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

ID: ALA4779166

PubChem CID: 162662723

Max Phase: Preclinical

Molecular Formula: C22H27FN4O2

Molecular Weight: 398.48

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H27FN4O2/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:  HCSLNMZYDZLMOP-ATVHPVEESA-N

Molfile:  

 
     RDKit          2D

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   19.6218  -18.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3366  -18.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3348  -16.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0502  -17.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0504  -18.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8409  -18.4001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3292  -17.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8405  -17.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0952  -16.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1542  -17.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9027  -16.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4542  -16.7120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2062  -16.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1193  -15.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3137  -15.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9774  -14.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7318  -15.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5167  -15.2589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5594  -14.1980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9210  -16.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1291  -14.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9141  -14.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5265  -14.4076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3114  -14.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9239  -14.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3542  -13.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9667  -13.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9036  -18.5536    0.0000 F   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
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  6  7  1  0
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  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:

   

   ALA4779166

   ---

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: 398.48

Molecular Weight (Monoisotopic): 398.2118

AlogP: 3.33

#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: 10.94

CX Basic pKa: 9.04

CX LogP: 2.84

CX LogD: 1.28

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -1.16

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