(S)-ethyl 2-cinnamamido-4-methylpentanoate

ID: ALA2289707

PubChem CID: 76327513

Max Phase: Preclinical

Molecular Formula: C17H23NO3

Molecular Weight: 289.38

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H23NO3/c1-4-21-17(20)15(12-13(2)3)18-16(19)11-10-14-8-6-5-7-9-14/h5-11,13,15H,4,12H2,1-3H3,(H,18,19)/b11-10+/t15-/m0/s1

Standard InChI Key:  ZWSOBWXBKQTVBH-NKSUMMKUSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   24.5432   -4.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5421   -5.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2501   -5.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9598   -5.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9569   -4.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2483   -4.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6681   -5.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3752   -5.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0835   -5.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7906   -5.2596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0848   -6.4865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4990   -5.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2060   -5.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9144   -5.6649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2047   -4.4402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5002   -6.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2086   -6.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2099   -7.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9156   -6.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6214   -5.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3298   -5.6627    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
 17 18  1  0
 17 19  1  0
 14 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289707

   ethyl (2S)-4-methyl-2-[[(E)-3-phenylprop-2-enoyl]amino]pentanoate

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: 289.38

Molecular Weight (Monoisotopic): 289.1678

AlogP: 2.79

#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: 13.19

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.62

Np Likeness Score: -0.20

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