N-(2-(difluoromethoxy)-4-methoxybenzyl)-N-(2-(methylamino)-2-oxoethyl)-2-(pyrrolidine-1-carbonyl)-1H-imidazole-4-carboxamide

ID: ALA4778091

PubChem CID: 162643931

Max Phase: Preclinical

Molecular Formula: C21H25F2N5O5

Molecular Weight: 465.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)CN(Cc1ccc(OC)cc1OC(F)F)C(=O)c1c[nH]c(C(=O)N2CCCC2)n1

Standard InChI:  InChI=1S/C21H25F2N5O5/c1-24-17(29)12-28(11-13-5-6-14(32-2)9-16(13)33-21(22)23)19(30)15-10-25-18(26-15)20(31)27-7-3-4-8-27/h5-6,9-10,21H,3-4,7-8,11-12H2,1-2H3,(H,24,29)(H,25,26)

Standard InChI Key:  AHHCKRNAMPGQBA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   13.9502  -13.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6074  -14.4374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2736  -13.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0269  -13.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2106  -13.1784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1706  -14.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5685  -13.6445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9933  -14.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5116  -12.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3264  -12.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8105  -11.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4867  -11.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6739  -11.1214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1848  -11.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9739  -10.5580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6513  -13.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4632  -13.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7840  -14.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5950  -14.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0827  -13.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7537  -12.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9436  -12.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2955  -14.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6186  -15.6171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1219  -16.2599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.4302  -15.7126    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.6492   -9.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6570  -12.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9136  -12.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3611  -13.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7632  -13.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8947  -13.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2207  -14.4901    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
 20 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778091

   ---

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: 1.64

#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: 0.85

CX LogD: 0.85

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.58

Np Likeness Score: -1.60

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