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

ID: ALA2289667

PubChem CID: 76309374

Max Phase: Preclinical

Molecular Formula: C16H19Cl2NO3

Molecular Weight: 344.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H19Cl2NO3/c1-4-22-16(21)15(10(2)3)19-14(20)8-6-11-5-7-12(17)9-13(11)18/h5-10,15H,4H2,1-3H3,(H,19,20)/b8-6+/t15-/m0/s1

Standard InChI Key:  GHGRMOSTTRGVEN-VFADXPBXSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    9.2229  -18.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2218  -18.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9298  -19.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6395  -18.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6367  -18.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9280  -17.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3478  -19.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0549  -18.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7633  -19.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4703  -18.9496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7645  -20.1765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1787  -19.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8857  -18.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5941  -19.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8845  -18.1302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1800  -20.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4729  -20.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8883  -20.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3012  -18.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0095  -19.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5151  -17.7266    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3428  -17.7201    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
 16 18  1  0
 14 19  1  0
 19 20  1  0
  1 21  1  0
  5 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289667

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

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: 344.24

Molecular Weight (Monoisotopic): 343.0742

AlogP: 3.71

#Rotatable Bonds: 6

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: 12.18

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: -0.89

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