5-{1,1-Dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl}-N-(8-hydroxyquinolin-5-yl)pentanamide

ID: ALA4527922

PubChem CID: 155544623

Max Phase: Preclinical

Molecular Formula: C21H19N3O5S

Molecular Weight: 425.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCCCN1C(=O)c2ccccc2S1(=O)=O)Nc1ccc(O)c2ncccc12

Standard InChI:  InChI=1S/C21H19N3O5S/c25-17-11-10-16(14-7-5-12-22-20(14)17)23-19(26)9-3-4-13-24-21(27)15-6-1-2-8-18(15)30(24,28)29/h1-2,5-8,10-12,25H,3-4,9,13H2,(H,23,26)

Standard InChI Key:  SZNNJYLHQXAJDQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    5.0393  -19.7323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308  -20.4463    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4519  -20.4416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2851  -22.4987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5688  -22.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8532  -22.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1411  -22.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9956  -22.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9878  -23.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6933  -24.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4075  -23.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6973  -22.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4042  -22.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1098  -22.5018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1097  -21.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3982  -21.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6955  -21.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1193  -24.1457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5682  -23.7281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295  -22.4965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302  -21.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7187  -21.2619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9652  -21.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188  -20.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8279  -20.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4208  -19.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6005  -19.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891  -20.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027  -20.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7949  -22.4028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 13  1  0
 12  8  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 12  2  0
 11 18  1  0
  5 19  2  0
  7 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
  2 25  1  0
 24 23  1  0
 23 22  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 23 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4527922

   ---

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: 425.47

Molecular Weight (Monoisotopic): 425.1045

AlogP: 2.89

#Rotatable Bonds: 6

Polar Surface Area: 116.67

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.80

CX Basic pKa: 4.57

CX LogP: 2.41

CX LogD: 2.39

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -1.35

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