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

ID: ALA4126409

Chembl Id: CHEMBL4126409

PubChem CID: 145961897

Max Phase: Preclinical

Molecular Formula: C30H26Cl2N6O3

Molecular Weight: 589.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](Cn1ccnc1)c1ccc(Cl)cc1Cl)c1ccc(-c2nnc(-c3cccc(N4CCOCC4)c3)o2)cc1

Standard InChI:  InChI=1S/C30H26Cl2N6O3/c31-23-8-9-25(26(32)17-23)27(18-37-11-10-33-19-37)34-28(39)20-4-6-21(7-5-20)29-35-36-30(41-29)22-2-1-3-24(16-22)38-12-14-40-15-13-38/h1-11,16-17,19,27H,12-15,18H2,(H,34,39)/t27-/m0/s1

Standard InChI Key:  FNIIQAGFZKIRME-MHZLTWQESA-N

Alternative Forms

1. Parent:

   

   ALA4126409

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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: 589.48

Molecular Weight (Monoisotopic): 588.1443

AlogP: 5.91

#Rotatable Bonds: 8

Polar Surface Area: 98.31

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: 4.87

CX LogD: 4.80

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.24

Np Likeness Score: -1.63

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