(S)-3-amino-1-(4-chlorophenyl)-4-(1H-imidazol-4-yl)butan-2-one dihydrochloride

ID: ALA519986

Chembl Id: CHEMBL519986

PubChem CID: 44307539

Max Phase: Preclinical

Molecular Formula: C13H16Cl3N3O

Molecular Weight: 263.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Cl.N[C@@H](Cc1c[nH]cn1)C(=O)Cc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C13H14ClN3O.2ClH/c14-10-3-1-9(2-4-10)5-13(18)12(15)6-11-7-16-8-17-11;;/h1-4,7-8,12H,5-6,15H2,(H,16,17);2*1H/t12-;;/m0../s1

Standard InChI Key:  PUJUKPUUKDRJKY-LTCKWSDVSA-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

Calculated Properties

Molecular Weight: 263.73

Molecular Weight (Monoisotopic): 263.0825

AlogP: 1.74

#Rotatable Bonds: 5

Polar Surface Area: 71.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.09

CX Basic pKa: 7.54

CX LogP: 1.76

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: -0.49

References

1. Abdo MR, Joseph P, Boigegrain RA, Liautard JP, Montero JL, Köhler S, Winum JY..  (2007)  Brucella suis histidinol dehydrogenase: synthesis and inhibition studies of a series of substituted benzylic ketones derived from histidine.,  15  (13): [PMID:17481905] [10.1016/j.bmc.2007.04.027]

2. Joseph P, Abdo MR, Boigegrain RA, Montero JL, Winum JY, Köhler S..  (2007)  Targeting of the Brucella suis virulence factor histidinol dehydrogenase by histidinol analogues results in inhibition of intramacrophagic multiplication of the pathogen.,  51  (10): [PMID:17698620] [10.1128/aac.00572-07]

3. Dancer JE, Ford MJ, Hamilton K, Kilkelly M, Lindell SD, O'Mahony MJ, Saville-Stones EA.  (1996)  Synthesis of potent inhibitors of histidinol dehydrogenase,  6  (17): [10.1016/0960-894X(96)00384-8]

Source

Source(1):

• Scientific Literature