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

ID: ALA113418

PubChem CID: 10721621

Max Phase: Preclinical

Molecular Formula: C34H47N3O4

Molecular Weight: 561.77

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C34H47N3O4/c1-5-7-8-9-10-11-12-16-19-30(37-31(38)28-22-20-27(25-35)21-23-28)34(3,4)33(40)36-29(32(39)41-6-2)24-26-17-14-13-15-18-26/h13-15,17-18,20-23,29-30H,5-12,16,19,24H2,1-4H3,(H,36,40)(H,37,38)/t29-,30?/m0/s1

Standard InChI Key:  MSZKILTZRNCRGX-UFXYQILXSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA113418

   ethyl (2S)-2-[[3-[(4-cyanobenzoyl)amino]-2,2-dimethyltridecanoyl]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: 561.77

Molecular Weight (Monoisotopic): 561.3567

AlogP: 6.50

#Rotatable Bonds: 18

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: 12.18

CX Basic pKa: ┄

CX LogP: 7.84

CX LogD: 7.84

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.16

Np Likeness Score: -0.44

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