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

• ChemBase ID: 153822
• Molecular Formular: C16H10BrN3O2
• Molecular Mass: 356.1735
• Monoisotopic Mass: 354.99563858
• SMILES: c1ccc2c(c1)/C(=N\O)/C(=C\1/c3ccc(cc3NC1=O)Br)/N2
• Canonical SMILES: O/N=C\1/C(=C/2\C(=O)Nc3c2ccc(c3)Br)/Nc2c1cccc2
• InChI: InChI=1S/C16H10BrN3O2/c17-8-5-6-9-12(7-8)19-16(21)13(9)15-14(20-22)10-3-1-2-4-11(10)18-15/h1-7,18,22H,(H,19,21)
• InChIKey: DDLZLOKCJHBUHD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-bromo-3-[3-(hydroxyimino)-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 6-bromo-3-[3-(hydroxyimino)-1H-indol-2-ylidene]-1H-indol-2-one
• Synonyms: (2’Z,3’E)-6-Bromoindirubin-3′-oxime; 6-BIO; 6BIO; BIO

Database IDs

• CAS Number: 667463-62-9
• MDL Number: MFCD08705318
• PubChem SID: 24724412; 162247961
• PubChem CID: 11405589

CALCULATED PROPERTIES

• Acid pKa: 7.838362
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.5611088
• LogD (pH = 7.4): 2.4288893
• Log P: 2.5630994
• Molar Refractivity: 90.4399 cm^3
• Polarizability: 32.187233 Å^3
• Polar Surface Area: 73.72 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: dark red powder

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C16H10BrN3O2

DETAILS

Sigma Aldrich - B1686

Packaging
air sensitive
Legal Information
Product is sold for research and laboratory purposes in vitro and may not be used for any in vivo or therapeutic uses in humans, veterinary applications, or to make chemical derivatives.
Biochem/physiol Actions
6-bromoindirubin-3′-oxime (BIO) is a potent, reversible and ATP-competitive GSK-3α/β inhibitor and the first pharmacological agent shown to maintain self-renewal in human and mouse embryonic stem cells. Human embryonic stem cells (hESCs) are maintained in the undifferentiated state through treatment with a GSK-3 inhibitor, BIO, under a feeder-free condition.