(S)-3-(2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxamido)phenyl dimethylcarbamate

ID: ALA570116

Chembl Id: CHEMBL570116

Cas Number: 1116570-97-8

PubChem CID: 44543080

Max Phase: Preclinical

Molecular Formula: C22H27N7O3

Molecular Weight: 437.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c[nH]c2ncnc(N3CCN(C(=O)Nc4cccc(OC(=O)N(C)C)c4)[C@@H](C)C3)c12

Standard InChI:  InChI=1S/C22H27N7O3/c1-14-11-23-19-18(14)20(25-13-24-19)28-8-9-29(15(2)12-28)21(30)26-16-6-5-7-17(10-16)32-22(31)27(3)4/h5-7,10-11,13,15H,8-9,12H2,1-4H3,(H,26,30)(H,23,24,25)/t15-/m0/s1

Standard InChI Key:  MVPARBNSRQJBEM-HNNXBMFYSA-N

Alternative Forms

1. Parent:

   

   ALA570116

   (S)-3-(2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxamido)phenyl dimethylcarbamate

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: 437.50

Molecular Weight (Monoisotopic): 437.2175

AlogP: 3.07

#Rotatable Bonds: 3

Polar Surface Area: 106.69

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.91

CX Basic pKa: 6.20

CX LogP: 2.85

CX LogD: 2.82

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.65

Np Likeness Score: -1.54

References

1. Harrison BA, Whitlock NA, Voronkov MV, Almstead ZY, Gu KJ, Mabon R, Gardyan M, Hamman BD, Allen J, Gopinathan S, McKnight B, Crist M, Zhang Y, Liu Y, Courtney LF, Key B, Zhou J, Patel N, Yates PW, Liu Q, Wilson AG, Kimball SD, Crosson CE, Rice DS, Rawlins DB..  (2009)  Novel class of LIM-kinase 2 inhibitors for the treatment of ocular hypertension and associated glaucoma.,  52  (21): [PMID:19831390] [10.1021/jm901226j]

2. Harrison BA, Almstead ZY, Burgoon H, Gardyan M, Goodwin NC, Healy J, Liu Y, Mabon R, Marinelli B, Samala L, Zhang Y, Stouch TR, Whitlock NA, Gopinathan S, McKnight B, Wang S, Patel N, Wilson AG, Hamman BD, Rice DS, Rawlins DB..  (2015)  Discovery and Development of LX7101, a Dual LIM-Kinase and ROCK Inhibitor for the Treatment of Glaucoma.,  6  (1): [PMID:25589936] [10.1021/ml500367g]

3. Collins R, Lee H, Jones DH, Elkins JM, Gillespie JA, Thomas C, Baldwin AG, Jones K, Waters L, Paine M, Atack JR, Ward SE, Grubisha O, Foley DW..  (2022)  Comparative Analysis of Small-Molecule LIMK1/2 Inhibitors: Chemical Synthesis, Biochemistry, and Cellular Activity.,  65  (20.0): [PMID:36205722] [10.1021/acs.jmedchem.2c00751]

4. Manetti F..  (2018)  Recent advances in the rational design and development of LIM kinase inhibitors are not enough to enter clinical trials.,  155  [PMID:29908439] [10.1016/j.ejmech.2018.06.016]

Source

Source(1):

• Scientific Literature