(S)-N-(2-(difluoromethoxy)benzyl)-N-(1-(methylamino)-1-oxopropan-2-yl)-2-(pyrrolidine-1-carbonyl)-1H-imidazole-4-carboxamide

ID: ALA4760703

PubChem CID: 162657914

Max Phase: Preclinical

Molecular Formula: C21H25F2N5O4

Molecular Weight: 449.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H25F2N5O4/c1-13(18(29)24-2)28(12-14-7-3-4-8-16(14)32-21(22)23)19(30)15-11-25-17(26-15)20(31)27-9-5-6-10-27/h3-4,7-8,11,13,21H,5-6,9-10,12H2,1-2H3,(H,24,29)(H,25,26)/t13-/m0/s1

Standard InChI Key:  UEJPPFOPQURDKT-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   22.9269   -5.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5841   -6.0509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2503   -5.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0036   -4.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1873   -4.7919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1474   -5.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5452   -5.2580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9700   -6.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4883   -4.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3031   -4.2323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7872   -3.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4635   -2.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6506   -2.7348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1615   -3.3927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9506   -2.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6281   -4.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4399   -5.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7607   -5.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5717   -5.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0595   -5.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7304   -4.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9203   -4.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2722   -6.4800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5954   -7.2306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0987   -7.8733    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.4070   -7.3260    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.6260   -1.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6338   -4.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8904   -4.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3378   -4.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7399   -5.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5990   -3.6722    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  6
M  END

Alternative Forms

1. Parent:

   

   ALA4760703

   ---

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: 2.02

#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: 1.58

CX LogD: 1.58

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.64

Np Likeness Score: -1.42

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