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

ID: ALA4129161

Chembl Id: CHEMBL4129161

PubChem CID: 145962862

Max Phase: Preclinical

Molecular Formula: C26H17Cl2F2N5O2

Molecular Weight: 540.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H17Cl2F2N5O2/c27-18-6-7-19(20(28)12-18)23(13-35-10-9-31-14-35)32-24(36)15-1-3-16(4-2-15)25-33-34-26(37-25)17-5-8-21(29)22(30)11-17/h1-12,14,23H,13H2,(H,32,36)/t23-/m0/s1

Standard InChI Key:  AZQFCMJDNRLROF-QHCPKHFHSA-N

Alternative Forms

1. Parent:

   

   ALA4129161

   ---

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: 540.36

Molecular Weight (Monoisotopic): 539.0727

AlogP: 6.36

#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: 5.26

CX LogD: 5.20

Aromatic Rings: 5

Heavy Atoms: 37

QED Weighted: 0.26

Np Likeness Score: -1.71

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, Rachakonda G, Blobaum AL, Fisher P, de Oliveira GM, da Silva CF, Soeiro MNC, Nes WD, Lindsley CW, Villalta F, Guengerich FP, Lepesheva GI..  (2018)  Sterol 14α-Demethylase Structure-Based Optimization of Drug Candidates for Human Infections with the Protozoan Trypanosomatidae.,  61  (23): [PMID:30451500] [10.1021/acs.jmedchem.8b01671]

3. 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]

4. 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