(S)-propyl 2-(3-(2,4-dichlorophenyl)acrylamido)propanoate

ID: ALA2289695

PubChem CID: 76323963

Max Phase: Preclinical

Molecular Formula: C15H17Cl2NO3

Molecular Weight: 330.21

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H17Cl2NO3/c1-3-8-21-15(20)10(2)18-14(19)7-5-11-4-6-12(16)9-13(11)17/h4-7,9-10H,3,8H2,1-2H3,(H,18,19)/b7-5+/t10-/m0/s1

Standard InChI Key:  XUQAKBXWGIKDSW-STUBTGCMSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   18.0841  -14.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0830  -15.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7910  -15.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5007  -15.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4978  -14.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7892  -13.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2090  -15.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9161  -15.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6244  -15.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3315  -15.1278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6257  -16.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0398  -15.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7469  -15.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4553  -15.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7456  -14.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0411  -16.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1623  -15.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8707  -15.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8720  -16.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3763  -13.9048    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.2040  -13.8983    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
 14 17  1  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  5 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289695

   propyl (2S)-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]propanoate

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: 3.46

#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: 12.23

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.64

Np Likeness Score: -1.04

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