(E)-Ethyl 3-(2-amino-1-cyanovinyl)-6,7-dichloro-1-methyl-1H-indole-2-carboxylate

ID: ALA4090007

PubChem CID: 98073446

Max Phase: Preclinical

Molecular Formula: C15H13Cl2N3O2

Molecular Weight: 338.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c(/C(C#N)=C/N)c2ccc(Cl)c(Cl)c2n1C

Standard InChI:  InChI=1S/C15H13Cl2N3O2/c1-3-22-15(21)14-11(8(6-18)7-19)9-4-5-10(16)12(17)13(9)20(14)2/h4-6H,3,18H2,1-2H3/b8-6+

Standard InChI Key:  CXJCGSPAPOTTSF-SOFGYWHQSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    7.4448   -6.3698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2540   -6.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6137   -5.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3048   -5.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0237   -5.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0504   -4.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3590   -3.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6393   -4.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6161   -5.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8766   -6.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965   -5.5268    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9437   -3.8996    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4309   -5.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8466   -6.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8323   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2298   -4.3156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6371   -7.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2036   -7.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4538   -7.2342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6638   -6.4363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8369   -7.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6536   -7.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  5  1  0
  4  1  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  9 11  1  0
  8 12  1  0
  3 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  3  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
 14 20  1  0
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4090007

   ethyl 3-[(1E)-2-amino-1-cyanoeth-1-en-1-yl]-6,7-dichloro-1-methyl-1H-indole-2-carboxylate

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: 338.19

Molecular Weight (Monoisotopic): 337.0385

AlogP: 3.48

#Rotatable Bonds: 3

Polar Surface Area: 81.04

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.03

CX LogP: 3.01

CX LogD: 3.01

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -0.75

References

1. Murár M, Dobiaš J, Šramel P, Addová G, Hanquet G, Boháč A..  (2017)  Novel CLK1 inhibitors based on N-aryloxazol-2-amine skeleton - A possible way to dual VEGFR2 TK/CLK ligands.,  126  [PMID:27940419] [10.1016/j.ejmech.2016.11.003]

2. Schröder M,Bullock AN,Fedorov O,Bracher F,Chaikuad A,Knapp S.  (2020)  DFG-1 Residue Controls Inhibitor Binding Mode and Affinity, Providing a Basis for Rational Design of Kinase Inhibitor Selectivity.,  63  (18): [PMID:32787076] [10.1021/acs.jmedchem.0c00898]

Source

Source(1):

• Scientific Literature