(R)-N-((R)-1-((7-chloroquinolin-4-yl)amino)-1-oxo-4-phenylbutan-2-yl)-4-methyl-2-((E)-3-(4-nitrophenyl)acrylamido)pentanamide

ID: ALA2042189

PubChem CID: 66573659

Max Phase: Preclinical

Molecular Formula: C34H34ClN5O5

Molecular Weight: 628.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](NC(=O)/C=C/c1ccc([N+](=O)[O-])cc1)C(=O)N[C@H](CCc1ccccc1)C(=O)Nc1ccnc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C34H34ClN5O5/c1-22(2)20-31(37-32(41)17-11-24-8-13-26(14-9-24)40(44)45)34(43)39-29(16-10-23-6-4-3-5-7-23)33(42)38-28-18-19-36-30-21-25(35)12-15-27(28)30/h3-9,11-15,17-19,21-22,29,31H,10,16,20H2,1-2H3,(H,37,41)(H,39,43)(H,36,38,42)/b17-11+/t29-,31-/m1/s1

Standard InChI Key:  BXNKGKQCPVSZQB-OTGPHFSISA-N

Molfile:  

     RDKit          2D

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M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2042189

   (2R)-N-[(1R)-1-[(7-chloro-4-quinolyl)carbamoyl]-3-phenyl-propyl]-4-methyl-2-[[(E)-3-(4-nitrophenyl)prop-2-enoyl]amino]pentanamide

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: 628.13

Molecular Weight (Monoisotopic): 627.2248

AlogP: 6.10

#Rotatable Bonds: 13

Polar Surface Area: 143.33

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.97

CX Basic pKa: 4.21

CX LogP: 6.55

CX LogD: 6.55

Aromatic Rings: 4

Heavy Atoms: 45

QED Weighted: 0.09

Np Likeness Score: -0.69

References

1. Pérez BC, Teixeira C, Figueiras M, Gut J, Rosenthal PJ, Gomes JR, Gomes P..  (2012)  Novel cinnamic acid/4-aminoquinoline conjugates bearing non-proteinogenic amino acids: towards the development of potential dual action antimalarials.,  54  [PMID:22683112] [10.1016/j.ejmech.2012.05.022]

Source

Source(1):

• Scientific Literature