N-(2-(difluoromethoxy)benzyl)-2-(3-methoxypyrrolidine-1-carbonyl)-N-(2-(methylamino)-2-oxoethyl)-1H-imidazole-4-carboxamide

ID: ALA4781976

PubChem CID: 162663933

Max Phase: Preclinical

Molecular Formula: C21H25F2N5O5

Molecular Weight: 465.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)CN(Cc1ccccc1OC(F)F)C(=O)c1c[nH]c(C(=O)N2CCC(OC)C2)n1

Standard InChI:  InChI=1S/C21H25F2N5O5/c1-24-17(29)12-28(10-13-5-3-4-6-16(13)33-21(22)23)19(30)15-9-25-18(26-15)20(31)27-8-7-14(11-27)32-2/h3-6,9,14,21H,7-8,10-12H2,1-2H3,(H,24,29)(H,25,26)

Standard InChI Key:  YOAISNQQOHZFFM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   31.6766  -25.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3338  -25.5314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0000  -25.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7534  -24.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9370  -24.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8971  -25.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2950  -24.7385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7197  -26.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2380  -23.6182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0528  -23.7128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5369  -23.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2132  -22.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4003  -22.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9112  -22.8733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7003  -21.6520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3778  -24.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1896  -24.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5104  -25.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3214  -25.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8092  -24.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4801  -23.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6700  -23.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0220  -25.9605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3451  -26.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8484  -27.3539    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   36.1567  -26.8065    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   34.3757  -20.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3835  -23.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6401  -23.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0876  -24.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4896  -24.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4777  -22.7871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0901  -22.2460    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
 29 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781976

   ---

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: 465.46

Molecular Weight (Monoisotopic): 465.1824

AlogP: 1.26

#Rotatable Bonds: 9

Polar Surface Area: 116.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.98

CX Basic pKa: 0.04

CX LogP: 0.50

CX LogD: 0.50

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.58

Np Likeness Score: -1.74

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