3-{3-Amino-4-[(3S)-3-aminopiperidin-1-yl]quinolin-6-yl}-N-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide hydrochloride

ID: ALA4776181

PubChem CID: 135145664

Max Phase: Preclinical

Molecular Formula: C23H26ClN7O

Molecular Weight: 415.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cnc2[nH]cc(-c3ccc4ncc(N)c(N5CCC[C@H](N)C5)c4c3)c2c1.Cl

Standard InChI:  InChI=1S/C23H25N7O.ClH/c1-26-23(31)14-8-16-18(10-29-22(16)28-9-14)13-4-5-20-17(7-13)21(19(25)11-27-20)30-6-2-3-15(24)12-30;/h4-5,7-11,15H,2-3,6,12,24-25H2,1H3,(H,26,31)(H,28,29);1H/t15-;/m0./s1

Standard InChI Key:  LHSFFGVPEQSDGZ-RSAXXLAASA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   18.4239  -18.3125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.5636  -12.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5624  -13.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2705  -14.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2687  -12.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9773  -12.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9781  -13.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6866  -14.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3949  -13.7381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3901  -12.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6810  -12.5126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8571  -14.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1108  -13.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5635  -14.4312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7710  -14.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9735  -15.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7206  -15.9091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2642  -16.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0640  -16.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3131  -15.5721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6118  -16.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3607  -17.7285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9086  -18.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6880  -14.9639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9793  -15.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9791  -16.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6858  -16.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3945  -16.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3964  -15.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1016  -16.5980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4109  -16.7795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1041  -14.1439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 12 13  2  0
 13 14  1  0
 14 16  1  0
 15 12  1  0
  3 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  8 24  1  0
 28 30  1  1
 21 31  2  0
  9 32  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 415.50

Molecular Weight (Monoisotopic): 415.2121

AlogP: 2.65

#Rotatable Bonds: 3

Polar Surface Area: 125.95

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.87

CX LogP: 1.05

CX LogD: -2.04

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -0.79

References

1.  (2019)  Derivatives of quinolines as inhibitors of dyrk1a and/or dyrk1b kinases, 

Source

Source(1):

• Patent Bioactivity Data