6-{1,1-Dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl}-N-(8-hydroxyquinolin-5-yl)hexanamide

ID: ALA4555080

PubChem CID: 155556307

Max Phase: Preclinical

Molecular Formula: C22H21N3O5S

Molecular Weight: 439.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCCCCN1C(=O)c2ccccc2S1(=O)=O)Nc1ccc(O)c2ncccc12

Standard InChI:  InChI=1S/C22H21N3O5S/c26-18-12-11-17(15-8-6-13-23-21(15)18)24-20(27)10-2-1-5-14-25-22(28)16-7-3-4-9-19(16)31(25,29)30/h3-4,6-9,11-13,26H,1-2,5,10,14H2,(H,24,27)

Standard InChI Key:  FHUWHICQBYOHBL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.1005  -22.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2792  -22.1992    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6919  -22.9111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6211  -23.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6217  -22.6852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9524  -22.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2095  -21.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0294  -21.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4376  -20.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0312  -20.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2082  -20.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7996  -20.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1753  -22.4564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9004  -23.5099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1841  -23.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4684  -23.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7563  -23.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6067  -23.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5989  -24.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3085  -25.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0227  -24.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3126  -23.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0194  -23.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7250  -23.5129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7249  -22.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0134  -22.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3107  -22.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7346  -25.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1834  -24.7434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0448  -23.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3326  -23.9198    0.0000 C   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  2  1  0
  2  8  1  0
  7  6  1  0
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  6 13  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 23  1  0
 22 18  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 22  2  0
 21 28  1  0
 15 29  2  0
 17 30  1  0
 30 31  1  0
 31  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555080

   ---

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: 439.49

Molecular Weight (Monoisotopic): 439.1202

AlogP: 3.28

#Rotatable Bonds: 7

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: 2.85

CX LogD: 2.83

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.27

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