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

ID: ALA4788376

PubChem CID: 162669908

Max Phase: Preclinical

Molecular Formula: C25H31N5O2

Molecular Weight: 433.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(CC)CCNC(=O)c1c(C)[nH]c(/C=C2\C(=O)Nc3ccc(CCC#N)cc32)c1C

Standard InChI:  InChI=1S/C25H31N5O2/c1-5-30(6-2)13-12-27-25(32)23-16(3)22(28-17(23)4)15-20-19-14-18(8-7-11-26)9-10-21(19)29-24(20)31/h9-10,14-15,28H,5-8,12-13H2,1-4H3,(H,27,32)(H,29,31)/b20-15-

Standard InChI Key:  PIPKBPQXMOCACO-HKWRFOASSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   25.3149   -5.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3138   -5.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0286   -6.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0268   -4.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.7424   -5.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5329   -6.1548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0212   -5.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5325   -4.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7871   -4.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8462   -5.4819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5947   -3.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1463   -4.4665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8983   -4.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8114   -3.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0057   -3.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6695   -2.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4238   -2.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2088   -3.0135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2515   -1.9526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6131   -4.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8213   -2.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6062   -2.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2187   -2.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0035   -2.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6161   -1.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0463   -1.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6588   -0.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5970   -4.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5966   -3.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3109   -3.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0235   -3.0095    0.0000 N   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
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 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
  1 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4788376

   ---

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: 433.56

Molecular Weight (Monoisotopic): 433.2478

AlogP: 3.65

#Rotatable Bonds: 9

Polar Surface Area: 101.02

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.28

CX Basic pKa: 9.04

CX LogP: 2.92

CX LogD: 1.28

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: -0.86

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