Indirubin - analytical standard, ≥95% , CAS No.479-41-4

CAS: 479-41-4 Cat. No.: I111267 Summenformel: C₁₆H₁₀N₂O₂ Molekulargewicht: 262.26 EG-Nummer: 610-392-0

QUALITÄT & REINHEIT Analytical standard, ≥95%

Synonyms

(3Z)-3-(3-oxoindolin-2-ylidene)indolin-2-one|2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-, (3E)-|(3E)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one|(E)-[2,3'-biindolinylidene]-2',3-dione|BI164578|(3E)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one|Couroupitine B|Indirubin,(S)|Isoindirubine|INDARUBICIN|INDIRUBIN [WHO-DD]|Indigo Red|(delta2,3'-Biindoline)-2',3-dione|Isoindogotin|Indirubin derivative, 1|(Z)-[2,3'-biindolinylidene]-2',3-dione|(Z)-[2,3-Biindolinylidene]-2,3-dione|3-(1,3-dihydro-3-oxo-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-one|Isoindirubin|(delta(sup 2,3')-BIINDOLINE)-2',3-DIONE|3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one|(3Z)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one|Indirubin- Bio-X|[.DELTA.2,3-dione|2H-Indol-2-one,3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-|Indirubin [MI]|3-(1,3-dihydro-3-oxo-2h-indol-2-ylidene)-1,3-dihydro-2h-indol-2-on|Indirubin 3E-form [MI]|Indigopurpurin|Indirubin|(Z)-[2,3 inverted exclamation mark -Biindolinylidene]-2 inverted exclamation mark ,3-dione|EM-A05-INDIRUBIN|2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-

Storage

Store at 2-8°C

Shipped In

Wet ice

Übersicht

Indirubin, also known as isoindigotin, is an inhibitor of cyclin-dependent kinases (CDK1/cyclin B (IC50 = 10μM), CDK2/cyclin A (IC50 = 2.2μM), CDK2/cyclin E (IC50 = 7.5μM), CDK4/cyclin D1 (IC50 = 12μM), CDK5/p35 (IC50 = 5.5μM)) and of GSK-3β (IC50 = 600nM). Studies investigating functional isoindigos show that they have the ability to disrupt cell growth and proliferation. The compound is a potent aryl hydrocarbon receptor ligand and is found in human urine and fetal bovine serum. Synthesized isoindigo-based oligothiophenes are used to study heterojunction solar cells. Shown to inhibit allergic contact dermatitis by regulating T helper mediated immune system in a DNCB-induced model.
An inhibitor of GSK-3β and cyclin-dependent kinases.

Spezifikationen

Synonyme

(3Z)-3-(3-oxoindolin-2-ylidene)indolin-2-one | 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-, (3E)- | (3E)-3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one | (E)-[2,3'-biindolinylidene]-2',3-dione | BI164578 | (3E)-3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one | Couroupitine B | Indirubin,(S) | Iso Show more

Spezifikationen & Reinheit

analytical standard, ≥95%

Biochemische und physiologische Mechanismen

Potent cyclin-dependent kinase (CDK) and GSK-3β inhibitor (IC 50 values are 5.5 μM at CDK5, 9 μM at CDK1 and 600 nM at GSK-3β). Antimitotic and antitumoral properties induces cell cycle arrest, inhibits cell proliferation AMPK, LCK and SGK. Inhibits CDK5-

Storage

Store at 2-8°C

Verschickt in

Wet ice

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Note

Analytischer Standard

Hinweis

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.

Reinheit

≥95%

Namen und Kennungen

Pubchem Sid

508817076

Kanonisches Lächeln

C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O

IUPAC Name

2-(2-hydroxy-1H-indol-3-yl)indol-3-one

InChIKey

JNLNPCNGMHKCKO-UHFFFAOYSA-N

INCHI

1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,18,20H

Isomere SMILES

C1=CC=C2C(=C1)C(=C(N2)O)C3=NC4=CC=CC=C4C3=O

Molekulargewicht

262.26

Reaxy-Rn

30107462

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30107462&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Klasse Indoles and derivatives
      • Subclass Hydroxyindoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Indoles and derivatives
• Subclass: Hydroxyindoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxyindoles
• Alternative Parents: Indoles Aryl ketones Substituted pyrroles Benzenoids Heteroaromatic compounds Ketimines Propargyl-type 1,3-dipolar organic compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydroxyindole - Indole - Aryl ketone - Benzenoid - Substituted pyrrole - Pyrrole - Heteroaromatic compound - Ketimine - Ketone - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Imine - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
• External Descriptors: Not available

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

Chemische und physikalische Eigenschaften

• Löslichkeit: Soluble in DMSO(warmed) (>2 mg/ml).
• Empfindlichkeit: Heat sensitive.
• Schmelzpunkt (°C): 350°C(lit.)
• Molekulargewicht: 262.260 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 262.074 Da
• Monoisotopic Mass: 262.074 Da
• Topological Polar Surface Area: 65.500 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 448.000
• 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