Indirubin-3′-oxime - Moligand™, ≥98%(HPLC) , Inhibitor of glycogen synthase kinase 3 beta, CAS No.160807-49-8, Inhibitor of glycogen synthase kinase 3 beta

CAS: 160807-49-8 Cat. No.: I132661 Molecular Weight: 277.28

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

BSPBio_001108 | UNII-X6CSG51MBQ | BDBM54681 | BCBcMAP01_000150 | HBDSHCUSXQATPO-BGBJRWHRSA-N | Indirubin 3'-monoxime | Indirubin-3monoxime | INDIRUBIN-3'-MONOXIME | Indirubin-3-monoxime | AC-30025 | Indirubin-3??-oxime | EU-0100619 | FQCPPVRJPILDIK-UHFFFA

Storage

Room temperature

Shipped In

Normal

Overview

Indirubin-3'-monoxime is a potent inhibitor of GSK-3β (IC50=22 nM)1. Indirubin-3'-monoxime also inhibits CDK1 (p34cdc2; IC50=180 nM) and CDK5 (IC50=100 nM)1. Indirubin-3'-monoxime reversibly arrests asynchronous HBL-100 cells at G22. This compound induces apoptosis in the mammary carcinoma cell line MCF-7 (10 μM). Indirubin-3'-monoxime is an inhibitor of Cdk2, cyclin A, cyclin B, cyclin E and p35.
A potent inhibitor of GSK-3β, Cdk1, and Cdk5

Specifications

Synonyms

BSPBio_001108 | UNII-X6CSG51MBQ | BDBM54681 | BCBcMAP01_000150 | HBDSHCUSXQATPO-BGBJRWHRSA-N | Indirubin 3'-monoxime | Indirubin-3monoxime | INDIRUBIN-3'-MONOXIME | Indirubin-3-monoxime | AC-30025 | Indirubin-3??-oxime | EU-0100619 | FQCPPVRJPILDIK-UHFFFA

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

Indirubin-3′-oxime is a cyclin-dependent kinase inhibitor which functions by competing with ATP for binding to the catalytic subunit; exhibits antiproliferative activity leading to G2/M arrest in many cell lines and G1/S arrest in Jurkat cells.Potent GSK3

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of glycogen synthase kinase 3 beta

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%(HPLC)

Names and Identifiers

• Pubchem Sid: 504750702
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750702
• Canonical Smiles: C1=CC=C2C(=C1)C(=C(N2)O)C3=C(C4=CC=CC=C4N3)N=O
• IUPAC Name: 3-(3-nitroso-1H-indol-2-yl)-1H-indol-2-ol
• InChIKey: FQCPPVRJPILDIK-UHFFFAOYSA-N
• INCHI: 1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17-18,20H
• Isomeric SMILES: C1=CC=C2C(=C1)C(=C(N2)O)C3=C(C4=CC=CC=C4N3)N=O
• WGK Germany: 3
• Molecular Weight: 277.28
• Reaxy-Rn: 33446338
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=33446338&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Hydroxyindoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydroxyindoles
• Alternative Parents: Indoles Substituted pyrroles Benzenoids Heteroaromatic compounds C-nitroso compounds Azacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives Organic anions
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydroxyindole - Indole - Substituted pyrrole - Benzenoid - Heteroaromatic compound - Pyrrole - Azacycle - C-nitroso compound - Organic nitroso compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic oxygen compound - Organic anion - Aromatic heteropolycyclic compound
• Description: 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

Associated Targets(Human)

CYP1A2 Tchem Cytochrome P450 1A2 (1 Activities)

Discover Target: CYP1A2

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CDK5R1 Tchem Cyclin-dependent kinase 5 activator 1 (1 Activities)

Discover Target: CDK5R1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GSK3B Tclin Glycogen synthase kinase-3 beta (4 Activities)

Discover Target: GSK3B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in DMSO (6 mg/ml), ethanol (4 mg/ml), DMF (~10 mg/ml), 1:5 DMSO:PBS (pH 7.2) (0.15 mg/ml), and methanol. Insoluble in water.
• Molecular Weight: 277.280 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 277.085 Da
• Monoisotopic Mass: 277.085 Da
• Topological Polar Surface Area: 81.200 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 405.000
• 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

References

1. Liu Shou Gang, Luo Guang Pu, Qu Yong Bin, Chen Yong Feng.  (2020)  Indirubin inhibits Wnt/β-catenin signal pathway via promoter demethylation of WIF-1.  BMC Complementary Medicine and Therapies,  20  (1): (1-10).  [PMID:32795328] [10.1186/s12906-020-03045-9]