1,5-Dimethyl-N-(2-(methylamino)-2-oxoethyl)-6-oxo-N-(2-phenylbutyl)-1,6-dihydropyridine-3-carboxamide

ID: ALA4877172

PubChem CID: 164626000

Max Phase: Preclinical

Molecular Formula: C21H27N3O3

Molecular Weight: 369.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(CN(CC(=O)NC)C(=O)c1cc(C)c(=O)n(C)c1)c1ccccc1

Standard InChI:  InChI=1S/C21H27N3O3/c1-5-16(17-9-7-6-8-10-17)13-24(14-19(25)22-3)21(27)18-11-15(2)20(26)23(4)12-18/h6-12,16H,5,13-14H2,1-4H3,(H,22,25)

Standard InChI Key:  ZGGABEHSCVFGRY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   21.4726   -9.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4714  -10.7661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1795  -11.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8891  -10.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8863   -9.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1777   -9.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7647   -9.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1752   -8.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5975  -11.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5987  -11.9903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3045  -10.7634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7634  -11.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3035   -9.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0108   -9.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0098   -8.7196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7170   -8.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7190   -9.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0128  -11.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0139  -11.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3068  -12.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7222  -12.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7193  -13.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4267  -13.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1348  -13.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1311  -12.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4230  -11.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3079  -13.2150    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  6  2  0
  6  1  1  0
  1  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 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
 20 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877172

   ---

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: 369.47

Molecular Weight (Monoisotopic): 369.2052

AlogP: 2.08

#Rotatable Bonds: 7

Polar Surface Area: 71.41

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: -1.12

References

1. Rianjongdee F, Atkinson SJ, Chung CW, Grandi P, Gray JRJ, Kaushansky LJ, Medeiros P, Messenger C, Phillipou A, Preston A, Prinjha RK, Rioja I, Satz AL, Taylor S, Wall ID, Watson RJ, Yao G, Demont EH..  (2021)  Discovery of a Highly Selective BET BD2 Inhibitor from a DNA-Encoded Library Technology Screening Hit.,  64  (15.0): [PMID:34251219] [10.1021/acs.jmedchem.1c00412]

Source

Source(1):

• Scientific Literature