(E)-3-[1-(3-Dimethylamino-2,2-dimethylpropyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]-N-hydroxyacrylamide

ID: ALA1830397

Chembl Id: CHEMBL1830397

PubChem CID: 16068056

Max Phase: Preclinical

Molecular Formula: C22H34N4O2

Molecular Weight: 386.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CC(C)(C)Cn1c(CC(C)(C)C)nc2cc(/C=C/C(=O)NO)ccc21

Standard InChI:  InChI=1S/C22H34N4O2/c1-21(2,3)13-19-23-17-12-16(9-11-20(27)24-28)8-10-18(17)26(19)15-22(4,5)14-25(6)7/h8-12,28H,13-15H2,1-7H3,(H,24,27)/b11-9+

Standard InChI Key:  FDURBWFXDKGGLQ-PKNBQFBNSA-N

Alternative Forms

1. Parent:

   

   ALA1830397

   (E)-3-[1-[3-(dimethylamino)-2,2-dimethylpropyl]-2-(2,2-dimethylpropyl)benzimidazol-5-yl]-N-hydroxyprop-2-enamide

2. Alternative Forms:

   

   ALA1830397

   (E)-3-[1-[3-(dimethylamino)-2,2-dimethylpropyl]-2-(2,2-dimethylpropyl)benzimidazol-5-yl]-N-hydroxyprop-2-enamide;dihydrochloride

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: 386.54

Molecular Weight (Monoisotopic): 386.2682

AlogP: 3.73

#Rotatable Bonds: 7

Polar Surface Area: 70.39

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.32

CX Basic pKa: 9.93

CX LogP: 3.01

CX LogD: 1.48

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -0.86

References

1. Wang H, Yu N, Chen D, Lee KC, Lye PL, Chang JW, Deng W, Ng MC, Lu T, Khoo ML, Poulsen A, Sangthongpitag K, Wu X, Hu C, Goh KC, Wang X, Fang L, Goh KL, Khng HH, Goh SK, Yeo P, Liu X, Bonday Z, Wood JM, Dymock BW, Kantharaj E, Sun ET..  (2011)  Discovery of (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl}-N-hydroxyacrylamide (SB939), an orally active histone deacetylase inhibitor with a superior preclinical profile.,  54  (13): [PMID:21634430] [10.1021/jm2003552]

Source

Source(1):

• Scientific Literature