9-(propan-2-yl)-N-{[3-(trifluoromethyl)phenyl]methyl}-9H-purin-6-amine

• ChemBase ID: 155050
• Molecular Formular: C16H16F3N5
• Molecular Mass: 335.3269496
• Monoisotopic Mass: 335.1357802
• SMILES: CC(C)n1cnc2c1ncnc2NCc1cccc(c1)C(F)(F)F
• Canonical SMILES: CC(n1cnc2c1ncnc2NCc1cccc(c1)C(F)(F)F)C
• InChI: InChI=1S/C16H16F3N5/c1-10(2)24-9-23-13-14(21-8-22-15(13)24)20-7-11-4-3-5-12(6-11)16(17,18)19/h3-6,8-10H,7H2,1-2H3,(H,20,21,22)
• InChIKey: REKSFCCYDQMSIN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-(propan-2-yl)-N-{[3-(trifluoromethyl)phenyl]methyl}-9H-purin-6-amine
• IUPAC Traditional name: 9-isopropyl-N-{[3-(trifluoromethyl)phenyl]methyl}purin-6-amine
• Synonyms: 9-isopropyl-N-(3-(trifluoromethyl)benzyl)-9H-purin-6-amine; Longdaysin

Database IDs

• MDL Number: MFCD20527323
• PubChem SID: 162249188
• PubChem CID: 49830252

CALCULATED PROPERTIES

• Acid pKa: 16.229105
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.2572737
• LogD (pH = 7.4): 3.3684485
• Log P: 3.370072
• Molar Refractivity: 86.7431 cm^3
• Polarizability: 31.26041 Å^3
• Polar Surface Area: 55.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥15 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H16F3N5

DETAILS

Sigma Aldrich - SML0127

Biochem/physiol Actions
Longdaysin inhibits CK1, ERK2, and CDK7 kinases in low mM concentrations. The activity of longdaysin results in a lengthening of circadian periods in cell based and in vivo systems. Transgenic zebrafish harboring a per3-luc reporter gene displayed a 10 hour lengthening of circadian period when treated with longdaysin.