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MedKoo Cat#: 562839 | Name: Indolactam V

Description:

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

Indolactam V is an activator of protein kinase C. It induces changes in muscarinic receptor functions.

Chemical Structure

Indolactam V
Indolactam V
CAS#90365-57-4

Theoretical Analysis

MedKoo Cat#: 562839

Name: Indolactam V

CAS#: 90365-57-4

Chemical Formula: C17H23N3O2

Exact Mass: 301.1790

Molecular Weight: 301.39

Elemental Analysis: C, 67.75; H, 7.69; N, 13.94; O, 10.62

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
Indolactam V; Indolactam-V; (-)-Indolactam V; (-)-ILV;
IUPAC/Chemical Name
(2S,5S)-1,2,4,5,6,8-Hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one
InChi Key
LUZOFMGZMUZSSK-LRDDRELGSA-N
InChi Code
InChI=1S/C17H23N3O2/c1-10(2)16-17(22)19-12(9-21)7-11-8-18-13-5-4-6-14(15(11)13)20(16)3/h4-6,8,10,12,16,18,21H,7,9H2,1-3H3,(H,19,22)/t12-,16-/m0/s1
SMILES Code
O=C(N[C@H](CO)C1)[C@H](C(C)C)N(C)C2=CC=CC3=C2C1=CN3
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 301.39 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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Nat Commun. 2016 Mar 8;7:10849. doi: 10.1038/ncomms10849. PubMed PMID: 26952246; PubMed Central PMCID: PMC4786772. 5: Glover KP, Chen Z, Markell LK, Han X. Synergistic Gene Expression Signature Observed in TK6 Cells upon Co-Exposure to UVC-Irradiation and Protein Kinase C-Activating Tumor Promoters. PLoS One. 2015 Oct 2;10(10):e0139850. doi: 10.1371/journal.pone.0139850. eCollection 2015. PubMed PMID: 26431317; PubMed Central PMCID: PMC4592187. 6: Raveh A, Schultz PJ, Aschermann L, Carpenter C, Tamayo-Castillo G, Cao S, Clardy J, Neubig RR, Sherman DH, Sjögren B. Identification of protein kinase C activation as a novel mechanism for RGS2 protein upregulation through phenotypic screening of natural product extracts. Mol Pharmacol. 2014 Oct;86(4):406-16. doi: 10.1124/mol.114.092403. Epub 2014 Aug 1. PubMed PMID: 25086086. 7: Nathel NF, Shah TK, Bronner SM, Garg NK. Total syntheses of indolactam alkaloids (-)-indolactam V, (-)-pendolmycin, (-)-lyngbyatoxin A, and (-)-teleocidin A-2. Chem Sci. 2014 Jun 1;5(6):2184-2190. PubMed PMID: 24839542; PubMed Central PMCID: PMC4019407. 8: Mari M, Bartoccini F, Piersanti G. Synthesis of (-)-epi-indolactam V by an intramolecular Buchwald-Hartwig C-N coupling cyclization reaction. J Org Chem. 2013 Aug 2;78(15):7727-34. doi: 10.1021/jo4013767. Epub 2013 Jul 25. PubMed PMID: 23845025. 9: Ongley SE, Bian X, Zhang Y, Chau R, Gerwick WH, Müller R, Neilan BA. High-titer heterologous production in E. coli of lyngbyatoxin, a protein kinase C activator from an uncultured marine cyanobacterium. ACS Chem Biol. 2013 Sep 20;8(9):1888-93. doi: 10.1021/cb400189j. Epub 2013 Jun 17. PubMed PMID: 23751865; PubMed Central PMCID: PMC3880125. 10: Pal D, Outram SP, Basu A. Novel regulation of protein kinase C-η. Biochem Biophys Res Commun. 2012 Sep 7;425(4):836-41. doi: 10.1016/j.bbrc.2012.07.163. Epub 2012 Aug 7. PubMed PMID: 22892130; PubMed Central PMCID: PMC3438288. 11: Naujok O, Lenzen S. A critical re-evaluation of CD24-positivity of human embryonic stem cells differentiated into pancreatic progenitors. Stem Cell Rev. 2012 Sep;8(3):779-91. doi: 10.1007/s12015-012-9362-y. PubMed PMID: 22529013. 12: Ohmine S, Squillace KA, Hartjes KA, Deeds MC, Armstrong AS, Thatava T, Sakuma T, Terzic A, Kudva Y, Ikeda Y. Reprogrammed keratinocytes from elderly type 2 diabetes patients suppress senescence genes to acquire induced pluripotency. Aging (Albany NY). 2012 Jan;4(1):60-73. PubMed PMID: 22308265; PubMed Central PMCID: PMC3292906. 13: Kedei N, Lubart E, Lewin NE, Telek A, Lim L, Mannan P, Garfield SH, Kraft MB, Keck GE, Kolusheva S, Jelinek R, Blumberg PM. Some phorbol esters might partially resemble bryostatin 1 in their actions on LNCaP prostate cancer cells and U937 leukemia cells. Chembiochem. 2011 May 16;12(8):1242-51. doi: 10.1002/cbic.201100064. Epub 2011 May 3. PubMed PMID: 21542090; PubMed Central PMCID: PMC3313843. 14: Bronner SM, Goetz AE, Garg NK. Overturning indolyne regioselectivities and synthesis of indolactam V. J Am Chem Soc. 2011 Mar 23;133(11):3832-5. doi: 10.1021/ja200437g. Epub 2011 Feb 25. PubMed PMID: 21351773; PubMed Central PMCID: PMC3060274. 15: Xu Z, Zhang F, Zhang L, Jia Y. Total synthesis of (-)-indolactam V. Org Biomol Chem. 2011 Apr 7;9(7):2512-7. doi: 10.1039/c0ob01115k. Epub 2011 Feb 21. PubMed PMID: 21340068. 16: Thatava T, Nelson TJ, Edukulla R, Sakuma T, Ohmine S, Tonne JM, Yamada S, Kudva Y, Terzic A, Ikeda Y. Indolactam V/GLP-1-mediated differentiation of human iPS cells into glucose-responsive insulin-secreting progeny. Gene Ther. 2011 Mar;18(3):283-93. doi: 10.1038/gt.2010.145. Epub 2010 Nov 4. PubMed PMID: 21048796; PubMed Central PMCID: PMC3060028. 17: Takahashi S, Takagi H, Toyoda A, Uramoto M, Nogawa T, Ueki M, Sakaki Y, Osada H. Biochemical characterization of a novel indole prenyltransferase from Streptomyces sp. SN-593. J Bacteriol. 2010 Jun;192(11):2839-51. doi: 10.1128/JB.01557-09. 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