ID: ALA552465

Max Phase: Preclinical

Molecular Formula: C16H14ClN3O3

Molecular Weight: 331.76

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(/C=C/c1ccc(NC(=O)Nc2ccc(Cl)cc2)cc1)NO

Standard InChI:  InChI=1S/C16H14ClN3O3/c17-12-4-8-14(9-5-12)19-16(22)18-13-6-1-11(2-7-13)3-10-15(21)20-23/h1-10,23H,(H,20,21)(H2,18,19,22)/b10-3+

Standard InChI Key:  BPQUKDOJAFTDQI-XCVCLJGOSA-N

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

Properties

Molecular Weight: 331.76

Molecular Weight (Monoisotopic): 331.0724

AlogP: 3.50

#Rotatable Bonds: 4

Polar Surface Area: 90.46

Molecular Species: NEUTRAL

HBA: 3

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.55

CX Basic pKa:

CX LogP: 3.08

CX LogD: 3.07

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: -0.80

References

1. Chen Y, Li H, Tang W, Zhu C, Jiang Y, Zou J, Yu Q, You Q..  (2009)  3D-QSAR studies of HDACs inhibitors using pharmacophore-based alignment.,  44  (7): [PMID:19136179] [10.1016/j.ejmech.2008.12.008]

2. Noureen N, Rashid H, Kalsoom S.  (2012)  An efficient anticancer histone deacetylase inhibitor and its analogues for human HDAC8,  21  (5): [10.1007/s00044-011-9571-y]

3.  (2014)  Inhibitors of histone deacetylase and prodrugs thereof, 

4. Tavares MT,de Almeida LC,Kronenberger T,Monteiro Ferreira G,Fujii de Divitiis T,Franco Zannini Junqueira Toledo M,Mariko Aymoto Hassimotto N,Agostinho Machado-Neto J,Veras Costa-Lotufo L,Parise-Filho R.  (2021)  Structure-activity relationship and mechanistic studies for a series of cinnamyl hydroxamate histone deacetylase inhibitors.,  35  [PMID:33668008] [10.1016/j.bmc.2021.116085]

Source

Source(2):

• Scientific Literature
• BindingDB Database