(R)-3,4-dichloro-2-cyclopropyl-1-(piperidin-3-yl)-1H-pyrrolo[2,3-b]pyridine-6-carboxamide

ID: ALA4086461

PubChem CID: 137643582

Max Phase: Preclinical

Molecular Formula: C16H18Cl2N4O

Molecular Weight: 353.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cc(Cl)c2c(Cl)c(C3CC3)n([C@@H]3CCCNC3)c2n1

Standard InChI:  InChI=1S/C16H18Cl2N4O/c17-10-6-11(15(19)23)21-16-12(10)13(18)14(8-3-4-8)22(16)9-2-1-5-20-7-9/h6,8-9,20H,1-5,7H2,(H2,19,23)/t9-/m1/s1

Standard InChI Key:  DAGZBPRGFBEYDJ-SECBINFHSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    4.0763  -10.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0751  -11.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7832  -12.2275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7814  -10.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4900  -10.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4948  -11.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2748  -12.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7522  -11.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2671  -10.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671  -12.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597  -11.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3665  -13.0438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7790   -9.7730    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5319  -12.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5151   -9.9593    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9862  -13.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2403  -14.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0401  -14.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5854  -13.7766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3310  -12.9973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5701  -11.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802  -11.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2754  -10.9784    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  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
 10 11  2  0
 10 12  1  0
  4 13  1  0
 14  7  1  1
  9 15  1  0
 14 16  1  0
 14 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 22 21  1  0
 23 22  1  0
 21 23  1  0
  8 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086461

   ---

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: 353.25

Molecular Weight (Monoisotopic): 352.0858

AlogP: 3.24

#Rotatable Bonds: 3

Polar Surface Area: 72.94

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.01

CX LogP: 2.61

CX LogD: 0.09

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.89

Np Likeness Score: -0.63

References

1. Barberis C, Moorcroft N, Pribish J, Tserlin E, Gross A, Czekaj M, Barrague M, Erdman P, Majid T, Batchelor J, Levit M, Hebert A, Shen L, Moreno-Mazza S, Wang A..  (2017)  Discovery of N-substituted 7-azaindoles as Pan-PIM kinase inhibitors - Lead series identification - Part II.,  27  (20): [PMID:28927793] [10.1016/j.bmcl.2017.08.068]

Source

Source(1):

• Scientific Literature