, Na M. Steroidal Alkaloids from Veratrum nigrum Enhance Glucose Uptake in Skeletal Muscle Cells. J Nat Prod. 2015 Apr 24;78(4):803-10. doi: 10.1021/np501049g. Epub 2015 Apr 2. PubMed PMID: 25835537. 8: Carlier J, Guitton J, Romeuf L, Bévalot F, Boyer B, Fanton L, Gaillard Y. Screening approach by ultra-high performance liquid chromatography-tandem mass spectrometry for the blood quantification of thirty-four toxic principles of plant origin. Application to forensic toxicology. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 15;975:65-76. doi: 10.1016/j.jchromb.2014.10.028. Epub 2014 Nov 1. PubMed PMID: 25438245. 9: Aydin T, Cakir A, Kazaz C, Bayrak N, Bayir Y, Taşkesenligil Y. Insecticidal metabolites from the rhizomes of Veratrum album against adults of Colorado potato beetle, Leptinotarsa decemlineata. Chem Biodivers. 2014 Aug;11(8):1192-204. doi: 10.1002/cbdv.201300407. PubMed PMID: 25146763. 10: Kazuma K, Konno K. [Poisoning by accidental ingestion of poisonous plants]. Chudoku Kenkyu. 2013 Jun;26(2):97-101. Review. Japanese. PubMed PMID: 23855239. 11: Ghezali L, Leger DY, Limami Y, Cook-Moreau J, Beneytout JL, Liagre B. Cyclopamine and jervine induce COX-2 overexpression in human erythroleukemia cells but only cyclopamine has a pro-apoptotic effect. Exp Cell Res. 2013 Apr 15;319(7):1043-53. doi: 10.1016/j.yexcr.2013.01.014. Epub 2013 Jan 25. PubMed PMID: 23357584. 12: Balbuena J, Pachon G, Lopez-Torrents G, Aran JM, Castresana JS, Petriz J. ABCG2 is required to control the sonic hedgehog pathway in side population cells with stem-like properties. Cytometry A. 2011 Sep;79(9):672-83. doi: 10.1002/cyto.a.21103. Epub 2011 Jul 19. PubMed PMID: 21774076. 13: Zhou JL, Xin GZ, Shi ZQ, Ren MT, Qi LW, Li HJ, Li P. Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Chromatogr A. 2010 Nov 5;1217(45):7109-22. doi: 10.1016/j.chroma.2010.09.019. Epub 2010 Sep 16. PubMed PMID: 20926090. 14: Bechtel LK, Lawrence DT, Haverstick D, Powers JS, Wyatt SA, Croley T, Holstege CP. Ingestion of false hellebore plants can cross-react with a digoxin clinical chemistry assay. Clin Toxicol (Phila). 2010 Jun;48(5):435-42. doi: 10.3109/15563651003733666. PubMed PMID: 20586573. 15: Tang J, Li HL, Shen YH, Jin HZ, Yan SK, Liu XH, Zeng HW, Liu RH, Tan YX, Zhang WD. Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum. Phytother Res. 2010 Jun;24(6):821-6. doi: 10.1002/ptr.3022. PubMed PMID: 20013819. 16: Heretsch P, Rabe S, Giannis A. Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine. Org Lett. 2009 Dec 3;11(23):5410-2. doi: 10.1021/ol902270f. PubMed PMID: 19883099. 17: Wilson CW, Chen MH, Chuang PT. Smoothened adopts multiple active and inactive conformations capable of trafficking to the primary cilium. PLoS One. 2009;4(4):e5182. doi: 10.1371/journal.pone.0005182. Epub 2009 Apr 13. PubMed PMID: 19365551; PubMed Central PMCID: PMC2664476. 18: Grobosch T, Binscheck T, Martens F, Lampe D. Accidental intoxication with Veratrum album. J Anal Toxicol. 2008 Nov-Dec;32(9):768-73. PubMed PMID: 19021933. 19: Cong Y, Wang JH, Wang R, Zeng YM, Liu CD, Li X. A study on the chemical constituents of Veratrum nigrum L. processed by rice vinegar. J Asian Nat Prod Res. 2008 Jul-Aug;10(7-8):619-24. doi: 10.1080/10286020802133266. PubMed PMID: 18636372. 20: Tang J, Li HL, Shen YH, Jin HZ, Yan SK, Liu RH, Zhang WD. Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum. Phytother Res. 2008 Aug;22(8):1093-6. doi: 10.1002/ptr.2463. PubMed PMID: 18570211.