3-(5-(2,3-Diphenylpropanamido)pyridin-2-yl)-N-hydroxyacrylamide

ID: ALA3426804

PubChem CID: 118737400

Max Phase: Preclinical

Molecular Formula: C23H21N3O3

Molecular Weight: 387.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(NC(=O)C(Cc2ccccc2)c2ccccc2)cn1)NO

Standard InChI:  InChI=1S/C23H21N3O3/c27-22(26-29)14-13-19-11-12-20(16-24-19)25-23(28)21(18-9-5-2-6-10-18)15-17-7-3-1-4-8-17/h1-14,16,21,29H,15H2,(H,25,28)(H,26,27)/b14-13+

Standard InChI Key:  UQSIPNLHOWORHA-BUHFOSPRSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.8933   -3.7570    0.0000 C   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
    2.5973   -1.5031    0.0000 C   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
    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 N   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
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -0.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0994    0.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3984    1.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3985    2.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0995    3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    2.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2029    2.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5023    3.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5029    5.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2041    5.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048    5.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9042    3.7446    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
    4.9292   -5.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1 28  1  0
 28 29  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 11 15  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 13 16  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 12 22  1  0
  8 15  1  0
  3  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3426804

   ---

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: 387.44

Molecular Weight (Monoisotopic): 387.1583

AlogP: 3.57

#Rotatable Bonds: 7

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: 9.51

CX Basic pKa: 3.63

CX LogP: 3.54

CX LogD: 3.53

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -0.79

References

1. Di Pompo G, Salerno M, Rotili D, Valente S, Zwergel C, Avnet S, Lattanzi G, Baldini N, Mai A..  (2015)  Novel histone deacetylase inhibitors induce growth arrest, apoptosis, and differentiation in sarcoma cancer stem cells.,  58  (9): [PMID:25905694] [10.1021/acs.jmedchem.5b00126]

2. Lopes JR, Chiba DE, Dos Santos JL..  (2021)  HIV latency reversal agents: A potential path for functional cure?,  213  [PMID:33540228] [10.1016/j.ejmech.2021.113213]

3. Barone S, Cassese E, Alfano AI, Brindisi M, Summa V..  (2022)  Chasing a Breath of Fresh Air in Cystic Fibrosis (CF): Therapeutic Potential of Selective HDAC6 Inhibitors to Tackle Multiple Pathways in CF Pathophysiology.,  65  (4.0): [PMID:35148101] [10.1021/acs.jmedchem.1c02067]

Source

Source(1):

• Scientific Literature