(S)-ethyl 2-(3-(4-chlorophenyl)acrylamido)-3-phenylpropanoate

ID: ALA2289692

PubChem CID: 26165761

Max Phase: Preclinical

Molecular Formula: C20H20ClNO3

Molecular Weight: 357.84

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H20ClNO3/c1-2-25-20(24)18(14-16-6-4-3-5-7-16)22-19(23)13-10-15-8-11-17(21)12-9-15/h3-13,18H,2,14H2,1H3,(H,22,23)/b13-10+/t18-/m0/s1

Standard InChI Key:  GJCJJFSIUNFDHQ-HGZMWJMZSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   34.8572   -9.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8560  -10.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5641  -10.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2737  -10.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2709   -9.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5623   -9.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9821  -10.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6891  -10.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3975  -10.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1045  -10.5260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3988  -11.7528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8129  -10.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5200  -10.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2283  -10.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5187   -9.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8142  -11.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5225  -12.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5197  -12.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2272  -13.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9352  -12.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9313  -12.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2232  -11.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9354  -10.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6437  -10.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1493   -9.3029    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  6
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 23  1  0
 23 24  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289692

   ethyl (2S)-2-[[(E)-3-(4-chlorophenyl)prop-2-enoyl]amino]-3-phenylpropanoate

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: 357.84

Molecular Weight (Monoisotopic): 357.1132

AlogP: 3.64

#Rotatable Bonds: 7

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.62

CX Basic pKa: ┄

CX LogP: 4.36

CX LogD: 4.36

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.47

References

1. ZHU J, KOBAMOTO N, YASUDA M, TAWATA S.  (2000)  Synthesis and Fungitoxic Activity of N-Cinnamoyl--Amino Acid Esters,  25  (3): [10.1584/jpestics.25.259]

Source

Source(1):

• Scientific Literature