4-hydroxy-3,3-dimethyl-2H,3H,5H-benzo[g]indole-2,5-dione

• ChemBase ID: 154429
• Molecular Formular: C14H11NO3
• Molecular Mass: 241.24204
• Monoisotopic Mass: 241.07389322
• SMILES: CC1(C2=C(C(=O)c3ccccc3C2=NC1=O)O)C
• Canonical SMILES: OC1=C2C(=NC(=O)C2(C)C)c2c(C1=O)cccc2
• InChI: InChI=1S/C14H11NO3/c1-14(2)9-10(15-13(14)18)7-5-3-4-6-8(7)11(16)12(9)17/h3-6,17H,1-2H3
• InChIKey: BAQXWJQSUXZVIP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3,3-dimethyl-2H,3H,5H-benzo[g]indole-2,5-dione
• IUPAC Traditional name: 4-hydroxy-3,3-dimethylbenzo[g]indole-2,5-dione
• Synonyms: 4-Hydroxy-3,3-dimethyl-2H-benzo[g]indole-2,5(3H)-dione; BVT.948

Database IDs

• CAS Number: 39674-97-0
• MDL Number: MFCD00616487
• PubChem SID: 162248568; 24724422
• PubChem CID: 6604934

CALCULATED PROPERTIES

• Acid pKa: 8.101262
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.3659644
• LogD (pH = 7.4): 1.288276
• Log P: 1.3670504
• Molar Refractivity: 66.6289 cm^3
• Polarizability: 24.829767 Å^3
• Polar Surface Area: 66.73 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble18 mg/mL; H2O: insoluble
• Apperance: red solid

Safety Information

• Storage Condition: desiccated; protect from light; under inert gas
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H11NO3

DETAILS

Sigma Aldrich - B6060

Biochem/physiol Actions
BVT.948 is a non-competitive inhibitor of protein tyrosine phosphatase (PTP). Enhances insulin signaling in cells and inhibits several cytochrome P450 isoforms in vitro.
Features and Benefits
BVT.948 is a non-competitive inhibitor of protein tyrosine phosphatase (PTP). Enhances insulin signaling in cells and inhibits several cytochrome P450 isoforms in vitro. Works through a different mechanism then the other PTP inhibitors. BVT.948 was able to enhance insulin signaling in cells, although it did not increase tyrosine phosphorylation globally. Furthermore, the compound was active in vivo, enhancing insulin tolerance tests in ob/ob mice, therefore apparently enhancing insulin sensitivity. BVT.948 was able to inhibit several other PTPs tested and also was efficient at inhibiting several cytochrome P450 isoforms in vitro.