2-(azetidine-1-carbonyl)-N-(2-(difluoromethoxy)benzyl)-N-(2-(methylamino)-2-oxoethyl)-1H-imidazole-4-carboxamide

ID: ALA4784347

PubChem CID: 162665762

Max Phase: Preclinical

Molecular Formula: C21H25F2N5O4

Molecular Weight: 449.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)CN(Cc1ccccc1OC(F)F)C(=O)c1c[nH]c(C(=O)N2CCCCC2)n1

Standard InChI:  InChI=1S/C21H25F2N5O4/c1-24-17(29)13-28(12-14-7-3-4-8-16(14)32-21(22)23)19(30)15-11-25-18(26-15)20(31)27-9-5-2-6-10-27/h3-4,7-8,11,21H,2,5-6,9-10,12-13H2,1H3,(H,24,29)(H,25,26)

Standard InChI Key:  JNGJOWHBKZQNCQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   14.9201  -14.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5773  -15.0523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2435  -14.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9968  -13.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1805  -13.7934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1405  -14.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5384  -14.2594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9632  -15.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4815  -13.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2963  -13.2338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7804  -12.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4566  -11.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6438  -11.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1547  -12.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9438  -11.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6212  -13.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4331  -14.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7539  -14.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5649  -14.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0526  -14.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7236  -13.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9135  -13.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2654  -15.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5885  -16.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0918  -16.8748    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.4001  -16.3275    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.6191  -10.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7181  -13.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1199  -12.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3388  -13.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1593  -13.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7609  -14.5107    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
  7 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4784347

   ---

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: 449.46

Molecular Weight (Monoisotopic): 449.1875

AlogP: 2.03

#Rotatable Bonds: 8

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: 9.98

CX Basic pKa: 0.04

CX LogP: 1.45

CX LogD: 1.45

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.64

Np Likeness Score: -1.73

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