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

ID: ALA511765

Chembl Id: CHEMBL511765

PubChem CID: 25211574

Max Phase: Preclinical

Molecular Formula: C25H27FN8O3

Molecular Weight: 506.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GSK2213727A | GSK2213727A|2-((2-((5-(2-(Dimethylamino)acetamido)-2-methoxy-4-methylphenyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-6-fluorobenzamide|2-{[2-({5-[2-(dimethylamino)acetamido]-2-methoxy-4-methylphenyl}amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-6-fluorobenzamide|CHEMBL511765|SCHEMBL2206654|SCHEMBL12430223|BDBM27793|IKWHWJFNGWUVIJ-UHFFFAOYSA-N|HMS3304G01|HMS3305G05|NSC756155|NSC-756155|pyrrolo[2,3-d]pyrimidine deriv., 11|NCGC00242241-01|AB01092324-01|2-[(2-{[5-[(N,N-dimethylglyShow More⌵

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

Standard InChI:  InChI=1S/C25H27FN8O3/c1-13-10-19(37-4)18(11-17(13)29-20(35)12-34(2)3)31-25-32-23-14(8-9-28-23)24(33-25)30-16-7-5-6-15(26)21(16)22(27)36/h5-11H,12H2,1-4H3,(H2,27,36)(H,29,35)(H3,28,30,31,32,33)

Standard InChI Key:  IKWHWJFNGWUVIJ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA511765

   GSK-2213727A

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: 506.54

Molecular Weight (Monoisotopic): 506.2190

AlogP: 3.50

#Rotatable Bonds: 9

Polar Surface Area: 150.29

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.57

CX Basic pKa: 7.21

CX LogP: 4.45

CX LogD: 4.23

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.23

Np Likeness Score: -1.61

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