Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

I0661

Sigma-Aldrich

(−)-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

Sign Into View Organizational & Contract Pricing

Select a Size

1 MG
$438.00

$438.00

Please contact Customer Service for Availability
Request a Bulk Order
All Photos(1)

Select a Size

Change View
1 MG
$438.00

About This Item

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

$438.00

Please contact Customer Service for Availability
Request a Bulk Order

Quality Level

100

Assay

≥96% (HPLC)

form

powder

color

white

storage temp.

−20°C

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

InChI key

LUZOFMGZMUZSSK-LRDDRELGSA-N

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.[1] It serves as a precursor to the teleocidin class which are alkaloids.[2] It is a the pharmacophore of lyngbyatoxin[1] and teleocidins.[2]

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000388951
0000382449
0000382449
0000388951
0000130523

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Zhengren Xu et al.
Organic & biomolecular chemistry, 9(7), 2512-2517 (2011-02-23)
The total synthesis of protein kinase C activator (-)-indolactam V (IL-V) has been successfully completed with two separate approaches: From known 4-nitrotryptophan derivative 3 in 8 steps (49% overall yield) and from L-glutamic acid in 12 steps (18% overall yield)
Kazuhiro Irie et al.
Chemical record (New York, N.Y.), 5(4), 185-195 (2005-07-26)
Tumor promoters such as phorbol esters bind strongly to protein kinase C (PKC) isozymes to induce their activation. Since each PKC isozyme is involved in diverse biological events in addition to tumor promotion, the isozymes serve as promising therapeutic targets.
Synthesis of (-)-Epi-Indolactam V by an Intramolecular Buchwald-Hartwig C-N Coupling Cyclization Reaction
Mari M, et al.
The Journal of Organic Chemistry, 78(15), 7727-7734 (2013)
Minh U Huynh et al.
Journal of natural products, 73(1), 71-74 (2009-12-17)
The P450 cytochrome monooxygenase gene, ltxB, was cloned and overexpressed in Escherichia coli as a 6xHis-tagged protein. The resulting recombinant LtxB was purified by Ni-NTA affinity chromatography and characterized biochemically. Purified LtxB demonstrated typical cytochrome P450 spectroscopic properties including substrate-induced
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
View All Related Papers

Articles

Protein Kinase C (PKC)

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

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service