N-{[1-(2,4-dihydroxybenzoyl)-6-(3-methylpyridin-2-yl)-1,2,3,4-tetrahydroquinolin-2-yl]methyl}methanesulfonamide

ID: ALA3719338

PubChem CID: 117967444

Max Phase: Preclinical

Molecular Formula: C24H25N3O5S

Molecular Weight: 467.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccnc1-c1ccc2c(c1)CCC(CNS(C)(=O)=O)N2C(=O)c1ccc(O)cc1O

Standard InChI:  InChI=1S/C24H25N3O5S/c1-15-4-3-11-25-23(15)17-6-10-21-16(12-17)5-7-18(14-26-33(2,31)32)27(21)24(30)20-9-8-19(28)13-22(20)29/h3-4,6,8-13,18,26,28-29H,5,7,14H2,1-2H3

Standard InChI Key:  RRVGEDSKKYXEEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.5325   -0.8904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942   -1.4919    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963   -2.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037   -5.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072   -5.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -5.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -3.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -2.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -3.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685   -5.8503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2450   -5.8341    0.0000 O   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
    0.2613   -3.5999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -0.7441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5343   -2.0902    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    3.0030    0.0000 N   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
   -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
   -5.2206   -0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  2  0
 32 27  1  0
 15 27  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3719338

   N-[[1-(2,4-dihydroxybenzoyl)-6-(3-methylpyridin-2-yl)-3,4-dihydro-2H-quinolin-2-yl]methyl]methanesulfonamide

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: 467.55

Molecular Weight (Monoisotopic): 467.1515

AlogP: 2.98

#Rotatable Bonds: 5

Polar Surface Area: 119.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.83

CX Basic pKa: 4.92

CX LogP: 2.71

CX LogD: 2.57

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: -0.81

References

1.  (2015)  Tetrahydroisoquinoline compounds and their 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. 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):

• Patent Bioactivity Data