N-({4-[2-(diethylamino)ethoxy]phenyl}methyl)-2,4-dihydroxy-N-[4-(3-methylquinolin-2-yl)phenyl]benzamide

ID: ALA3730436

PubChem CID: 117968082

Max Phase: Preclinical

Molecular Formula: C36H37N3O4

Molecular Weight: 575.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCOc1ccc(CN(C(=O)c2ccc(O)cc2O)c2ccc(-c3nc4ccccc4cc3C)cc2)cc1

Standard InChI:  InChI=1S/C36H37N3O4/c1-4-38(5-2)20-21-43-31-17-10-26(11-18-31)24-39(36(42)32-19-16-30(40)23-34(32)41)29-14-12-27(13-15-29)35-25(3)22-28-8-6-7-9-33(28)37-35/h6-19,22-23,40-41H,4-5,20-21,24H2,1-3H3

Standard InChI Key:  GHNVNCXYLHYQDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 43 47  0  0  0  0  0  0  0  0999 V2000
   -3.8595    7.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1511    8.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4574    7.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4721    6.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804    5.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741    5.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144    8.0867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4907    8.1323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7776    5.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8120    5.8902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7902    3.7811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0957    3.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1082    1.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4965    3.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    1.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125    0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8985    3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4119    0.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4214   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1271   -1.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8233   -0.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8139    0.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 N   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
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1335   -2.9609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8374   -3.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8438   -5.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5477   -5.9752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5541   -7.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5178   -8.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2430   -5.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2074   -5.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486   -1.3517    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
 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
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 13  1  0
 17 25  1  0
 25 26  2  0
 26 38  1  0
 37 27  1  0
 27 28  2  0
 28 25  1  0
 22 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 37  2  0
 28 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3730436

   N-[[4-[2-(diethylamino)ethoxy]phenyl]methyl]-2,4-dihydroxy-N-[4-(3-methylquinolin-2-yl)phenyl]benzamide

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: 575.71

Molecular Weight (Monoisotopic): 575.2784

AlogP: 7.19

#Rotatable Bonds: 11

Polar Surface Area: 86.13

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.81

CX Basic pKa: 9.70

CX LogP: 5.99

CX LogD: 5.67

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.17

Np Likeness Score: -1.01

References

1.  (2015)  Resorcinol n-aryl amide compounds, for use as pyruvate dehydrogenase kinase inhibitors, 

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

3. Meng, Tao T and 10 more authors.  2014-12-11  Discovery and optimization of 4,5-diarylisoxazoles as potent dual inhibitors of pyruvate dehydrogenase kinase and heat shock protein 90.  [PMID:25383915]

4. 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]

5. Narayan, Satya S and 7 more authors.  2019-01-01  ASR352, A potent anticancer agent: Synthesis, preliminary SAR, and biological activities against colorectal cancer bulk, 5-fluorouracil/oxaliplatin resistant and stem cells.  [PMID:30384048]

Source

Source(1):

• Patent Bioactivity Data