({[((E)-(S)-1-Benzyl-4-fluoro-but-2-enylcarbamoyl)-methyl]-carbamoyl}-methyl)-carbamic acid benzyl ester

ID: ALA308013

PubChem CID: 44311441

Max Phase: Preclinical

Molecular Formula: C23H26FN3O4

Molecular Weight: 427.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CNC(=O)OCc1ccccc1)NCC(=O)N[C@H](/C=C/CF)Cc1ccccc1

Standard InChI:  InChI=1S/C23H26FN3O4/c24-13-7-12-20(14-18-8-3-1-4-9-18)27-22(29)16-25-21(28)15-26-23(30)31-17-19-10-5-2-6-11-19/h1-12,20H,13-17H2,(H,25,28)(H,26,30)(H,27,29)/b12-7+/t20-/m1/s1

Standard InChI Key:  CYCWNUHFFZNJNW-ACGJQVIASA-N

Molfile:  

     RDKit          2D

 31 32  0  0  1  0  0  0  0  0999 V2000
    3.2917   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -3.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -4.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -3.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -5.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -2.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -3.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4542   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917   -3.2542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -7.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 15  1  0
  3 14  1  0
  4  2  1  0
  5  1  1  0
  6  3  1  0
  7  1  2  0
  8  1  1  0
  9  2  2  0
 10  3  2  0
 11 12  1  0
 12  4  1  0
 13 11  2  0
 14  5  1  0
 15  6  1  0
 12 16  1  1
 17  8  1  0
 18 16  1  0
 19 21  1  0
 20 17  1  0
 21 13  1  0
 22 18  1  0
 23 18  2  0
 24 20  2  0
 25 20  1  0
 26 25  2  0
 27 24  1  0
 28 23  1  0
 29 22  2  0
 30 28  2  0
 31 26  1  0
 27 31  2  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA308013

   benzyl N-[2-[[2-[[(E,2S)-5-fluoro-1-phenylpent-3-en-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]carbamate

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: 427.48

Molecular Weight (Monoisotopic): 427.1907

AlogP: 2.28

#Rotatable Bonds: 11

Polar Surface Area: 96.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.69

CX Basic pKa: ┄

CX LogP: 2.13

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.48

Np Likeness Score: -0.47

References

1. Ohba T, Ikeda E, Wakayama J, Takei H.  (1996)  Irreversible inhibitions of serine proteases by peptidyl allylic halide derivatives,  6  (3): [10.1016/0960-894X(95)00592-H]

Source

Source(1):

• Scientific Literature