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

ID: ALA320750

PubChem CID: 10552062

Max Phase: Preclinical

Molecular Formula: C27H33N3O4

Molecular Weight: 463.58

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H33N3O4/c1-6-34-25(32)22(16-19-10-8-7-9-11-19)29-26(33)27(4,5)23(18(2)3)30-24(31)21-14-12-20(17-28)13-15-21/h7-15,18,22-23H,6,16H2,1-5H3,(H,29,33)(H,30,31)/t22-,23?/m0/s1

Standard InChI Key:  XQDNXZJOQLJUEY-NQCNTLBGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA320750

   (S)-2-[3-(4-Cyano-benzoylamino)-2,2,4-trimethyl-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: 463.58

Molecular Weight (Monoisotopic): 463.2471

AlogP: 3.63

#Rotatable Bonds: 10

Polar Surface Area: 108.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.13

CX Basic pKa: ┄

CX LogP: 4.64

CX LogD: 4.64

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.52

Np Likeness Score: -0.66

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