2-chloro-7-hydroxy-1-(2'-hydroxy-3'-methoxybiphenyl-4-yl)-6-phenyl-1H-pyrrolo[3,2-b]pyridin-5(4H)-one

ID: ALA2408235

PubChem CID: 54727473

Max Phase: Preclinical

Molecular Formula: C26H19ClN2O4

Molecular Weight: 458.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2ccc(-n3c(Cl)cc4[nH]c(=O)c(-c5ccccc5)c(O)c43)cc2)c1O

Standard InChI:  InChI=1S/C26H19ClN2O4/c1-33-20-9-5-8-18(24(20)30)15-10-12-17(13-11-15)29-21(27)14-19-23(29)25(31)22(26(32)28-19)16-6-3-2-4-7-16/h2-14,30H,1H3,(H2,28,31,32)

Standard InChI Key:  ZYDQKSGHSBJFMP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   28.8479  -11.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8468  -11.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5548  -12.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2645  -11.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2616  -11.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5530  -10.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5565  -13.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8471  -13.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8465  -14.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5547  -14.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2648  -14.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2619  -13.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5523  -15.5536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8917  -16.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1450  -16.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2139  -16.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9639  -16.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5091  -17.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3072  -17.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5571  -16.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0090  -15.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2581  -15.0794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8551  -17.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3523  -16.2906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9678  -10.6419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6770  -11.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9728  -12.2834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1142  -15.7830    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.9003  -16.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6949  -16.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9419  -15.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3883  -15.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5959  -15.5173    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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  3  7  1  0
 13 14  1  0
 14 15  2  0
 15 17  1  0
 16 13  1  0
 10 13  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 19 23  2  0
 20 24  1  0
  5 25  1  0
 25 26  1  0
  4 27  1  0
 14 28  1  0
 24 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2408235

   2-chloro-7-hydroxy-1-[2'-hydroxy-3'-(methyloxy)-4-biphenylyl]-6-phenyl-1,4-dihydro-5H-pyrrolo[3,2-b]pyridin-5-one

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: 458.90

Molecular Weight (Monoisotopic): 458.1033

AlogP: 5.73

#Rotatable Bonds: 4

Polar Surface Area: 87.48

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.58

CX Basic pKa: ┄

CX LogP: 4.90

CX LogD: 4.68

Aromatic Rings: 5

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -0.31

References

1. Mirguet O, Sautet S, Clément CA, Toum J, Donche F, Marques C, Rondet E, Pizzonero M, Beaufils B, Dudit Y, Huet P, Trottet L, Grondin P, Brusq JM, Boursier E, Saintillan Y, Nicodeme E..  (2013)  Discovery of Pyridones As Oral AMPK Direct Activators.,  4  (7): [PMID:24900722] [10.1021/ml400157g]

Source

Source(1):

• Scientific Literature