2-(2-hydroperoxy-5-hydroxy-5-methyl-2,5-dihydrofuran-2-yl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)quinoline-4-carboxamide

ID: ALA3613464

PubChem CID: 122189018

Max Phase: Preclinical

Molecular Formula: C22H17N5O5S

Molecular Weight: 463.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(O)C=CC(OO)(c2cc(C(=O)Nc3nnc(-c4ccncc4)s3)c3ccccc3n2)O1

Standard InChI:  InChI=1S/C22H17N5O5S/c1-21(29)8-9-22(31-21,32-30)17-12-15(14-4-2-3-5-16(14)24-17)18(28)25-20-27-26-19(33-20)13-6-10-23-11-7-13/h2-12,29-30H,1H3,(H,25,27,28)

Standard InChI Key:  ARVYBBKKJRWAHQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995   -2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -3.7467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2613   -3.5999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8169   -6.1073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3534   -7.5339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534   -7.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899   -6.1074    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5053  -11.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705  -11.0306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -9.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5053   -8.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    1.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957    0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4635   -0.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2113    1.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2058    2.1457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9036    0.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6812    2.1369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    3.0025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9273    3.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
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  5  6  1  0
  6  7  1  0
  7  8  2  0
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  7 11  1  0
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 24 19  1  0
  9 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
 28 30  1  0
 28 31  1  0
 25 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3613464

   ---

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: 463.48

Molecular Weight (Monoisotopic): 463.0950

AlogP: 3.34

#Rotatable Bonds: 5

Polar Surface Area: 139.58

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.72

CX Basic pKa: 2.98

CX LogP: 3.31

CX LogD: 3.15

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.23

Np Likeness Score: -0.70

References

1. Olson ME, Abate-Pella D, Perkins AL, Li M, Carpenter MA, Rathore A, Harris RS, Harki DA..  (2015)  Oxidative Reactivities of 2-Furylquinolines: Ubiquitous Scaffolds in Common High-Throughput Screening Libraries.,  58  (18): [PMID:26358009] [10.1021/acs.jmedchem.5b00930]

Source

Source(1):

• Scientific Literature