N-(3-(cyclopentyloxy)-4-methoxyphenyl)-8-hydroxyquinoline-2-carboxamide

ID: ALA4475112

PubChem CID: 155537465

Max Phase: Preclinical

Molecular Formula: C22H22N2O4

Molecular Weight: 378.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=O)c2ccc3cccc(O)c3n2)cc1OC1CCCC1

Standard InChI:  InChI=1S/C22H22N2O4/c1-27-19-12-10-15(13-20(19)28-16-6-2-3-7-16)23-22(26)17-11-9-14-5-4-8-18(25)21(14)24-17/h4-5,8-13,16,25H,2-3,6-7H2,1H3,(H,23,26)

Standard InChI Key:  KIEVMXVQRNMTHK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    0.6702  -15.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782  -15.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3764  -14.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780  -16.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0851  -14.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0858  -15.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943  -15.7214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5026  -15.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979  -14.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888  -14.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119  -15.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2151  -16.5336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9180  -15.3051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6273  -15.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6258  -16.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3343  -16.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0414  -16.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0356  -15.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3265  -15.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7402  -15.2856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7342  -14.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512  -16.9258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4568  -16.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3866  -13.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1283  -13.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3111  -13.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0645  -13.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  7  2  0
  6  4  2  0
  4  1  1  0
  3  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  9 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 19 21  1  0
 21 22  1  0
 18 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475112

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.43

Molecular Weight (Monoisotopic): 378.1580

AlogP: 4.52

#Rotatable Bonds: 5

Polar Surface Area: 80.68

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.18

CX Basic pKa: 0.23

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: -0.66

References

1. Hu J, Pan T, An B, Li Z, Li X, Huang L..  (2019)  Synthesis and evaluation of clioquinol-rolipram/roflumilast hybrids as multitarget-directed ligands for the treatment of Alzheimer's disease.,  163  [PMID:30553143] [10.1016/j.ejmech.2018.12.013]

Source

Source(1):

• Scientific Literature