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

ID: ALA2289673

PubChem CID: 76313087

Max Phase: Preclinical

Molecular Formula: C17H21Cl2NO3

Molecular Weight: 358.26

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H21Cl2NO3/c1-4-11(3)16(17(22)23-5-2)20-15(21)9-7-12-6-8-13(18)10-14(12)19/h6-11,16H,4-5H2,1-3H3,(H,20,21)/b9-7+/t11-,16-/m0/s1

Standard InChI Key:  SKFUADZAAQFHGQ-WJLVXLOQSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   17.4444  -22.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4432  -22.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1513  -23.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8609  -22.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8581  -22.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1495  -21.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5693  -23.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2764  -22.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9847  -23.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6918  -22.9943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9860  -24.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4001  -23.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1072  -22.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8155  -23.3996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1059  -22.1749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4014  -24.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6943  -24.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1097  -24.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1110  -25.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5226  -22.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2309  -23.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7366  -21.7713    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.5643  -21.7648    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
 20 21  1  0
  1 22  1  0
  5 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289673

   ethyl (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: 358.26

Molecular Weight (Monoisotopic): 357.0898

AlogP: 4.10

#Rotatable Bonds: 7

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: 12.26

CX Basic pKa: ┄

CX LogP: 4.64

CX LogD: 4.64

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: -0.78

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