(S)-ethyl 2-cinnamamidopropanoate

ID: ALA2289700

PubChem CID: 76316607

Max Phase: Preclinical

Molecular Formula: C14H17NO3

Molecular Weight: 247.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](C)NC(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C14H17NO3/c1-3-18-14(17)11(2)15-13(16)10-9-12-7-5-4-6-8-12/h4-11H,3H2,1-2H3,(H,15,16)/b10-9+/t11-/m0/s1

Standard InChI Key:  GQTHELNVGNQBHO-USKTWTLRSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    8.8597   -0.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8586   -1.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5666   -2.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2763   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2735   -0.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5649   -0.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9847   -2.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6917   -1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4001   -2.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1071   -1.7845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4014   -3.0114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8155   -2.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5225   -1.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2309   -2.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5213   -0.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8168   -3.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9380   -1.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6463   -2.1875    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA2289700

   ethyl (2S)-2-[[(E)-3-phenylprop-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: 247.29

Molecular Weight (Monoisotopic): 247.1208

AlogP: 1.77

#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: 13.12

CX Basic pKa: ┄

CX LogP: 2.10

CX LogD: 2.10

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.64

Np Likeness Score: -0.51

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