N-(2-(difluoromethoxy)-3-methoxybenzyl)-N-(2-(methylamino)-2-oxoethyl)-2-(pyrrolidine-1-carbonyl)-1H-imidazole-4-carboxamide

ID: ALA4763783

PubChem CID: 162661641

Max Phase: Preclinical

Molecular Formula: C21H25F2N5O5

Molecular Weight: 465.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)CN(Cc1cccc(OC)c1OC(F)F)C(=O)c1c[nH]c(C(=O)N2CCCC2)n1

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

Standard InChI Key:  FTXNOVULYWRUHQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.8674  -13.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5246  -14.3879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1908  -13.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441  -13.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1278  -13.1289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0878  -14.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4857  -13.5950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104  -14.9451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4288  -12.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2436  -12.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7277  -11.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4039  -11.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5911  -11.0718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1019  -11.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8911  -10.5085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685  -13.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3804  -13.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7012  -14.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5122  -14.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9999  -13.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6709  -12.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8608  -12.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2127  -14.8170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5358  -15.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0391  -16.2103    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3474  -15.6630    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5664   -9.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742  -12.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8308  -12.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2783  -13.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6803  -13.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8368  -15.0055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6486  -15.0994    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
 19 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4763783

   ---

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: -1.56

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