N-(2-methoxybenzyl)-N-(2-(methylamino)-2-oxoethyl)-5-(pyrrolidine-1-carbonyl)-1H-pyrrole-3-carboxamide

ID: ALA4779445

PubChem CID: 162662882

Max Phase: Preclinical

Molecular Formula: C21H26N4O4

Molecular Weight: 398.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)CN(Cc1ccccc1OC)C(=O)c1c[nH]c(C(=O)N2CCCC2)c1

Standard InChI:  InChI=1S/C21H26N4O4/c1-22-19(26)14-25(13-15-7-3-4-8-18(15)29-2)20(27)16-11-17(23-12-16)21(28)24-9-5-6-10-24/h3-4,7-8,11-12,23H,5-6,9-10,13-14H2,1-2H3,(H,22,26)

Standard InChI Key:  VBILBCHRQRVZMG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    7.6035  -14.8707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2697  -14.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0230  -13.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2067  -13.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1667  -14.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5646  -14.0778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6582  -13.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9148  -12.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3622  -13.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7643  -14.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9894  -15.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5077  -12.9575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3225  -13.0522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8066  -12.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4828  -11.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6700  -11.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1809  -12.2126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9700  -10.9914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6474  -13.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4593  -13.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7801  -14.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5911  -14.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0788  -14.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7498  -13.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9397  -13.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2916  -15.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6147  -16.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6453  -10.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  6  7  1  0
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  8  9  1  0
  9 10  1  0
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  6 12  2  0
  4 13  1  0
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 16 19  1  0
 14 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 22 27  1  0
 27 28  1  0
 19 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4779445

   ---

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: 398.46

Molecular Weight (Monoisotopic): 398.1954

AlogP: 1.65

#Rotatable Bonds: 7

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: 13.15

CX Basic pKa: ┄

CX LogP: 0.44

CX LogD: 0.44

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: -1.66

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