(S)-ethyl 2-cinnamamido-3-methylbutanoate

ID: ALA2289705

PubChem CID: 76309380

Max Phase: Preclinical

Molecular Formula: C16H21NO3

Molecular Weight: 275.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H21NO3/c1-4-20-16(19)15(12(2)3)17-14(18)11-10-13-8-6-5-7-9-13/h5-12,15H,4H2,1-3H3,(H,17,18)/b11-10+/t15-/m0/s1

Standard InChI Key:  IPQWBQMJQGUOOD-NKSUMMKUSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    8.0467   -4.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0455   -5.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7536   -5.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4632   -5.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4604   -4.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7518   -4.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1716   -5.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8787   -5.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5870   -5.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2941   -5.4825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5883   -6.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0024   -5.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7095   -5.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4178   -5.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7082   -4.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0037   -6.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2966   -7.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7120   -7.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1249   -5.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8332   -5.8855    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
 16 17  1  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289705

   ethyl (2S)-3-methyl-2-[[(E)-3-phenylprop-2-enoyl]amino]butanoate

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: 275.35

Molecular Weight (Monoisotopic): 275.1521

AlogP: 2.40

#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: 13.09

CX Basic pKa: ┄

CX LogP: 2.99

CX LogD: 2.99

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: -0.32

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