(S)-2-[3-(4-Cyano-benzoylamino)-2,2-dimethyl-5-phenyl-pentanoylamino]-3-phenyl-propionic acid ethyl ester

ID: ALA445116

PubChem CID: 10839830

Max Phase: Preclinical

Molecular Formula: C32H35N3O4

Molecular Weight: 525.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](Cc1ccccc1)NC(=O)C(C)(C)C(CCc1ccccc1)NC(=O)c1ccc(C#N)cc1

Standard InChI:  InChI=1S/C32H35N3O4/c1-4-39-30(37)27(21-24-13-9-6-10-14-24)34-31(38)32(2,3)28(20-17-23-11-7-5-8-12-23)35-29(36)26-18-15-25(22-33)16-19-26/h5-16,18-19,27-28H,4,17,20-21H2,1-3H3,(H,34,38)(H,35,36)/t27-,28?/m0/s1

Standard InChI Key:  ZFIWICASXLPGPI-MBMZGMDYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA445116

   (S)-2-[3-(4-Cyano-benzoylamino)-2,2-dimethyl-5-phenyl-pentanoylamino]-3-phenyl-propionic acid ethyl ester

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: 525.65

Molecular Weight (Monoisotopic): 525.2628

AlogP: 4.61

#Rotatable Bonds: 12

Polar Surface Area: 108.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.17

CX Basic pKa: ┄

CX LogP: 5.86

CX LogD: 5.86

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.34

Np Likeness Score: -0.54

References

1. Iijima K, Katada J, Yasuda E, Uno I, Hayashi Y..  (1999)  N-[2,2-dimethyl-3-(N-(4-cyanobenzoyl)amino)nonanoyl]-L-phenylalanine ethyl ester as a stable ester-type inhibitor of chymotrypsin-like serine proteases: structural requirements for potent inhibition of alpha-chymotrypsin.,  42  (2): [PMID:9925737] [10.1021/jm980562h]

Source

Source(1):

• Scientific Literature