N-(2-(difluoromethoxy)benzyl)-N-(3-methyl-1-(methylamino)-1-oxobutan-2-yl)-2-(pyrrolidine-1-carbonyl)-1H-imidazole-4-carboxamide

ID: ALA4741059

PubChem CID: 162645898

Max Phase: Preclinical

Molecular Formula: C23H29F2N5O4

Molecular Weight: 477.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)C(C(C)C)N(Cc1ccccc1OC(F)F)C(=O)c1c[nH]c(C(=O)N2CCCC2)n1

Standard InChI:  InChI=1S/C23H29F2N5O4/c1-14(2)18(20(31)26-3)30(13-15-8-4-5-9-17(15)34-23(24)25)21(32)16-12-27-19(28-16)22(33)29-10-6-7-11-29/h4-5,8-9,12,14,18,23H,6-7,10-11,13H2,1-3H3,(H,26,31)(H,27,28)

Standard InChI Key:  HXHYLKWFNMMLJU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    3.2648   -5.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9220   -5.8074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5882   -5.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3415   -4.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5252   -4.5484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4853   -5.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8831   -5.0144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3079   -6.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8262   -3.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6410   -3.9888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1251   -3.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8013   -2.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885   -2.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4994   -3.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2885   -1.9280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9659   -4.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7778   -4.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0986   -5.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9096   -5.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3974   -5.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0683   -4.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2582   -4.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6101   -6.2365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9333   -6.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4365   -7.6298    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7449   -7.0825    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9638   -1.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716   -4.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2282   -3.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757   -4.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0778   -5.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9369   -3.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4240   -2.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4662   -3.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  1  6  1  0
  6  7  1  0
  6  8  2  0
  4  9  1  0
  9 10  1  0
  9 14  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 15 27  1  0
  7 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31  7  1  0
 11 32  1  0
 32 33  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741059

   ---

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: 477.51

Molecular Weight (Monoisotopic): 477.2188

AlogP: 2.66

#Rotatable Bonds: 9

Polar Surface Area: 107.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 0.04

CX LogP: 2.46

CX LogD: 2.46

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.58

Np Likeness Score: -1.27

References

1. Veerman JJN,Bruseker YB,Damen E,Heijne EH,van Bruggen W,Hekking KFW,Winkel R,Hupp CD,Keefe AD,Liu J,Thomson HA,Zhang Y,Cuozzo JW,McRiner AJ,Mulvihill MJ,van Rijnsbergen P,Zech B,Renzetti LM,Babiss L,Müller G.  (2021)  Discovery of 2,4-1H-Imidazole Carboxamides as Potent and Selective TAK1 Inhibitors.,  12  (4.0): [PMID:33859795] [10.1021/acsmedchemlett.0c00547]

Source

Source(1):

• Scientific Literature