(2R)-2-{[9-(propan-2-yl)-6-({[4-(pyridin-2-yl)phenyl]methyl}amino)-9H-purin-2-yl]amino}butan-1-ol

• ChemBase ID: 6075
• Molecular Formular: C24H29N7O
• Molecular Mass: 431.53336
• Monoisotopic Mass: 431.24335858
• SMILES: c1(N[C@@H](CO)CC)nc(c2c(n(cn2)C(C)C)n1)NCc1ccc(cc1)c1ncccc1
• Canonical SMILES: CC[C@@H](Nc1nc(NCc2ccc(cc2)c2ccccn2)c2c(n1)n(cn2)C(C)C)CO
• InChI: InChI=1S/C24H29N7O/c1-4-19(14-32)28-24-29-22(21-23(30-24)31(15-27-21)16(2)3)26-13-17-8-10-18(11-9-17)20-7-5-6-12-25-20/h5-12,15-16,19,32H,4,13-14H2,1-3H3,(H2,26,28,29,30)/t19-/m1/s1
• InChIKey: HOCBJBNQIQQQGT-LJQANCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[9-(propan-2-yl)-6-({[4-(pyridin-2-yl)phenyl]methyl}amino)-9H-purin-2-yl]amino}butan-1-ol
• IUPAC Traditional name: (2R)-2-{[9-isopropyl-6-({[4-(pyridin-2-yl)phenyl]methyl}amino)purin-2-yl]amino}butan-1-ol
• Synonyms: (2R)-2-({9-(1-methylethyl)-6-[(4-pyridin-2-ylbenzyl)amino]-9H-purin-2-yl}amino)butan-1-ol; (2R)-2-[[9-(1-Methylethyl)-6-[[[4-(2-pyridinyl)phenyl]methyl]amino]-9H-purin-2-yl]amino]-butanol-1; (R)-2-(1-Hydroxybut-2-ylamino)-6-[4-(2-pyridyl)phenylmethylamino]-9-iso-propylpurine; C&R8; CR8

Database IDs

• CAS Number: 294646-77-8
• MDL Number: MFCD18785641
• PubChem SID: 99444934; 160969500
• PubChem CID: 10224714

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.336885
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 3.648268
• LogD (pH = 7.4): 3.7074037
• Log P: 3.7081864
• Molar Refractivity: 128.7516 cm^3
• Polarizability: 49.398693 Å^3
• Polar Surface Area: 100.78 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.24
• LOG S: -4.39
• Solubility (Water): 1.77e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C24H29N7O

DETAILS

DrugBank - DB08463

Drug information: experimental

Sigma Aldrich - C3249

Biochem/physiol Actions
CR8 is a potent and selective inhibitor of cyclin dependent kinase (CDK1, 2, 5, 7, and 9). CR8 is a more potent pyridyl analogue of roscovitine (Cat. No. R7772). In comparison to roscovirtine, the compound gains in potency toward CK1, which is involved in amyloid-β formation. The R-CR8 enantiomer is slightly more potent than S. CR8 is around 30 times more potent at cellular assay then roscovitine.