methyl 3-(4-(aminomethyl)-1-(6,7,8,9-tetrahydro-5H-pyrimido[4,5-b]indol-4-yl)piperidine-4-carboxamido)benzoate

ID: ALA3797937

PubChem CID: 127047689

Max Phase: Preclinical

Molecular Formula: C25H30N6O3

Molecular Weight: 462.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cccc(NC(=O)C2(CN)CCN(c3ncnc4[nH]c5c(c34)CCCC5)CC2)c1

Standard InChI:  InChI=1S/C25H30N6O3/c1-34-23(32)16-5-4-6-17(13-16)29-24(33)25(14-26)9-11-31(12-10-25)22-20-18-7-2-3-8-19(18)30-21(20)27-15-28-22/h4-6,13,15H,2-3,7-12,14,26H2,1H3,(H,29,33)(H,27,28,30)

Standard InChI Key:  IQXFPGQRIPGJOH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   -3.7006    0.8244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5059    3.0395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107    3.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8223    5.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291    6.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2243    5.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2127    3.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8347    6.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347    6.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2441    7.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0712    6.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3652    6.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714    6.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633    6.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9489    8.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428    9.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3510    8.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2716    6.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8449    7.9382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2852    4.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5631    6.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6092    6.2447    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
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 20 30  1  0
 14 31  1  0
 30 32  2  0
 30 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3797937

   ---

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: 462.55

Molecular Weight (Monoisotopic): 462.2379

AlogP: 2.81

#Rotatable Bonds: 5

Polar Surface Area: 126.23

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.38

CX Basic pKa: 9.16

CX LogP: 3.11

CX LogD: 1.35

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.50

Np Likeness Score: -0.96

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