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

ID: ALA2289698

PubChem CID: 76320325

Max Phase: Preclinical

Molecular Formula: C15H17Cl2NO3

Molecular Weight: 330.21

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H17Cl2NO3/c1-9(2)14(15(20)21-3)18-13(19)7-5-10-4-6-11(16)8-12(10)17/h4-9,14H,1-3H3,(H,18,19)/b7-5+/t14-/m0/s1

Standard InChI Key:  ACQAJYXTXXWPDF-DYLGSBMWSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
    1.7485  -18.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474  -18.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4554  -19.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1651  -18.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1623  -18.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536  -17.6230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8734  -19.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5805  -18.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2889  -19.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959  -18.8464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2901  -20.0733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043  -19.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4113  -18.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1197  -19.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4101  -18.0270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7056  -20.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985  -20.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4139  -20.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1210  -20.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407  -17.6234    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8684  -17.6170    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
  1 20  1  0
  5 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289698

   methyl (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: 330.21

Molecular Weight (Monoisotopic): 329.0585

AlogP: 3.32

#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: 12.10

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: -0.72

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