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

ID: ALA2289672

PubChem CID: 76309377

Max Phase: Preclinical

Molecular Formula: C16H19Cl2NO3

Molecular Weight: 344.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H19Cl2NO3/c1-4-10(2)15(16(21)22-3)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+/t10-,15-/m0/s1

Standard InChI Key:  SHDGCTPJOCMNSI-MCCLBDCCSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   10.6840  -22.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6828  -23.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3909  -23.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1005  -23.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0977  -22.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3891  -21.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8089  -23.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5160  -23.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2243  -23.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9314  -23.1842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2256  -24.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6397  -23.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3468  -23.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0551  -23.5894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3455  -22.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6410  -24.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9339  -24.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3493  -24.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3506  -25.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0564  -24.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9762  -21.9611    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.8039  -21.9547    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
 12 10  1  6
 12 13  1  0
 13 14  1  0
 13 15  2  0
 12 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 14 20  1  0
  1 21  1  0
  5 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289672

   methyl (2S,3S)-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-3-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: 12.18

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 4.29

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