(S)-2-{3-[(Furan-2-carbonyl)-amino]-2,2-dimethyl-nonanoylamino}-3-phenyl-propionic acid ethyl ester

ID: ALA323480

PubChem CID: 10790552

Max Phase: Preclinical

Molecular Formula: C27H38N2O5

Molecular Weight: 470.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCC(NC(=O)c1ccco1)C(C)(C)C(=O)N[C@@H](Cc1ccccc1)C(=O)OCC

Standard InChI:  InChI=1S/C27H38N2O5/c1-5-7-8-12-17-23(29-24(30)22-16-13-18-34-22)27(3,4)26(32)28-21(25(31)33-6-2)19-20-14-10-9-11-15-20/h9-11,13-16,18,21,23H,5-8,12,17,19H2,1-4H3,(H,28,32)(H,29,30)/t21-,23?/m0/s1

Standard InChI Key:  YUBVEMNMFILFJC-BBQAJUCSSA-N

Molfile:  

     RDKit          2D

 34 35  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
    3.0167  -12.1375    0.0000 O   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
    3.8167  -10.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500  -10.9792    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
    2.2125  -12.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000  -11.5917    0.0000 C   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
    6.3667  -12.0167    0.0000 C   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
    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
    8.8000   -8.8292    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
    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
   10.2292   -9.6500    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   -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  6  1  0
 11  1  2  0
 12  3  2  0
 13  6  2  0
  8 14  1  1
 15  9  2  0
 16 10  1  0
 17 13  1  0
 18  9  1  0
 19  2  1  0
 20  2  1  0
 21 14  1  0
 22  7  1  0
 23 18  1  0
 24 21  1  0
 25 21  2  0
 26 22  1  0
 27 28  1  0
 28 29  1  0
 29 26  1  0
 30 23  1  0
 31 27  1  0
 32 25  1  0
 33 24  2  0
 34 32  2  0
 34 33  1  0
 16 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA323480

   (S)-2-{3-[(Furan-2-carbonyl)-amino]-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: 470.61

Molecular Weight (Monoisotopic): 470.2781

AlogP: 4.67

#Rotatable Bonds: 14

Polar Surface Area: 97.64

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.24

CX Basic pKa: ┄

CX LogP: 5.26

CX LogD: 5.26

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: -0.42

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