2-(2-(4-chloro-2-methoxy-5-(1-propylpiperidin-4-yloxy)phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-6-fluorobenzamide

ID: ALA517171

Chembl Id: CHEMBL517171

Cas Number: 1123162-72-0

PubChem CID: 25218571

Max Phase: Preclinical

Molecular Formula: C28H31ClFN7O3

Molecular Weight: 568.05

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GSK1713088A | GSK1713088A|1123162-72-0|2-{[2-({4-Chloro-2-methoxy-5-[(1-propyl-4-piperidinyl)oxy]phenyl}amino)-1H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-6-fluorobenzamide|2-{[2-({4-chloro-2-methoxy-5-[(1-propylpiperidin-4-yl)oxy]phenyl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-6-fluorobenzamide|2-((2-((4-Chloro-2-methoxy-5-((1-propylpiperidin-4-yl)oxy)phenyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-6-fluorobenzamide|CHEMBL517171|BDBM27791|HMS3303N12|HMS3305G19|NSC756144|pyrrolo[2,3-d]pyrimShow More⌵

Canonical SMILES:  CCCN1CCC(Oc2cc(Nc3nc(Nc4cccc(F)c4C(N)=O)c4cc[nH]c4n3)c(OC)cc2Cl)CC1

Standard InChI:  InChI=1S/C28H31ClFN7O3/c1-3-11-37-12-8-16(9-13-37)40-22-15-21(23(39-2)14-18(22)29)34-28-35-26-17(7-10-32-26)27(36-28)33-20-6-4-5-19(30)24(20)25(31)38/h4-7,10,14-16H,3,8-9,11-13H2,1-2H3,(H2,31,38)(H3,32,33,34,35,36)

Standard InChI Key:  GGQTUXCKDZGJDL-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA517171

   GSK-1713088A

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: 568.05

Molecular Weight (Monoisotopic): 567.2161

AlogP: 5.60

#Rotatable Bonds: 10

Polar Surface Area: 130.42

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.27

CX Basic pKa: 9.07

CX LogP: 6.16

CX LogD: 4.48

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.19

Np Likeness Score: -1.34

References

1. Chamberlain SD, Redman AM, Wilson JW, Deanda F, Shotwell JB, Gerding R, Lei H, Yang B, Stevens KL, Hassell AM, Shewchuk LM, Leesnitzer MA, Smith JL, Sabbatini P, Atkins C, Groy A, Rowand JL, Kumar R, Mook RA, Moorthy G, Patnaik S..  (2009)  Optimization of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine IGF-1R tyrosine kinase inhibitors towards JNK selectivity.,  19  (2): [PMID:19071018] [10.1016/j.bmcl.2008.11.077]

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