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I0661

Sigma-Aldrich

(−)-Indolactam V

≥96% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C17H23N3O2
Numéro CAS:
90365-57-4
Poids moléculaire :
301.38
Numéro MDL:
MFCD00151197
Code UNSPSC :
12352200
ID de substance PubChem :
329815323
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥96% (HPLC)

Forme

powder

Couleur

white

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

LUZOFMGZMUZSSK-LRDDRELGSA-N

Actions biochimiques/physiologiques

(-)-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.

Caractéristiques et avantages

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
Kazuhiro Irie et al.
Bioorganic & medicinal chemistry, 12(17), 4575-4583 (2004-09-11)
Recent investigations discovered nonkinase-type phorbol ester receptors, RasGRPs, chimaerins, and Unc13s. Phorbol ester binding occurs at the cysteine-rich sequences of about 50 residues in the C1 domains of these receptors. Fifty-one-residue RasGRP C1 peptides except for RasGRP2 showed significant phorbol
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
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
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
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