4-fluoro-2-(2-(2-methoxy-4-(1-propylpiperidin-4-yl)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)benzamide

ID: ALA476259

Chembl Id: CHEMBL476259

Cas Number: 1116234-91-3

PubChem CID: 25218601

Max Phase: Preclinical

Molecular Formula: C28H32FN7O2

Molecular Weight: 517.61

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GSK1326255A | GSK1326255A|1116234-91-3|4-Fluoro-2-[(2-{[2-methoxy-4-(1-propyl-4-piperidinyl)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide|4-fluoro-2-[(2-{[2-methoxy-4-(1-propylpiperidin-4-yl)phenyl]amino}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide|4-Fluoro-2-((2-((2-methoxy-4-(1-propylpiperidin-4-yl)phenyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)benzamide|CHEMBL476259|SCHEMBL2205722|SCHEMBL12429516|BDBM27826|HMS3303N14|HMS3305H23|NSC756141|NSC-756141|NCGC00242090-01|AB0Show More⌵

Canonical SMILES:  CCCN1CCC(c2ccc(Nc3nc(Nc4cc(F)ccc4C(N)=O)c4cc[nH]c4n3)c(OC)c2)CC1

Standard InChI:  InChI=1S/C28H32FN7O2/c1-3-12-36-13-9-17(10-14-36)18-4-7-22(24(15-18)38-2)33-28-34-26-21(8-11-31-26)27(35-28)32-23-16-19(29)5-6-20(23)25(30)37/h4-8,11,15-17H,3,9-10,12-14H2,1-2H3,(H2,30,37)(H3,31,32,33,34,35)

Standard InChI Key:  UKKOZAHWQFYYRW-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA476259

   GSK-1326255A

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: 517.61

Molecular Weight (Monoisotopic): 517.2602

AlogP: 5.28

#Rotatable Bonds: 9

Polar Surface Area: 121.19

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.92

CX Basic pKa: 9.61

CX LogP: 6.17

CX LogD: 3.95

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.24

Np Likeness Score: -1.31

References

1. Chamberlain SD, Wilson JW, Deanda F, Patnaik S, Redman AM, Yang B, Shewchuk L, Sabbatini P, Leesnitzer MA, Groy A, Atkins C, Gerding R, Hassell AM, Lei H, Mook RA, Moorthy G, Rowand JL, Stevens KL, Kumar R, Shotwell JB..  (2009)  Discovery of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidines: potent inhibitors of the IGF-1R receptor tyrosine kinase.,  19  (2): [PMID:19056263] [10.1016/j.bmcl.2008.11.046]

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, 

6. Rowlands RA, Cato MC, Waldschmidt HV, Bouley RA, Chen Q, Avramova L, Larsen SD, Tesmer JJG, White AD..  (2019)  Structure-Based Design of Selective, Covalent G Protein-Coupled Receptor Kinase 5 Inhibitors.,  10  (12): [PMID:31857838] [10.1021/acsmedchemlett.9b00365]

Source

Source(3):

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