2-(Adamantan-1-yl)-6,8-dichloroquinoline-4-carboxylic acid

ID: ALA3627926

PubChem CID: 633121

Max Phase: Preclinical

Molecular Formula: C20H19Cl2NO2

Molecular Weight: 376.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(C23CC4CC(CC(C4)C2)C3)nc2c(Cl)cc(Cl)cc12

Standard InChI:  InChI=1S/C20H19Cl2NO2/c21-13-4-14-15(19(24)25)6-17(23-18(14)16(22)5-13)20-7-10-1-11(8-20)3-12(2-10)9-20/h4-6,10-12H,1-3,7-9H2,(H,24,25)

Standard InChI Key:  UBEOXBXGCAWKSO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    2.5893   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5602    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8300    2.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2034   -0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    2.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614    1.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9526    2.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5715    2.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3811    0.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    0.2379    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1909    1.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0003    2.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192    3.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710    0.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4314    4.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    5.1622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869    5.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4157   -1.2816    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2671    2.4350    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 11 20  2  0
 19 14  2  0
 13 12  2  0
 12 11  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 16  2  1  0
 21 22  1  0
 21 23  2  0
 18 21  1  0
 19 24  1  0
 11 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3627926

   6,8-Dichloro-2-(1-adamantanyl)-4-quinolinecarboxylic acid

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: 376.28

Molecular Weight (Monoisotopic): 375.0793

AlogP: 5.71

#Rotatable Bonds: 2

Polar Surface Area: 50.19

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.56

CX Basic pKa: ┄

CX LogP: 5.73

CX LogD: 2.38

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -0.60

References

1. Russo CM, Adhikari AA, Wallach DR, Fernandes S, Balch AN, Kerr WG, Chisholm JD..  (2015)  Synthesis and initial evaluation of quinoline-based inhibitors of the SH2-containing inositol 5'-phosphatase (SHIP).,  25  (22): [PMID:26453006] [10.1016/j.bmcl.2015.09.034]

Source

Source(1):

• Scientific Literature