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Merck
CN

I0661

(−)-Indolactam V

≥96% (HPLC)

Synonym(s):

(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

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About This Item

Empirical Formula (Hill Notation):
C17H23N3O2
CAS Number:
90365-57-4
Molecular Weight:
301.38
NACRES:
NA.77
PubChem Substance ID:
329815323
UNSPSC Code:
12352200
MDL number:
MFCD00151197

Key Documents

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InChI key

LUZOFMGZMUZSSK-LRDDRELGSA-N

SMILES string

CC(C)[C@@H]1N(C)c2cccc3[nH]cc(C[C@@H](CO)NC1=O)c23

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

assay

≥96% (HPLC)

form

powder

color

white

storage temp.

−20°C

Quality Level

100

Biochem/physiol Actions

(-)-Indolactam V is a PKC activator shown to effect differentiation in embryonic stem cells leading to development of pancreatic precursors.
(-)-Indolactam V is a PKC activator shown to effect differentiation in embryonic stem cells leading to development of pancreatic precursors. It is active in the mouse model.
(−)-Indolactam V is naturally present in Streptoverticillium blastmyceticum. It serves as a precursor to the teleocidin class which are alkaloids. It is a the pharmacophore of lyngbyatoxin and teleocidins.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000388951
0000382449
0000382449
0000388951
0000130523

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Yu Nakagawa et al.
Journal of the American Chemical Society, 127(16), 5746-5747 (2005-04-21)
The CH/pi interaction between the indole ring of indolactam-V (IL-V) and the hydrogen atom at position 4 of Pro-11 of the PKCdelta C1B domain was evaluated using the mutant peptide of the PKCdelta C1B domain, in which the CH/pi interaction
Ryo C Yanagita et al.
Journal of medicinal chemistry, 51(1), 46-56 (2007-12-13)
Conventional and novel protein kinase C (PKC) isozymes are the main targets of tumor promoters. We developed 1-hexylindolactam-V10 ( 5) as a selective activator for novel PKC isozymes that play important roles in various cellular processes related to tumor promotion
Judith J Eckert et al.
Reproduction (Cambridge, England), 127(6), 653-667 (2004-06-04)
Epithelial differentiation including tight junction (TJ) formation occurs exclusively within the trophectoderm (TE) lineage of the mouse blastocyst. Here we examine mechanisms by which TJ protein membrane assembly might be regulated by protein kinase C (PKC) in the embryo. To
Daniel J Edwards et al.
Journal of the American Chemical Society, 126(37), 11432-11433 (2004-09-16)
The lyngbyatoxins are potent skin irritants produced by Lyngbya majuscula and cause a condition known as "Swimmer's Itch" off Honolulu, HI. Reported is the molecular cloning of the lyngbyatoxin (ltx) biosynthetic gene cluster from L. majuscula using a strategy based
Akiko Masuda et al.
Bioscience, biotechnology, and biochemistry, 66(7), 1615-1617 (2002-09-13)
Two conformationally restricted analogues of (-)-indolactam-V (1) (cis and trans amides) were examined for their binding selectivity to the synthetic C1 peptides of all protein kinase C (PKC) isozymes. Although the binding constants of the cis amide-restricted analogue (2) were
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Articles

Protein Kinase C (PKC)

Protein kinase C (PKC) is an AGC kinase that phosphorylates serine and threonine residues in many target proteins.

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