6,7-dimethyl-3-{[methyl({2-[methyl({1-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl}methyl)amino]ethyl})amino]methyl}-4H-chromen-4-one dihydrochloride

• ChemBase ID: 154069
• Molecular Formular: C32H34Cl2F3N3O2
• Molecular Mass: 620.5324696
• Monoisotopic Mass: 619.19801736
• SMILES: Cc1cc2c(cc1C)occ(c2=O)CN(C)CCN(C)Cc1cn(c2c1cccc2)c1cccc(c1)C(F)(F)F.Cl.Cl
• Canonical SMILES: CN(Cc1cn(c2c1cccc2)c1cccc(c1)C(F)(F)F)CCN(Cc1coc2c(c1=O)cc(c(c2)C)C)C.Cl.Cl
• InChI: InChI=1S/C32H32F3N3O2.2ClH/c1-21-14-28-30(15-22(21)2)40-20-24(31(28)39)18-37(4)13-12-36(3)17-23-19-38(29-11-6-5-10-27(23)29)26-9-7-8-25(16-26)32(33,34)35;;/h5-11,14-16,19-20H,12-13,17-18H2,1-4H3;2*1H
• InChIKey: GOZMBJCYMQQACI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7-dimethyl-3-{[methyl({2-[methyl({1-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl}methyl)amino]ethyl})amino]methyl}-4H-chromen-4-one dihydrochloride
• IUPAC Traditional name: 6,7-dimethyl-3-{[methyl({2-[methyl({1-[3-(trifluoromethyl)phenyl]indol-3-yl}methyl)amino]ethyl})amino]methyl}chromen-4-one dihydrochloride
• Synonyms: SPD00000304; 6,7-Dimethyl-3-[[methyl[2-[methyl[[1-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl]methyl]amino]ethyl]amino]methyl]-(4H-1-Benzopyran-4-one dihydrochloride; SPD304; 6,7-dimethyl-3-[[methyl[2-[methyl[[1-[3-(trifluoromethyl)phenyl]-1H-indol-3-yl]methyl]amino]ethyl]amino]methyl]-(4H-1-Benzopyran-4-one 二盐酸盐

Database IDs

• MDL Number: MFCD09265259
• PubChem SID: 162248208; 24724602
• PubChem CID: 16079006

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.6874096
• LogD (pH = 7.4): 5.506815
• Log P: 6.6272
• Molar Refractivity: 163.9146 cm^3
• Polarizability: 59.187473 Å^3
• Polar Surface Area: 37.71 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• 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

Pharmacology Properties

• Gene Information: human ... TNF(7124)mouse ... TNF(21926)rat ... TNF(24835)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C32H32F3N3O2 · 2HCl

DETAILS

Sigma Aldrich - S1697

Biochem/physiol Actions
SPD304 is a small molecule inhibitor of TNF-a activity with a novel mechanism of action. It interferes with protein-protein interactions on the contact surfaces of the trimeric TNF-a subunits, displacing one of the trimer units, resulting in dissociation of the trimer and loss of activity at the receptor TNFR1. SPD304 inhibits TNFR1 receptor binding to TNF-a with an IC50 of 22μM in vitro and inhibits TNF-a-mediated stimulation of IkB degradation in HeLa cells with an IC50 of 4.6 μM.