Bisindolylmaleimide III - ≥98% , CAS No.137592-43-9

CAS: 137592-43-9 Cat. No.: B276080 Molecular Weight: 384.43 Beilstein Registry Number: 10489041

GRADE & PURITY ≥98%

Synonyms

3-[1-(3-Aminopropyl)indol-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

3-[1-(3-Aminopropyl)indol-3-yl]-4-(1H-indol-3-yl)pyrrole-2, 5-dione

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Potent PKC inhibitor (IC 50 = 26 nM, PKCα). Inhibits S6K1, MAPKAP-K1, RSK2 and MSK1 with similar potency. Inhibits GSK3β. Inhibits PDK1. Does not show TNFα-dependent apoptotic effects like Bisindolylmaleimide X.

Source

Synthetic

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Product Properties

• pKa: pKₐ: 8.15 (Predicted), pKₐ: 10.24 (Predicted)

Names and Identifiers

• Pubchem Sid: 504750564
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750564
• Canonical Smiles: C1=CC=C2C(=C1)C(=CN2)C3=C(C(=O)NC3=O)C4=CN(C5=CC=CC=C54)CCCN
• IUPAC Name: 3-[1-(3-aminopropyl)indol-3-yl]-4-(1H-indol-3-yl)pyrrole-2,5-dione
• InChIKey: APYXQTXFRIDSGE-UHFFFAOYSA-N
• INCHI: 1S/C23H20N4O2/c24-10-5-11-27-13-17(15-7-2-4-9-19(15)27)21-20(22(28)26-23(21)29)16-12-25-18-8-3-1-6-14(16)18/h1-4,6-9,12-13,25H,5,10-11,24H2,(H,26,28,29)
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C3=C(C(=O)NC3=O)C4=CN(C5=CC=CC=C54)CCCN
• Molecular Weight: 384.43
• Beilstein: 10489041
• Reaxy-Rn: 10489041
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10489041&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass N-alkylindoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: N-alkylindoles
• Intermediate Tree Nodes: Not available
• Direct Parent: N-alkylindoles
• Alternative Parents: Indoles Maleimides Substituted pyrroles Benzenoids Pyrrolines N-unsubstituted carboxylic acid imides Heteroaromatic compounds Dicarboximides Amino acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-alkylindole - Indole - Maleimide - Substituted pyrrole - Benzenoid - Carboxylic acid imide - Dicarboximide - Carboxylic acid imide, n-unsubstituted - Pyrrole - Pyrroline - Heteroaromatic compound - Amino acid or derivatives - Carboxylic acid derivative - Azacycle - Carbonyl group - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Amine - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
• External Descriptors: indoles - maleimides

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MAPK11 Tchem MAP kinase p38 beta (2785 Activities)

Discover Target: MAPK11

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

Discover Target: LCK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)

Discover Target: MAPK14

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

Discover Target: GSK3B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RPS6KA5 Tchem Ribosomal protein S6 kinase alpha 5 (3355 Activities)

Discover Target: RPS6KA5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK13 Tchem MAP kinase p38 delta (2605 Activities)

Discover Target: MAPK13

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPKAPK2 Tchem MAP kinase-activated protein kinase 2 (4814 Activities)

Discover Target: MAPKAPK2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPKAPK5 Tchem MAP kinase-activated protein kinase 5 (2831 Activities)

Discover Target: MAPKAPK5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ROCK2 Tclin Rho-associated protein kinase 2 (6206 Activities)

Discover Target: ROCK2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAMK2D Tchem CaM kinase II delta (2813 Activities)

Discover Target: CAMK2D

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRKCA Tchem Protein kinase C alpha (5923 Activities)

Discover Target: PRKCA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK8 Tchem c-Jun N-terminal kinase 1 (5038 Activities)

Discover Target: MAPK8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)

Discover Target: AKT1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PDK1 Tchem Pyruvate dehydrogenase kinase isoform 1 (2021 Activities)

Discover Target: PDK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SGK1 Tchem Serine/threonine-protein kinase Sgk1 (2343 Activities)

Discover Target: SGK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RPS6KB1 Tchem Ribosomal protein S6 kinase 1 (4456 Activities)

Discover Target: RPS6KB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHEK1 Tchem Serine/threonine-protein kinase Chk1 (6846 Activities)

Discover Target: CHEK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK12 Tchem MAP kinase p38 gamma (2776 Activities)

Discover Target: MAPK12

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol and in DMSO
• Refractive Index: n20D1.74 (Predicted)
• Boil Point(°C): 708.70° C at 760 mmHg (Predicted)
• Melt Point(°C): 326.33° C (Predicted)
• Molecular Weight: 384.400 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 384.159 Da
• Monoisotopic Mass: 384.159 Da
• Topological Polar Surface Area: 92.900 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 705.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1