(S)-ethyl 2-(3-(2,4-dichlorophenyl)acrylamido)propanoate

ID: ALA2289694

PubChem CID: 76309379

Max Phase: Preclinical

Molecular Formula: C14H15Cl2NO3

Molecular Weight: 316.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](C)NC(=O)/C=C/c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C14H15Cl2NO3/c1-3-20-14(19)9(2)17-13(18)7-5-10-4-6-11(15)8-12(10)16/h4-9H,3H2,1-2H3,(H,17,18)/b7-5+/t9-/m0/s1

Standard InChI Key:  WXRKJHVLNPHQEZ-IWGCBNPKSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   10.0360  -14.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0349  -15.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7429  -15.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4526  -15.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4497  -14.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7411  -14.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1609  -15.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8680  -15.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5763  -15.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2834  -15.2516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5776  -16.4785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9917  -15.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6988  -15.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4072  -15.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6975  -14.4322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9930  -16.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1142  -15.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8226  -15.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3282  -14.0286    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.1559  -14.0221    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
 14 17  1  0
 17 18  1  0
  1 19  1  0
  5 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289694

   ethyl (2S)-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]propanoate

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: 316.18

Molecular Weight (Monoisotopic): 315.0429

AlogP: 3.07

#Rotatable Bonds: 5

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: 12.13

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.31

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.67

Np Likeness Score: -1.12

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