(3S,5R)-3-(2-Butyl-5-chloro-3H-imidazol-4-yl)-2-phenyl-isoxazolidine-5-carboxylic acid butyl ester

ID: ALA183641

Chembl Id: CHEMBL183641

PubChem CID: 44391473

Max Phase: Preclinical

Molecular Formula: C21H28ClN3O3

Molecular Weight: 405.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC(=O)[C@H]1C[C@@H](c2[nH]c(CCCC)nc2Cl)N(c2ccccc2)O1

Standard InChI:  InChI=1S/C21H28ClN3O3/c1-3-5-12-18-23-19(20(22)24-18)16-14-17(21(26)27-13-6-4-2)28-25(16)15-10-8-7-9-11-15/h7-11,16-17H,3-6,12-14H2,1-2H3,(H,23,24)/t16-,17+/m0/s1

Standard InChI Key:  MPOYUINHKJFZKL-DLBZAZTESA-N

Alternative Forms

1. Parent:

   

   ALA183641

   butyl (3S,5R)-3-(2-butyl-4-chloro-1H-imidazol-5-yl)-2-phenyl-1,2-oxazolidine-5-carboxylate

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: 405.93

Molecular Weight (Monoisotopic): 405.1819

AlogP: 5.00

#Rotatable Bonds: 9

Polar Surface Area: 67.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.75

CX Basic pKa: 4.39

CX LogP: 5.25

CX LogD: 5.25

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -0.71

References

1. Sadashiva MP, Mallesha H, Karunakara Murthy K, Rangappa KS..  (2005)  Enhancement in antimicrobial activity of 2-(phenyl)-3-(2-butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazolidine.,  15  (7): [PMID:15780612] [10.1016/j.bmcl.2005.02.034]

2. Sadashiva MP, Mallesha H, Karunakara Murthy K, Rangappa KS..  (2005)  Enhancement in antimicrobial activity of 2-(phenyl)-3-(2-butyl-4-chloro-1H-imidazolyl)-5-butylate isoxazolidine.,  15  (7): [PMID:15780612] [10.1016/j.bmcl.2005.02.034]

Source

Source(1):

• Scientific Literature