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

ID: ALA4782796

PubChem CID: 162664768

Max Phase: Preclinical

Molecular Formula: C22H27BrN4O2

Molecular Weight: 459.39

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H27BrN4O2/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:  WNDUJGBGBDASMN-ATVHPVEESA-N

Molfile:  

 
     RDKit          2D

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    1.4444  -23.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433  -23.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1580  -24.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1562  -22.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8717  -23.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8719  -23.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6624  -24.1840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1507  -23.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620  -22.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167  -22.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9757  -23.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7242  -21.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2757  -22.4957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0278  -22.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9408  -21.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1352  -21.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7989  -20.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5533  -20.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3383  -21.0427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3810  -19.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7426  -22.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9508  -20.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7357  -20.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3482  -20.1914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1331  -20.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7456  -19.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1758  -19.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7883  -18.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7250  -24.3374    0.0000 Br  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:

   

   ALA4782796

   ---

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: 459.39

Molecular Weight (Monoisotopic): 458.1317

AlogP: 3.96

#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: 11.13

CX Basic pKa: 9.04

CX LogP: 3.55

CX LogD: 1.91

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -0.90

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