N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-5-(2-(4-aminophenyl)ethynyl)pyrimidin-4-amine

ID: ALA205966

Chembl Id: CHEMBL205966

PubChem CID: 11669455

Max Phase: Preclinical

Molecular Formula: C25H18ClFN4O

Molecular Weight: 444.90

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GW659893X | GW659893X|CHEMBL205966|SCHEMBL5922876|HMS3304H01|HMS3305E20|BDBM50182910|NSC756302|NSC-756302|NCGC00242242-01|AB01092137-01|5-((4-Aminophenyl)ethynyl)-N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)pyrimidin-4-amine|N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-5-(2-(4-aminophenyl)ethynyl)pyrimidin-4-amine

Canonical SMILES:  Nc1ccc(C#Cc2cncnc2Nc2ccc(OCc3cccc(F)c3)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C25H18ClFN4O/c26-23-13-22(10-11-24(23)32-15-18-2-1-3-20(27)12-18)31-25-19(14-29-16-30-25)7-4-17-5-8-21(28)9-6-17/h1-3,5-6,8-14,16H,15,28H2,(H,29,30,31)

Standard InChI Key:  PTARQPWAPBTGAG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA205966

   GW659893X

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 444.90

Molecular Weight (Monoisotopic): 444.1153

AlogP: 5.57

#Rotatable Bonds: 5

Polar Surface Area: 73.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.83

CX LogP: 5.69

CX LogD: 5.69

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: -1.49

References

1. Waterson AG, Stevens KL, Reno MJ, Zhang YM, Boros EE, Bouvier F, Rastagar A, Uehling DE, Dickerson SH, Reep B, McDonald OB, Wood ER, Rusnak DW, Alligood KJ, Rudolph SK..  (2006)  Alkynyl pyrimidines as dual EGFR/ErbB2 kinase inhibitors.,  16  (9): [PMID:16483772] [10.1016/j.bmcl.2006.01.111]

2. PubChem BioAssay data set, 

3. Compounds: GSK PKIS; Assays: Nanosyn kinase panel,  [10.6019/CHEMBL1961873]

4. Compounds: GSK PKIS; Assays: UNC Frye lab,  [10.6019/CHEMBL2007661]

5. Data associated with the publication PLoS ONE, 8(3), e57888, (2013) PMID: 23505445. Compounds: GSK PKIS; Assays: NIH NCATS, 

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• GSK Published Kinase Inhibitor Set