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

ID: ALA4127305

Chembl Id: CHEMBL4127305

PubChem CID: 145962361

Max Phase: Preclinical

Molecular Formula: C31H21Cl2FN6O2

Molecular Weight: 599.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cn1ccnc1)c1ccc(Cl)cc1Cl)c1ccc(-c2nnc(-c3cc(-c4ccccn4)ccc3F)o2)cc1

Standard InChI:  InChI=1S/C31H21Cl2FN6O2/c32-22-9-10-23(25(33)16-22)28(17-40-14-13-35-18-40)37-29(41)19-4-6-20(7-5-19)30-38-39-31(42-30)24-15-21(8-11-26(24)34)27-3-1-2-12-36-27/h1-16,18,28H,17H2,(H,37,41)/t28-/m0/s1

Standard InChI Key:  ZCHVYCOGYQOQMI-NDEPHWFRSA-N

Alternative Forms

1. Parent:

   

   ALA4127305

   ---

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: 599.45

Molecular Weight (Monoisotopic): 598.1087

AlogP: 7.28

#Rotatable Bonds: 8

Polar Surface Area: 98.73

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 6.78

CX LogP: 5.94

CX LogD: 5.87

Aromatic Rings: 6

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: -1.62

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. Friggeri L, Hargrove TY, Wawrzak Z, Guengerich FP, Lepesheva GI..  (2019)  Validation of Human Sterol 14α-Demethylase (CYP51) Druggability: Structure-Guided Design, Synthesis, and Evaluation of Stoichiometric, Functionally Irreversible Inhibitors.,  62  (22): [PMID:31663733] [10.1021/acs.jmedchem.9b01485]

Source

Source(1):

• Scientific Literature