(S)-2-(3-tert-Butoxycarbonylamino-2,2-dimethyl-nonanoylamino)-3-phenyl-propionic acid ethyl ester

ID: ALA109236

PubChem CID: 10766969

Max Phase: Preclinical

Molecular Formula: C27H44N2O5

Molecular Weight: 476.66

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H44N2O5/c1-8-10-11-15-18-22(29-25(32)34-26(3,4)5)27(6,7)24(31)28-21(23(30)33-9-2)19-20-16-13-12-14-17-20/h12-14,16-17,21-22H,8-11,15,18-19H2,1-7H3,(H,28,31)(H,29,32)/t21-,22?/m0/s1

Standard InChI Key:  KEVSTWADIXQVCS-HMTLIYDFSA-N

Molfile:  

     RDKit          2D

 34 34  0  0  1  0  0  0  0  0999 V2000
    6.4750   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -5.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -5.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9000   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -5.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -4.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -4.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9000   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125   -6.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1917   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3250   -5.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375   -5.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3250   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6042   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7542   -5.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3125   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375   -3.3417    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  4  1  0
  7  2  1  0
  8  6  1  0
  9  3  1  0
 10  1  2  0
 11  3  2  0
  6 12  1  1
 13  8  2  0
 14  9  1  0
 15  8  1  0
 16  2  1  0
 17  2  1  0
 18 12  1  0
 19  7  1  0
 20 14  1  0
 21 14  1  0
 22 14  1  0
 23 15  1  0
 24 18  2  0
 25 18  1  0
 26 19  1  0
 27 28  1  0
 28 29  1  0
 29 26  1  0
 30 23  1  0
 31 27  1  0
 32 25  2  0
 33 24  1  0
 34 32  1  0
 33 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA109236

   (S)-2-(3-tert-Butoxycarbonylamino-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: 476.66

Molecular Weight (Monoisotopic): 476.3250

AlogP: 5.17

#Rotatable Bonds: 13

Polar Surface Area: 93.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.69

CX Basic pKa: ┄

CX LogP: 6.02

CX LogD: 6.02

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.30

Np Likeness Score: -0.20

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