(Z)-5-((6-Chloro-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

ID: ALA4786972

PubChem CID: 162668027

Max Phase: Preclinical

Molecular Formula: C22H27ClN4O2

Molecular Weight: 414.94

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(CC)CCNC(=O)c1c(C)[nH]c(/C=C2\C(=O)Nc3cc(Cl)ccc32)c1C

Standard InChI:  InChI=1S/C22H27ClN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)18(25-14(20)4)12-17-16-8-7-15(23)11-19(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-

Standard InChI Key:  JPQIKBXALJNAKG-ATVHPVEESA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   28.3082  -16.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3069  -17.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0218  -18.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0200  -16.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7354  -16.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7357  -17.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5261  -17.9055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0145  -17.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5257  -16.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7805  -15.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8395  -17.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5880  -15.6059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1397  -16.2173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8916  -15.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8048  -15.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9991  -14.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6628  -14.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4173  -14.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2022  -14.7642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2449  -13.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6065  -16.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8148  -14.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5997  -14.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2122  -13.9129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.9972  -14.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6097  -13.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0399  -13.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6524  -12.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5887  -18.0591    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  9 10  2  0
 10 12  1  0
  8 11  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  2  0
 14 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4786972

   ---

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: 414.94

Molecular Weight (Monoisotopic): 414.1823

AlogP: 3.85

#Rotatable Bonds: 7

Polar Surface Area: 77.23

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.09

CX Basic pKa: 9.04

CX LogP: 3.39

CX LogD: 1.74

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -1.08

References

1. Matheson CJ,Casalvieri KA,Backos DS,Minhajuddin M,Jordan CT,Reigan P.  (2020)  Substituted oxindol-3-ylidenes as AMP-activated protein kinase (AMPK) inhibitors.,  197  [PMID:32334266] [10.1016/j.ejmech.2020.112316]

Source

Source(1):

• Scientific Literature