6-Benzyl-N4-((1r,3r)-3-hydroxycyclobutyl)-N2-methylpyridine-2,4-dicarboxamide

ID: ALA4876311

PubChem CID: 132167406

Max Phase: Preclinical

Molecular Formula: C19H21N3O3

Molecular Weight: 339.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(C(=O)N[C@H]2C[C@H](O)C2)cc(Cc2ccccc2)n1

Standard InChI:  InChI=1S/C19H21N3O3/c1-20-19(25)17-9-13(18(24)22-15-10-16(23)11-15)8-14(21-17)7-12-5-3-2-4-6-12/h2-6,8-9,15-16,23H,7,10-11H2,1H3,(H,20,25)(H,22,24)/t15-,16-

Standard InChI Key:  FQRNJZDJWMGBEX-WKILWMFISA-N

Molfile:  

 
     RDKit          2D

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    5.0343  -27.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290  -27.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290  -26.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0367  -25.8860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6213  -25.8860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7444  -26.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237  -27.5245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237  -28.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3290  -28.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343  -28.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166  -28.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2083  -28.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101  -27.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5026  -27.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945  -27.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983  -28.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5064  -28.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7414  -28.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7402  -29.5685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4497  -28.3437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1568  -28.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3660  -29.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1557  -29.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9453  -28.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8628  -29.7390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  4  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  2  7  1  0
  1 10  1  0
 10 18  1  0
 18 19  2  0
 18 20  1  0
 21 20  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 21  1  0
 23 25  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4876311

   ---

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: 339.40

Molecular Weight (Monoisotopic): 339.1583

AlogP: 1.29

#Rotatable Bonds: 5

Polar Surface Area: 91.32

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.60

CX Basic pKa: 0.37

CX LogP: 0.63

CX LogD: 0.63

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -0.40

References

1. Harrison LA, Atkinson SJ, Bassil A, Chung CW, Grandi P, Gray JRJ, Levernier E, Lewis A, Lugo D, Messenger C, Michon AM, Mitchell DJ, Preston A, Prinjha RK, Rioja I, Seal JT, Taylor S, Wall ID, Watson RJ, Woolven JM, Demont EH..  (2021)  Identification of a Series of N-Methylpyridine-2-carboxamides as Potent and Selective Inhibitors of the Second Bromodomain (BD2) of the Bromo and Extra Terminal Domain (BET) Proteins.,  64  (15.0): [PMID:34232650] [10.1021/acs.jmedchem.0c02155]

Source

Source(1):

• Scientific Literature