(S)-propyl 2-cinnamamidopropanoate

ID: ALA2289701

PubChem CID: 76313091

Max Phase: Preclinical

Molecular Formula: C15H19NO3

Molecular Weight: 261.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H19NO3/c1-3-11-19-15(18)12(2)16-14(17)10-9-13-7-5-4-6-8-13/h4-10,12H,3,11H2,1-2H3,(H,16,17)/b10-9+/t12-/m0/s1

Standard InChI Key:  HAEDWFPJATYBGS-VMPCVLLUSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   16.9078   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9067   -1.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6147   -2.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3244   -1.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3216   -0.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6130   -0.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0327   -2.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7398   -1.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4482   -2.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1552   -1.6607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4494   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8636   -2.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5706   -1.6584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2790   -2.0659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5694   -0.8413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8649   -2.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9861   -1.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6944   -2.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6957   -2.8809    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
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289701

   propyl (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: 261.32

Molecular Weight (Monoisotopic): 261.1365

AlogP: 2.16

#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: 13.17

CX Basic pKa: ┄

CX LogP: 2.62

CX LogD: 2.62

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.63

Np Likeness Score: -0.46

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