(Nmethyl-5-(2-oxo-2-(phenylamino)ethoxy)-2-((tetrahydro-2Hpyran-4-yl)oxy)benzamide)

ID: ALA3775323

PubChem CID: 105539871

Max Phase: Preclinical

Molecular Formula: C21H24N2O5

Molecular Weight: 384.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(OCC(=O)Nc2ccccc2)ccc1OC1CCOCC1

Standard InChI:  InChI=1S/C21H24N2O5/c1-22-21(25)18-13-17(7-8-19(18)28-16-9-11-26-12-10-16)27-14-20(24)23-15-5-3-2-4-6-15/h2-8,13,16H,9-12,14H2,1H3,(H,22,25)(H,23,24)

Standard InChI Key:  OLSMYKUQDJESEU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    1.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4884   -8.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7875   -7.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7875   -6.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4885   -5.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    4.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007    1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972    0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4920   -0.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1904   -1.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  2  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  3 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
  8 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3775323

   5-(2-anilino-2-oxoethoxy)-N-methyl-2-(oxan-4-yloxy)benzamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 384.43

Molecular Weight (Monoisotopic): 384.1685

AlogP: 2.62

#Rotatable Bonds: 7

Polar Surface Area: 85.89

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.54

CX Basic pKa: ┄

CX LogP: 1.61

CX LogD: 1.61

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: -1.15

References

1. Chaikuad A, Lang S, Brennan PE, Temperini C, Fedorov O, Hollander J, Nachane R, Abell C, Müller S, Siegal G, Knapp S..  (2016)  Structure-Based Identification of Inhibitory Fragments Targeting the p300/CBP-Associated Factor Bromodomain.,  59  (4): [PMID:26731131] [10.1021/acs.jmedchem.5b01719]

2. Humphreys PG, Bamborough P, Chung CW, Craggs PD, Gordon L, Grandi P, Hayhow TG, Hussain J, Jones KL, Lindon M, Michon AM, Renaux JF, Suckling CJ, Tough DF, Prinjha RK..  (2017)  Discovery of a Potent, Cell Penetrant, and Selective p300/CBP-Associated Factor (PCAF)/General Control Nonderepressible 5 (GCN5) Bromodomain Chemical Probe.,  60  (2): [PMID:28002667] [10.1021/acs.jmedchem.6b01566]

Source

Source(1):

• Scientific Literature