N-(2-(difluoromethoxy)benzyl)-N-(2-(methylamino)-2-oxoethyl)-5-(piperidine-1-carbonyl)-1H-pyrrole-3-carboxamide

ID: ALA4742800

PubChem CID: 162646403

Max Phase: Preclinical

Molecular Formula: C22H26F2N4O4

Molecular Weight: 448.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)CN(Cc1ccccc1OC(F)F)C(=O)c1c[nH]c(C(=O)N2CCCCC2)c1

Standard InChI:  InChI=1S/C22H26F2N4O4/c1-25-19(29)14-28(13-15-7-3-4-8-18(15)32-22(23)24)20(30)16-11-17(26-12-16)21(31)27-9-5-2-6-10-27/h3-4,7-8,11-12,22,26H,2,5-6,9-10,13-14H2,1H3,(H,25,29)

Standard InChI Key:  LGEQTKDFNLKGNQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   27.8094  -20.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4666  -21.4702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1328  -20.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8861  -20.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0698  -20.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0299  -21.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4277  -20.6773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8525  -22.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3708  -19.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1856  -19.6516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6697  -18.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3460  -18.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5331  -18.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0440  -18.8121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8331  -17.5908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5106  -20.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3224  -20.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6432  -21.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4542  -21.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9420  -20.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6129  -19.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8028  -19.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1547  -21.8993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4779  -22.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9812  -23.2927    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.2895  -22.7454    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.5085  -16.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6075  -19.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0093  -19.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2282  -19.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0487  -20.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6503  -20.9285    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:

   

   ALA4742800

   ---

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: 448.47

Molecular Weight (Monoisotopic): 448.1922

AlogP: 2.63

#Rotatable Bonds: 8

Polar Surface Area: 94.74

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.14

CX Basic pKa: ┄

CX LogP: 1.81

CX LogD: 1.81

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.65

Np Likeness Score: -1.96

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