10-Chloro-3-ethoxy-11H-indolo[3,2-c]quinoline-6-carboxylic acid

ID: ALA3589669

PubChem CID: 122181021

Max Phase: Preclinical

Molecular Formula: C18H13ClN2O3

Molecular Weight: 340.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc2c(c1)nc(C(=O)O)c1c3cccc(Cl)c3[nH]c21

Standard InChI:  InChI=1S/C18H13ClN2O3/c1-2-24-9-6-7-10-13(8-9)20-17(18(22)23)14-11-4-3-5-12(19)15(11)21-16(10)14/h3-8,21H,2H2,1H3,(H,22,23)

Standard InChI Key:  GZABGNNMQYCDLS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    2.0934    1.7370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236    2.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340    0.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0891   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5812   -0.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0934   -2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632   -2.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5431   -1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4942    0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0690   -1.3585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8484    0.9353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728    2.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426    1.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103    0.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7636   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2938   -0.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377    3.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9260    4.3734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0399    3.6994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1001   -1.9758    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0080   -1.7520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0242   -0.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1954   -0.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  1 10  1  0
  5 10  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 11 17  1  0
 12 17  2  0
  3 12  1  0
  4 11  1  0
 18 19  2  0
 18 20  1  0
  2 18  1  0
 16 21  1  0
  8 22  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3589669

   ---

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: 340.77

Molecular Weight (Monoisotopic): 340.0615

AlogP: 4.62

#Rotatable Bonds: 3

Polar Surface Area: 75.21

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.77

CX Basic pKa: 4.17

CX LogP: 4.10

CX LogD: 0.72

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -0.64

References

1. Falke H, Chaikuad A, Becker A, Loaëc N, Lozach O, Abu Jhaisha S, Becker W, Jones PG, Preu L, Baumann K, Knapp S, Meijer L, Kunick C..  (2015)  10-iodo-11H-indolo[3,2-c]quinoline-6-carboxylic acids are selective inhibitors of DYRK1A.,  58  (7): [PMID:25730262] [10.1021/jm501994d]

Source

Source(1):

• Scientific Literature