2-(2-(5-(2-(dimethylamino)-N-methylacetamido)-2-methoxy-4-methylphenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-6-fluorobenzamide

ID: ALA467581

Chembl Id: CHEMBL467581

PubChem CID: 25218573

Max Phase: Preclinical

Molecular Formula: C26H29FN8O3

Molecular Weight: 520.57

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GSK2219385A | GSK2219385A|CHEMBL467581|SCHEMBL2206944|SCHEMBL12430215|BDBM27795|ZUXJDKZUOTZPMQ-UHFFFAOYSA-N|HMS3304I01|HMS3305E05|NSC756156|GSK2219385|NSC-756156|pyrrolo[2,3-d]pyrimidine deriv., 13|NCGC00242243-01|AB01092325-01|2-[(2-{[5-[(N,N-dimethylglycyl)(methyl)amino]-4-methyl-2-(methyloxy)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluorobenzamide|2-{[2-({5-[2-(dimethylamino)-N-methylacetamido]-2-methoxy-4-methylphenyl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-6-fluorobenzamShow More⌵

Canonical SMILES:  COc1cc(C)c(N(C)C(=O)CN(C)C)cc1Nc1nc(Nc2cccc(F)c2C(N)=O)c2cc[nH]c2n1

Standard InChI:  InChI=1S/C26H29FN8O3/c1-14-11-20(38-5)18(12-19(14)35(4)21(36)13-34(2)3)31-26-32-24-15(9-10-29-24)25(33-26)30-17-8-6-7-16(27)22(17)23(28)37/h6-12H,13H2,1-5H3,(H2,28,37)(H3,29,30,31,32,33)

Standard InChI Key:  ZUXJDKZUOTZPMQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA467581

   GSK-2219385A

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: 520.57

Molecular Weight (Monoisotopic): 520.2347

AlogP: 3.52

#Rotatable Bonds: 9

Polar Surface Area: 141.50

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.59

CX Basic pKa: 7.20

CX LogP: 4.31

CX LogD: 4.10

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.26

Np Likeness Score: -1.41

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, 

Source

Source(3):

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