2-(Adamantan-1-yl)-6,8-dichloroquinolin-4-yl)methanol

ID: ALA3627928

PubChem CID: 122193007

Max Phase: Preclinical

Molecular Formula: C20H21Cl2NO

Molecular Weight: 362.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCc1cc(C23CC4CC(CC(C4)C2)C3)nc2c(Cl)cc(Cl)cc12

Standard InChI:  InChI=1S/C20H21Cl2NO/c21-15-5-16-14(10-24)4-18(23-19(16)17(22)6-15)20-7-11-1-12(8-20)3-13(2-11)9-20/h4-6,11-13,24H,1-3,7-10H2

Standard InChI Key:  SHEDZJNJLPJFNB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 28  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
    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
 18 21  1  0
 19 23  1  0
 11 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3627928

   ---

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: 362.30

Molecular Weight (Monoisotopic): 361.1000

AlogP: 5.50

#Rotatable Bonds: 2

Polar Surface Area: 33.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 1.90

CX LogP: 5.31

CX LogD: 5.31

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: -0.39

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