1-[4-(4-propanoylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]-9-(quinolin-3-yl)-1H,2H-benzo[h]1,6-naphthyridin-2-one

• ChemBase ID: 178750
• Molecular Formular: C35H28F3N5O2
• Molecular Mass: 607.6243296
• Monoisotopic Mass: 607.21950982
• SMILES: c1ccc2c(c1)ncc(c2)c1ccc2c(c1)c1c(cn2)ccc(=O)n1c1cc(c(cc1)N1CCN(CC1)C(=O)CC)C(F)(F)F
• Canonical SMILES: CCC(=O)N1CCN(CC1)c1ccc(cc1C(F)(F)F)n1c(=O)ccc2c1c1cc(ccc1nc2)c1cnc2c(c1)cccc2
• InChI: InChI=1S/C35H28F3N5O2/c1-2-32(44)42-15-13-41(14-16-42)31-11-9-26(19-28(31)35(36,37)38)43-33(45)12-8-24-20-40-30-10-7-22(18-27(30)34(24)43)25-17-23-5-3-4-6-29(23)39-21-25/h3-12,17-21H,2,13-16H2,1H3
• InChIKey: AKCRNFFTGXBONI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(4-propanoylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]-9-(quinolin-3-yl)-1H,2H-benzo[h]1,6-naphthyridin-2-one
• IUPAC Traditional name: 1-[4-(4-propanoylpiperazin-1-yl)-3-(trifluoromethyl)phenyl]-9-(quinolin-3-yl)benzo[h]1,6-naphthyridin-2-one
• Synonyms: 1-[4-[4-(1-Oxopropyl)-1-piperazinyl]-3-(trifluoromethyl)phenyl]-9-(3-quinolinyl)benzo[h]-1,6-naphthyridin-2(1H)-one; Torin 1

Database IDs

• CAS Number: 1222998-36-8
• PubChem SID: 164234660
• PubChem CID: 49836027

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 5.824053
• LogD (pH = 7.4): 5.8419123
• Log P: 5.8421435
• Molar Refractivity: 166.502 cm^3
• Polarizability: 65.289925 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid
• Melting Point: >223°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: mTOR

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - T548700

Torin 1 is a potent and selective mTOR inhibitor (IC50 = 2 - 10 nM for mTORC1 and mTORC2). Displays 200-fold selectivity for mTOR over DNA-PK, ATM and hVps34.

REFERENCES

• Thoreen, et al.: J. Biol. Chem., 284, 8023 (2009)
• Liu, et al.: J. Med. Chem., 53, 7146 (2009)
• Peterson, et al.: Peterson, et al.: Cell, 146 408 (2009)