Benzyl ((S)-1-Oxo-3-phenyl-1-(((S,E)-4-(pyrimidin-2-yl)but-3-en-2-yl)amino)propan-2-yl)carbamate

ID: ALA4553211

PubChem CID: 155555416

Max Phase: Preclinical

Molecular Formula: C25H26N4O3

Molecular Weight: 430.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](/C=C/c1ncccn1)NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C25H26N4O3/c1-19(13-14-23-26-15-8-16-27-23)28-24(30)22(17-20-9-4-2-5-10-20)29-25(31)32-18-21-11-6-3-7-12-21/h2-16,19,22H,17-18H2,1H3,(H,28,30)(H,29,31)/b14-13+/t19-,22-/m0/s1

Standard InChI Key:  SFCIWRSHBYODBA-SMNLDCJUSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   11.2096   -7.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8418   -8.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5480   -7.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2572   -8.2567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5449   -7.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9634   -7.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6726   -8.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3788   -7.8401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6757   -9.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0880   -8.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7942   -7.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0911   -9.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5034   -8.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9603   -7.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6665   -6.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3733   -7.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0790   -6.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0763   -5.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3621   -5.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6594   -5.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9184   -8.2381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6240   -7.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6213   -7.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9071   -6.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2044   -7.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1340   -7.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -8.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7254   -7.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -8.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0225   -9.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326   -9.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4333   -9.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  6
 11 13  2  0
 13  1  1  0
  6 14  1  1
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25  1  1  0
  2 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553211

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 430.51

Molecular Weight (Monoisotopic): 430.2005

AlogP: 3.53

#Rotatable Bonds: 9

Polar Surface Area: 93.21

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.24

CX Basic pKa: 1.89

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -0.22

References

1. Chenna BC, Li L, Mellott DM, Zhai X, Siqueira-Neto JL, Calvet Alvarez C, Bernatchez JA, Desormeaux E, Alvarez Hernandez E, Gomez J, McKerrow JH, Cruz-Reyes J, Meek TD..  (2020)  Peptidomimetic Vinyl Heterocyclic Inhibitors of Cruzain Effect Antitrypanosomal Activity.,  63  (6): [PMID:32125159] [10.1021/acs.jmedchem.9b02078]

Source

Source(1):

• Scientific Literature