N-((5-Bromothiazol-2-yl)methyl)-N-(4-(dimethylcarbamoyl)phenyl)-2,4-dihydroxybenzamide

ID: ALA4461160

PubChem CID: 155528322

Max Phase: Preclinical

Molecular Formula: C20H18BrN3O4S

Molecular Weight: 476.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(C)C(=O)c1ccc(N(Cc2ncc(Br)s2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C20H18BrN3O4S/c1-23(2)19(27)12-3-5-13(6-4-12)24(11-18-22-10-17(21)29-18)20(28)15-8-7-14(25)9-16(15)26/h3-10,25-26H,11H2,1-2H3

Standard InChI Key:  LYPDEIQDNUKHGB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.7721  -26.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709  -26.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4790  -27.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886  -26.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858  -26.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772  -25.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0643  -25.7458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788  -28.1999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970  -27.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8983  -28.1979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6041  -26.9711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3124  -27.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0195  -26.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6028  -26.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3100  -25.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3090  -24.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6002  -24.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8907  -24.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952  -25.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5978  -23.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3043  -23.2971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8889  -23.3012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0132  -23.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3019  -22.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7640  -27.2971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3098  -26.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9001  -25.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1011  -26.1531    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2312  -25.2347    0.0000 Br  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
  1  7  1  0
  3  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 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
 17 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 21 24  1  0
 13 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 13  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4461160

   ---

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: 476.35

Molecular Weight (Monoisotopic): 475.0201

AlogP: 3.87

#Rotatable Bonds: 5

Polar Surface Area: 93.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: 1.10

CX LogP: 3.01

CX LogD: 2.87

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -1.24

References

1. Cho H, Shin I, Cho K, Yoon H, Yoon H, Yoo EK, Kim MJ, Park S, Lee IK, Kim ND, Sim T..  (2019)  Identification of Novel Resorcinol Amide Derivatives as Potent and Specific Pyruvate Dehydrogenase Kinase (PDHK) Inhibitors.,  62  (18): [PMID:31469962] [10.1021/acs.jmedchem.9b00565]

2. Morrell, J A JA and 5 more authors.  2003-12  AZD7545 is a selective inhibitor of pyruvate dehydrogenase kinase 2.  [PMID:14641019]

3. Moore, Jonathan D and 12 more authors.  2014-12-30  VER-246608, a novel pan-isoform ATP competitive inhibitor of pyruvate dehydrogenase kinase, disrupts Warburg metabolism and induces context-dependent cytostasis in cancer cells.  [PMID:25404640]

4. Tso, Shih-Chia and 9 more authors.  2017-02-09  Development of Dihydroxyphenyl Sulfonylisoindoline Derivatives as Liver-Targeting Pyruvate Dehydrogenase Kinase Inhibitors.  [PMID:28085286]

Source

Source(1):

• Scientific Literature