3-(2-chlorophenylthio)-4-hydroxy-6-(4-hydroxyphenyl)-6-(thiophen-3-yl)-5,6-dihydropyridin-2(1H)-one

ID: ALA4521960

PubChem CID: 155542943

Max Phase: Preclinical

Molecular Formula: C21H16ClNO3S2

Molecular Weight: 429.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1NC(c2ccc(O)cc2)(c2ccsc2)CC(O)=C1Sc1ccccc1Cl

Standard InChI:  InChI=1S/C21H16ClNO3S2/c22-16-3-1-2-4-18(16)28-19-17(25)11-21(23-20(19)26,14-9-10-27-12-14)13-5-7-15(24)8-6-13/h1-10,12,24-25H,11H2,(H,23,26)

Standard InChI Key:  NPPKQFGYXIBRKS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   30.5445   -7.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2094   -7.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6893   -8.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5045   -8.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8399   -7.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3603   -7.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8367   -9.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1095   -9.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9265   -9.7563    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.1598   -8.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4854   -8.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7165   -7.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5547   -6.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5535   -7.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2616   -8.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9712   -7.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9684   -6.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2598   -6.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8468   -6.4427    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.1392   -6.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4273   -6.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7218   -6.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4254   -8.0734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1371   -7.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4284   -5.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2573   -5.6251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.8434   -8.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3964   -8.0534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
 12 11  1  0
  5 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 13 19  1  0
 19 20  1  0
 20 21  2  0
 20 24  1  0
 21 22  1  0
 22 12  1  0
 12 23  1  0
 23 24  1  0
 21 25  1  0
 18 26  1  0
 24 27  2  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521960

   ---

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: 429.95

Molecular Weight (Monoisotopic): 429.0260

AlogP: 5.43

#Rotatable Bonds: 4

Polar Surface Area: 69.56

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.95

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 2.64

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.74

References

1. Purkey HE, Robarge K, Chen J, Chen Z, Corson LB, Ding CZ, DiPasquale AG, Dragovich PS, Eigenbrot C, Evangelista M, Fauber BP, Gao Z, Ge H, Hitz A, Ho Q, Labadie SS, Lai KW, Liu W, Liu Y, Li C, Ma S, Malek S, O'Brien T, Pang J, Peterson D, Salphati L, Sideris S, Ultsch M, Wei B, Yen I, Yue Q, Zhang H, Zhou A..  (2016)  Cell Active Hydroxylactam Inhibitors of Human Lactate Dehydrogenase with Oral Bioavailability in Mice.,  7  (10): [PMID:27774125] [10.1021/acsmedchemlett.6b00190]

Source

Source(1):

• Scientific Literature