(S)-methyl 2-cinnamamidopropanoate

ID: ALA2289699

PubChem CID: 40452656

Max Phase: Preclinical

Molecular Formula: C13H15NO3

Molecular Weight: 233.27

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C13H15NO3/c1-10(13(16)17-2)14-12(15)9-8-11-6-4-3-5-7-11/h3-10H,1-2H3,(H,14,15)/b9-8+/t10-/m0/s1

Standard InChI Key:  PEGDZUDNIIQFJI-DDXVTDLHSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.6094   -1.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6083   -1.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -2.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260   -1.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0231   -1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3145   -0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4414   -1.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497   -2.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8568   -1.8670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1510   -3.0939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5652   -2.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2722   -1.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9806   -2.2723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2709   -1.0476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5664   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9819   -3.0895    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
M  END

Alternative Forms

1. Parent:

   

   ALA2289699

   methyl (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: 233.27

Molecular Weight (Monoisotopic): 233.1052

AlogP: 1.38

#Rotatable Bonds: 4

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: 13.05

CX Basic pKa: ┄

CX LogP: 1.75

CX LogD: 1.75

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.63

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