(3-{[4-Dimethylamino-1-(5,6,7,8-tetrahydro-cyclopenta[4,5]pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carbonyl]-amino}-phenyl)-acetic acid methyl ester

ID: ALA3800261

PubChem CID: 127046988

Max Phase: Preclinical

Molecular Formula: C26H32N6O3

Molecular Weight: 476.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Cc1cccc(NC(=O)C2(N(C)C)CCN(c3ncnc4[nH]c5c(c34)CCC5)CC2)c1

Standard InChI:  InChI=1S/C26H32N6O3/c1-31(2)26(25(34)29-18-7-4-6-17(14-18)15-21(33)35-3)10-12-32(13-11-26)24-22-19-8-5-9-20(19)30-23(22)27-16-28-24/h4,6-7,14,16H,5,8-13,15H2,1-3H3,(H,29,34)(H,27,28,30)

Standard InChI Key:  AJUWMHFAMFBWMN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   -3.6810    1.1807    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1672    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485   -1.3659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2225    1.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399   -1.9215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680    2.9582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622    4.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2873    5.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8176    5.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1771    4.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2978    3.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265    6.8871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398    6.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0196    7.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6355    4.9406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061    5.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1029    4.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5720    4.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0444    5.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    6.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5785    6.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7408   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -1.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7318    0.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    1.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474    8.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021    6.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5717    3.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0412    3.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0408    2.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4171    4.7477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2158    2.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 25  1  0
 24  5  1  0
  4  8  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 11 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 24  1  0
 14 29  1  0
 14 30  1  0
 20 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3800261

   ---

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: 476.58

Molecular Weight (Monoisotopic): 476.2536

AlogP: 2.70

#Rotatable Bonds: 6

Polar Surface Area: 103.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.14

CX Basic pKa: 7.84

CX LogP: 2.94

CX LogD: 2.35

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.53

Np Likeness Score: -1.03

References

1. Alen J, Bourin A, Boland S, Geraets J, Schroeders P, Defert O.  (2016)  Tetrahydro-pyrimido-indoles as selective LIMK inhibitors: synthesis, selectivity profiling and structureactivity studies,  7  (3): [10.1039/C5MD00473J]

Source

Source(1):

• Scientific Literature