4-(6-{4-[2-(piperidin-1-yl)ethoxy]phenyl}pyrazolo[1,5-a]pyrimidin-3-yl)pyridine

• ChemBase ID: 6205
• Molecular Formular: C24H25N5O
• Molecular Mass: 399.4882
• Monoisotopic Mass: 399.20591045
• SMILES: C1CCCCN1CCOc1ccc(cc1)c1cn2c(nc1)c(cn2)c1ccncc1
• Canonical SMILES: C1CCN(CC1)CCOc1ccc(cc1)c1cnc2n(c1)ncc2c1ccncc1
• InChI: InChI=1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2
• InChIKey: XHBVYDAKJHETMP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(6-{4-[2-(piperidin-1-yl)ethoxy]phenyl}pyrazolo[1,5-a]pyrimidin-3-yl)pyridine
• IUPAC Traditional name: 4-(6-{4-[2-(piperidin-1-yl)ethoxy]phenyl}pyrazolo[1,5-a]pyrimidin-3-yl)pyridine
• Synonyms: 6-[4-(2-piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine; AMPK Inhibitor; Compound C; Dorsomorphin; 6-[4-(2-Piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine

Database IDs

• CAS Number: 866405-64-3
• MDL Number: MFCD08705402
• PubChem SID: 99445068; 24898658; 160969630
• PubChem CID: 11524144

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.3366812
• LogD (pH = 7.4): 2.0200543
• Log P: 3.4410903
• Molar Refractivity: 128.5134 cm^3
• Polarizability: 47.837887 Å^3
• Polar Surface Area: 55.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.84
• LOG S: -4.43
• Solubility (Water): 1.48e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >2 mg/mL (warmed)
• Apperance: white to beige powder

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C24H25N5O

DETAILS

DrugBank - DB08597

Drug information: experimental

Sigma Aldrich - P5499

Biochem/physiol Actions
Dorsomorphin is a selective inhibitor of Bone morphogenetic protein (BMP) signaling. It has been found to inhibit BMP signals required for embryogenesis and promoted significant neural differentiation from human pluripotent stem cell (hPSC) lines. Dorsomorphin also acts as a potent, selective, reversible, and ATP-competitive inhibitor of AMPK (AMP-activated protein kinase); Ki = 109 nM in the presence of 5 μM ATP and the absence of AMP).