N-(4-Acetamidobenzyl)-N-(4-(dimethylcarbamoyl)phenyl)-2,4-dihydroxybenzamide

ID: ALA4470078

PubChem CID: 155534260

Max Phase: Preclinical

Molecular Formula: C25H25N3O5

Molecular Weight: 447.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccc(CN(C(=O)c2ccc(O)cc2O)c2ccc(C(=O)N(C)C)cc2)cc1

Standard InChI:  InChI=1S/C25H25N3O5/c1-16(29)26-19-8-4-17(5-9-19)15-28(25(33)22-13-12-21(30)14-23(22)31)20-10-6-18(7-11-20)24(32)27(2)3/h4-14,30-31H,15H2,1-3H3,(H,26,29)

Standard InChI Key:  VCQLZAWRWBAQKG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.6078  -15.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6066  -16.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3147  -16.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0243  -16.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0215  -15.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3129  -15.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9000  -15.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3145  -17.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7327  -16.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7340  -17.5951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4397  -16.3682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1481  -16.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8552  -16.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5622  -16.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2688  -16.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2679  -15.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5546  -15.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8510  -15.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9745  -15.1371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6834  -15.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3899  -15.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6857  -16.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4385  -15.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1457  -15.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1447  -14.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4358  -13.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7264  -14.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7309  -15.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4335  -13.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1400  -12.6943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7246  -12.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8489  -13.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1376  -11.8771    0.0000 C   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
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 11 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4470078

   ---

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: 447.49

Molecular Weight (Monoisotopic): 447.1794

AlogP: 3.61

#Rotatable Bonds: 6

Polar Surface Area: 110.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.83

CX Basic pKa: ┄

CX LogP: 2.58

CX LogD: 2.44

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: -1.19

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