3-[(3E)-3-(hydroxyimino)-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 1817
• Molecular Formular: C16H11N3O2
• Molecular Mass: 277.27744
• Monoisotopic Mass: 277.08512661
• SMILES: c12/C(=N\O)/C(=C\3/C(=O)Nc4c3cccc4)/Nc1cccc2
• Canonical SMILES: O/N=C\1/C(=C\2/C(=O)Nc3c2cccc3)/Nc2c1cccc2
• InChI: 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/h1-8,17,21H,(H,18,20)/b15-13-,19-14+
• InChIKey: HBDSHCUSXQATPO-BGBJRWHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3E)-3-(hydroxyimino)-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 3-[(3E)-3-(hydroxyimino)-1H-indol-2-ylidene]-1H-indol-2-one; indirubin-3'-monoxime
• Synonyms: Indirubin-3'-Monoxime; Indirubin-3′-monoxime; Indirubin-3′-oxime; Indirubin-3’-oxime; 3-[1,3-Dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one

Database IDs

• CAS Number: 160807-49-8
• MDL Number: MFCD02683594
• PubChem SID: 24278483; 46507166; 160965272
• PubChem CID: 5326739

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.309751
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.7936308
• LogD (pH = 7.4): 1.744158
• Log P: 1.7943468
• Molar Refractivity: 82.8171 cm^3
• Polarizability: 29.389532 Å^3
• Polar Surface Area: 73.72 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.18
• LOG S: -3.38
• Solubility (Water): 1.17e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL; H2O: insoluble; Methanol
• Apperance: Dark Red Solid; solid
• Melting Point: 247-249°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Light Sensitive
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (HPLC)
• Mol. Weight: mol wt 277.28

DETAILS

DrugBank - DB02052

Drug information: experimental

Sigma Aldrich - I0404

Biochem/physiol Actions
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.

Toronto Research Chemicals - I527500

A potent inhibitor of GSK-3β (IC50=22nM). Also inhibits CDK1 (IC50=180nM) and CDK (IC50=100nM). It reversibly arrests asynchronous HBL-100 cells at G2. It induces apoptosis in the mammary carcinoma cell line MCF-7 (10μM).

REFERENCES

• Leclerc, S., et al.: J. Biol. Chem., 276, 251 (2001)
• Damiens, E., et al.: Oncogene, 20, 3786 (2001)
• Marko, D., et al.: Br. J. Cancer, 84, 283 (2001)