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

ID: ALA2289668

PubChem CID: 76316604

Max Phase: Preclinical

Molecular Formula: C16H19Cl2NO3

Molecular Weight: 344.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H19Cl2NO3/c1-10(2)8-14(16(21)22-3)19-15(20)7-5-11-4-6-12(17)9-13(11)18/h4-7,9-10,14H,8H2,1-3H3,(H,19,20)/b7-5+/t14-/m0/s1

Standard InChI Key:  ZRUJGTRYHMYESH-DYLGSBMWSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   17.4568  -17.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4556  -18.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1637  -19.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8733  -18.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8705  -17.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1619  -17.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5817  -19.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2887  -18.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9971  -19.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7042  -18.6690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9984  -19.8959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4125  -19.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1196  -18.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8279  -19.0742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1183  -17.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4138  -19.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1221  -20.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1234  -21.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8292  -19.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5350  -18.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7490  -17.4459    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.5767  -17.4395    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  1  0
 17 19  1  0
 14 20  1  0
  1 21  1  0
  5 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289668

   methyl (2S)-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4-methylpentanoate

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: 12.24

CX Basic pKa: ┄

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.63

Np Likeness Score: -0.63

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