4-{2-[5-Amino-2-(3-chloro-phenyl)-6-oxo-6H-pyrimidin-1-yl]-acetylamino}-2,2-difluoro-3-oxo-5-phenyl-pentanoic acid benzylamide

ID: ALA24734

PubChem CID: 9916581

Max Phase: Preclinical

Molecular Formula: C30H26ClF2N5O4

Molecular Weight: 594.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cnc(-c2cccc(Cl)c2)n(CC(=O)NC(Cc2ccccc2)C(=O)C(F)(F)C(=O)NCc2ccccc2)c1=O

Standard InChI:  InChI=1S/C30H26ClF2N5O4/c31-22-13-7-12-21(15-22)27-35-17-23(34)28(41)38(27)18-25(39)37-24(14-19-8-3-1-4-9-19)26(40)30(32,33)29(42)36-16-20-10-5-2-6-11-20/h1-13,15,17,24H,14,16,18,34H2,(H,36,42)(H,37,39)

Standard InChI Key:  NUNGDKUJSAHDEV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA24734

   4-{2-[5-Amino-2-(3-chloro-phenyl)-6-oxo-6H-pyrimidin-1-yl]-acetylamino}-2,2-difluoro-3-oxo-5-phenyl-pentanoic acid benzylamide

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: 594.02

Molecular Weight (Monoisotopic): 593.1641

AlogP: 3.39

#Rotatable Bonds: 11

Polar Surface Area: 136.18

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.56

CX Basic pKa: 0.55

CX LogP: 4.02

CX LogD: 4.01

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.23

Np Likeness Score: -0.99

References

1. Akahoshi F, Ashimori A, Sakashita H, Yoshimura T, Eda M, Imada T, Nakajima M, Mitsutomi N, Kuwahara S, Ohtsuka T, Fukaya C, Miyazaki M, Nakamura N..  (2001)  Synthesis, structure-activity relationships, and pharmacokinetic profiles of nonpeptidic difluoromethylene ketones as novel inhibitors of human chymase.,  44  (8): [PMID:11312928] [10.1021/jm000497n]

Source

Source(1):

• Scientific Literature