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

ID: ALA3589668

PubChem CID: 122181020

Max Phase: Preclinical

Molecular Formula: C16H8Cl2N2O2

Molecular Weight: 331.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1nc2cc(Cl)ccc2c2[nH]c3c(Cl)cccc3c12

Standard InChI:  InChI=1S/C16H8Cl2N2O2/c17-7-4-5-8-11(6-7)19-15(16(21)22)12-9-2-1-3-10(18)13(9)20-14(8)12/h1-6,20H,(H,21,22)

Standard InChI Key:  XRQCWSSAUMCSQV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  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
    5.7161   -1.6783    0.0000 Cl  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
  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
  8 21  1  0
 16 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3589668

   ---

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: 331.16

Molecular Weight (Monoisotopic): 329.9963

AlogP: 4.87

#Rotatable Bonds: 1

Polar Surface Area: 65.98

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.63

CX Basic pKa: 3.85

CX LogP: 4.50

CX LogD: 1.12

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.52

Np Likeness Score: -0.60

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