(S)-2-[3-(3,5-Difluoro-benzoylamino)-2,2-dimethyl-nonanoylamino]-3-phenyl-propionic acid ethyl ester

ID: ALA108931

PubChem CID: 44338852

Max Phase: Preclinical

Molecular Formula: C29H38F2N2O4

Molecular Weight: 516.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCC(NC(=O)c1cc(F)cc(F)c1)C(C)(C)C(=O)N[C@@H](Cc1ccccc1)C(=O)OCC

Standard InChI:  InChI=1S/C29H38F2N2O4/c1-5-7-8-12-15-25(33-26(34)21-17-22(30)19-23(31)18-21)29(3,4)28(36)32-24(27(35)37-6-2)16-20-13-10-9-11-14-20/h9-11,13-14,17-19,24-25H,5-8,12,15-16H2,1-4H3,(H,32,36)(H,33,34)/t24-,25?/m0/s1

Standard InChI Key:  GSYLTNRYFPOOKL-SKCDSABHSA-N

Molfile:  

     RDKit          2D

 37 38  0  0  1  0  0  0  0  0999 V2000
    6.6667  -10.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542  -11.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167  -10.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792  -11.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292  -11.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042  -11.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417  -10.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917  -10.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042  -11.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667  -10.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917  -10.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042  -12.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167  -10.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000  -12.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792  -11.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792  -12.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917  -10.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042  -12.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5167  -10.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9625  -10.9000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917  -13.3667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417  -12.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667  -12.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -9.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417  -10.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2292  -11.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5167  -10.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8000   -8.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -9.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -7.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -8.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -8.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9500  -10.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -7.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5042   -8.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2292   -9.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2292   -8.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  1  1  0
  5  7  1  0
  6  3  1  0
  7  2  1  0
  8  4  1  0
  9  8  1  0
 10  1  2  0
 11  6  2  0
 12  6  1  0
 13  3  2  0
 14 12  2  0
 15 11  1  0
 16 14  1  0
  8 17  1  1
 18  9  2  0
 19  9  1  0
 20 15  1  0
 21 14  1  0
 22  2  1  0
 23  2  1  0
 24 17  1  0
 25  7  1  0
 26 19  1  0
 27 24  2  0
 28 24  1  0
 29 25  1  0
 30 31  1  0
 31 32  1  0
 32 29  1  0
 33 26  1  0
 34 30  1  0
 35 28  2  0
 36 27  1  0
 37 35  1  0
 37 36  2  0
 16 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA108931

   (S)-2-[3-(3,5-Difluoro-benzoylamino)-2,2-dimethyl-nonanoylamino]-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: 516.63

Molecular Weight (Monoisotopic): 516.2800

AlogP: 5.35

#Rotatable Bonds: 14

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.08

CX Basic pKa: ┄

CX LogP: 6.49

CX LogD: 6.49

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.26

Np Likeness Score: -0.46

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