(R)-4-(5-(3-Chloro-4-(methylsulfonyl)phenyl)-1,3,4-oxadiazol-2-yl)-N-(1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl)benzamide

ID: ALA4127446

Chembl Id: CHEMBL4127446

PubChem CID: 145960880

Max Phase: Preclinical

Molecular Formula: C27H20Cl3N5O4S

Molecular Weight: 616.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1ccc(-c2nnc(-c3ccc(C(=O)N[C@@H](Cn4ccnc4)c4ccc(Cl)cc4Cl)cc3)o2)cc1Cl

Standard InChI:  InChI=1S/C27H20Cl3N5O4S/c1-40(37,38)24-9-6-18(12-22(24)30)27-34-33-26(39-27)17-4-2-16(3-5-17)25(36)32-23(14-35-11-10-31-15-35)20-8-7-19(28)13-21(20)29/h2-13,15,23H,14H2,1H3,(H,32,36)/t23-/m0/s1

Standard InChI Key:  DYSKNETXBJKLOF-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA4127446

   ---

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: 616.91

Molecular Weight (Monoisotopic): 615.0302

AlogP: 6.14

#Rotatable Bonds: 8

Polar Surface Area: 119.98

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 6.78

CX LogP: 4.42

CX LogD: 4.36

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.22

Np Likeness Score: -1.52

References

1. Friggeri L, Hargrove TY, Wawrzak Z, Blobaum AL, Rachakonda G, Lindsley CW, Villalta F, Nes WD, Botta M, Guengerich FP, Lepesheva GI..  (2018)  Sterol 14α-Demethylase Structure-Based Design of VNI (( R)- N-(1-(2,4-Dichlorophenyl)-2-(1 H-imidazol-1-yl)ethyl)-4-(5-phenyl-1,3,4-oxadiazol-2-yl)benzamide)) Derivatives To Target Fungal Infections: Synthesis, Biological Evaluation, and Crystallographic Analysis.,  61  (13): [PMID:29894182] [10.1021/acs.jmedchem.8b00641]

Source

Source(1):

• Scientific Literature