5-{[(8-Hydroxyquinolin-5-yl)methyl]amino}-N-phenylpentanamide

ID: ALA4580239

PubChem CID: 155565303

Max Phase: Preclinical

Molecular Formula: C21H23N3O2

Molecular Weight: 349.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCCCNCc1ccc(O)c2ncccc12)Nc1ccccc1

Standard InChI:  InChI=1S/C21H23N3O2/c25-19-12-11-16(18-9-6-14-23-21(18)19)15-22-13-5-4-10-20(26)24-17-7-2-1-3-8-17/h1-3,6-9,11-12,14,22,25H,4-5,10,13,15H2,(H,24,26)

Standard InChI Key:  KPZOFDQMVMCUIC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    8.8049   -9.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5171   -9.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2281   -8.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2288   -9.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0969   -9.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3854   -9.3824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6732   -9.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9617   -9.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2496   -9.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5381   -9.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -9.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1144   -9.3790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8253  -10.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150   -8.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -8.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8283   -7.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1162   -6.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4059   -7.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084   -8.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8061   -8.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5143   -8.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5123   -7.3322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8028   -6.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0980   -7.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1035   -8.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9385   -8.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 20  1  2  0
  1  2  1  0
  2  4  2  0
  3 21  2  0
  3  4  1  0
  1  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4580239

   ---

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: 349.43

Molecular Weight (Monoisotopic): 349.1790

AlogP: 3.84

#Rotatable Bonds: 8

Polar Surface Area: 74.25

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.62

CX Basic pKa: 9.74

CX LogP: 2.36

CX LogD: 1.33

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.54

Np Likeness Score: -0.85

References

1. Chen C, Yang X, Fang H, Hou X..  (2019)  Design, synthesis and preliminary bioactivity evaluations of 8-hydroxyquinoline derivatives as matrix metalloproteinase (MMP) inhibitors.,  181  [PMID:31415980] [10.1016/j.ejmech.2019.111563]

Source

Source(1):

• Scientific Literature