AMG 548 - ≥98%(HPLC) , MAP kinase p38 alpha inhibitor, CAS No.864249-60-5, MAP kinase p38 alpha inhibitor

CAS: 864249-60-5 Cat. No.: A288830 Molecular Weight: 461.56 EC Number: 804-485-7 PubChem CID: 11167112

GRADE & PURITY ≥98%(HPLC)

Synonyms

AMG-548 | NCGC00370979-01 | AKOS024457873 | PGR0H531I4 | (S)-2-(2-amino-3-phenylpropylamino)-3-methyl-5-(naphthalen-2-yl)-6-(pyridin-4-yl)pyrimidin-4(3H)-one | 2-[[(2S)-2-Amino-3-phenylpropyl]amino]-3-methyl-5-(2-naphthalenyl)-6-(4-pyridinyl)-4(3H)-pyrimi

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

AMG-548, an orally active and selective p38α inhibitor (Ki=0.5 nM), shows slightly selective over p38β (Ki=36 nM) and >1000 fold selective against p38γ and p38δ. AMG 548 is also extremely potent in the inhibition of whole blood LPS stimulated TNFα (IC50=3 nM)[1]. AMG-548 inhibits Wnt signaling by directly inhibiting Casein kinase 1 isoforms δ and ε.

Specifications

Synonyms

AMG-548 | NCGC00370979-01 | AKOS024457873 | PGR0H531I4 | (S)-2-(2-amino-3-phenylpropylamino)-3-methyl-5-(naphthalen-2-yl)-6-(pyridin-4-yl)pyrimidin-4(3H)-one | 2-[[(2S)-2-Amino-3-phenylpropyl]amino]-3-methyl-5-(2-naphthalenyl)-6-(4-pyridinyl)-4(3H)-pyrimi

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Potent and selective inhibitor of p38α(Kivalues are 0.5, 3.6, 2600 and 4100 nM for p38α, p38β, p38γand p38δrespectively). Displays >1000-fold selectivity against 36 other kinases; inhibits whole blood LPS-stimulated TNFα(IC50= 3 nM). Efficacious in acute

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

MAP kinase p38 alpha inhibitor

Purity

≥98%(HPLC)

Product Properties

• ALogP: 3.8

Names and Identifiers

• Canonical Smiles: CN1C(=O)C(=C(N=C1NCC(CC2=CC=CC=C2)N)C3=CC=NC=C3)C4=CC5=CC=CC=C5C=C4
• IUPAC Name: 2-[[(2S)-2-amino-3-phenylpropyl]amino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-ylpyrimidin-4-one
• InChIKey: RQVKVJIRFKVPBF-VWLOTQADSA-N
• INCHI: 1S/C29H27N5O/c1-34-28(35)26(24-12-11-21-9-5-6-10-23(21)18-24)27(22-13-15-31-16-14-22)33-29(34)32-19-25(30)17-20-7-3-2-4-8-20/h2-16,18,25H,17,19,30H2,1H3,(H,32,33)/t25-/m0/s1
• Isomeric SMILES: CN1C(=O)C(=C(N=C1NC[C@H](CC2=CC=CC=C2)N)C3=CC=NC=C3)C4=CC5=CC=CC=C5C=C4
• PubChem CID: 11167112
• Molecular Weight: 461.56

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyrimidines
• Alternative Parents: Naphthalenes Amphetamines and derivatives Pyrimidones Aralkylamines Aminopyrimidines and derivatives Pyridines and derivatives Hydropyrimidines Heteroaromatic compounds Lactams Azacyclic compounds Organooxygen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 5-phenylpyrimidine - Amphetamine or derivatives - Naphthalene - Aminopyrimidine - Pyrimidone - Aralkylamine - Benzenoid - Pyridine - Monocyclic benzene moiety - Hydropyrimidine - Heteroaromatic compound - Lactam - Azacycle - Hydrocarbon derivative - Organonitrogen compound - Organic oxygen compound - Primary aliphatic amine - Organooxygen compound - Organic oxide - Primary amine - Amine - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MAPK14 Tchem Mitogen-activated protein kinase 14 (2 Activities)

Discover Target: MAPK14

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)

Discover Target: MAPK14

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK13 Tchem MAP kinase p38 delta (2605 Activities)

Discover Target: MAPK13

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)

Discover Target: MAPK9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 49.8, Max Conc. mM: 100; Solvent:ethanol, Max Conc. mg/mL: 49.8, Max Conc. mM: 100
• Molecular Weight: 461.600 g/mol
• XLogP3: 3.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 461.222 Da
• Monoisotopic Mass: 461.222 Da
• Topological Polar Surface Area: 83.600 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 795.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1