4-Chloro-N-((S)-1-oxo-1-(((S,E)-6-oxo-1-phenylhept-4-en-3-yl)-amino)-3-phenylpropan-2-yl)benzamide

ID: ALA4584291

PubChem CID: 155566273

Max Phase: Preclinical

Molecular Formula: C29H29ClN2O3

Molecular Weight: 489.02

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)/C=C/[C@H](CCc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C29H29ClN2O3/c1-21(33)12-18-26(19-13-22-8-4-2-5-9-22)31-29(35)27(20-23-10-6-3-7-11-23)32-28(34)24-14-16-25(30)17-15-24/h2-12,14-18,26-27H,13,19-20H2,1H3,(H,31,35)(H,32,34)/b18-12+/t26-,27+/m1/s1

Standard InChI Key:  VEOFVKMRRKERDB-MOKQZDJKSA-N

Molfile:  

 
     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   24.1464   -6.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8593   -6.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8593   -5.2016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5724   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4292   -6.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7160   -6.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0029   -6.0267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2897   -6.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5724   -6.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8593   -6.4415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1462   -6.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1462   -5.2015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4330   -6.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4327   -7.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7179   -7.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0045   -7.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0022   -6.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7155   -6.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2914   -7.6745    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.5724   -5.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2897   -4.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2901   -3.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0007   -3.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7141   -3.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7163   -4.7878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0073   -5.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2897   -7.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7160   -7.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4292   -7.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4292   -8.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1463   -8.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1453   -9.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4277  -10.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7185   -9.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7158   -8.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  1  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 13 18  1  0
 16 19  1  0
  9 20  1  1
 20 21  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
 21 26  1  0
  8 27  2  0
  6 28  1  6
 28 29  1  0
 29 30  1  0
 31 30  2  0
 32 31  1  0
 33 32  2  0
 34 33  1  0
 35 34  2  0
 30 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4584291

   ---

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: 489.02

Molecular Weight (Monoisotopic): 488.1867

AlogP: 4.94

#Rotatable Bonds: 11

Polar Surface Area: 75.27

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 5.78

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.38

Np Likeness Score: -0.06

References

1. Ettari R, Previti S, Maiorana S, Amendola G, Wagner A, Cosconati S, Schirmeister T, Hellmich UA, Zappalà M..  (2019)  Optimization Strategy of Novel Peptide-Based Michael Acceptors for the Treatment of Human African Trypanosomiasis.,  62  (23): [PMID:31714776] [10.1021/acs.jmedchem.9b00908]

Source

Source(1):

• Scientific Literature