4-nitrobenzyl(S)-1-((3aS,6aS)-3-bromo-3aH-pyrrolo[3,4-d]isoxazol-5(4H,6H,6aH)-yl)-1-oxo-4-phenylbutan-2-ylcarbamate

ID: ALA3629346

Chembl Id: CHEMBL3629346

PubChem CID: 122194228

Max Phase: Preclinical

Molecular Formula: C23H23BrN4O6

Molecular Weight: 531.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H](CCc1ccccc1)C(=O)N1C[C@@H]2C(Br)=NO[C@@H]2C1)OCc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C23H23BrN4O6/c24-21-18-12-27(13-20(18)34-26-21)22(29)19(11-8-15-4-2-1-3-5-15)25-23(30)33-14-16-6-9-17(10-7-16)28(31)32/h1-7,9-10,18-20H,8,11-14H2,(H,25,30)/t18-,19-,20+/m0/s1

Standard InChI Key:  HSJSCKVJOULSOX-SLFFLAALSA-N

Alternative Forms

1. Parent:

   

   ALA3629346

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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: 531.36

Molecular Weight (Monoisotopic): 530.0801

AlogP: 3.39

#Rotatable Bonds: 8

Polar Surface Area: 123.37

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.84

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.72

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: -0.69

References

1. Ettari R, Pinto A, Previti S, Tamborini L, Angelo IC, La Pietra V, Marinelli L, Novellino E, Schirmeister T, Zappalà M, Grasso S, De Micheli C, Conti P..  (2015)  Development of novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation.,  23  (21): [PMID:26432608] [10.1016/j.bmc.2015.09.029]

Source

Source(1):

• Scientific Literature