(R)-N-(1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl)-4-(5-(3-fluoro-4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-yl)benzamide

ID: ALA4127493

Chembl Id: CHEMBL4127493

PubChem CID: 145962573

Max Phase: Preclinical

Molecular Formula: C27H17Cl2F4N5O2

Molecular Weight: 590.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cn1ccnc1)c1ccc(Cl)cc1Cl)c1ccc(-c2nnc(-c3ccc(C(F)(F)F)c(F)c3)o2)cc1

Standard InChI:  InChI=1S/C27H17Cl2F4N5O2/c28-18-6-7-19(21(29)12-18)23(13-38-10-9-34-14-38)35-24(39)15-1-3-16(4-2-15)25-36-37-26(40-25)17-5-8-20(22(30)11-17)27(31,32)33/h1-12,14,23H,13H2,(H,35,39)/t23-/m0/s1

Standard InChI Key:  JHTFJHHUVZQQDT-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA4127493

   ---

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: 590.36

Molecular Weight (Monoisotopic): 589.0695

AlogP: 7.24

#Rotatable Bonds: 7

Polar Surface Area: 85.84

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 6.78

CX LogP: 6.00

CX LogD: 5.93

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.20

Np Likeness Score: -1.48

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]

2. Hargrove TY, Wawrzak Z, Rachakonda G, Nes WD, Villalta F, Guengerich FP, Lepesheva GI..  (2021)  Relaxed Substrate Requirements of Sterol 14α-Demethylase from Naegleria fowleri Are Accompanied by Resistance to Inhibition.,  64  (23.0): [PMID:34842434] [10.1021/acs.jmedchem.1c01710]

Source

Source(1):

• Scientific Literature