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

ID: ALA108199

PubChem CID: 10792160

Max Phase: Preclinical

Molecular Formula: C30H38FN3O4

Molecular Weight: 523.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCC(NC(=O)c1ccc(C#N)cc1F)C(C)(C)C(=O)N[C@@H](Cc1ccccc1)C(=O)OCC

Standard InChI:  InChI=1S/C30H38FN3O4/c1-5-7-8-12-15-26(34-27(35)23-17-16-22(20-32)18-24(23)31)30(3,4)29(37)33-25(28(36)38-6-2)19-21-13-10-9-11-14-21/h9-11,13-14,16-18,25-26H,5-8,12,15,19H2,1-4H3,(H,33,37)(H,34,35)/t25-,26?/m0/s1

Standard InChI Key:  VKIDTJKSWDRVBP-PMCHYTPCSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA108199

   ethyl (2S)-2-[[3-[(4-cyano-2-fluorobenzoyl)amino]-2,2-dimethylnonanoyl]amino]-3-phenylpropanoate

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: 523.65

Molecular Weight (Monoisotopic): 523.2846

AlogP: 5.08

#Rotatable Bonds: 14

Polar Surface Area: 108.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.03

CX Basic pKa: ┄

CX LogP: 6.20

CX LogD: 6.20

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.27

Np Likeness Score: -0.76

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