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

ID: ALA2289704

Cas Number: 127750-57-6

PubChem CID: 6449722

Max Phase: Preclinical

Molecular Formula: C15H19NO3

Molecular Weight: 261.32

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H19NO3/c1-11(2)14(15(18)19-3)16-13(17)10-9-12-7-5-4-6-8-12/h4-11,14H,1-3H3,(H,16,17)/b10-9+/t14-/m0/s1

Standard InChI Key:  FPCRRVNOCVWNIW-HBWSCVEGSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    0.5723   -4.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711   -5.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -5.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888   -5.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9860   -4.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2774   -4.1558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6972   -5.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -5.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1126   -5.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8197   -5.3793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1139   -6.6062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5280   -5.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2351   -5.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9434   -5.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2338   -4.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293   -6.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222   -7.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2376   -7.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9447   -6.6018    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
M  END

Alternative Forms

1. Parent:

   

   ALA2289704

   N-Cinnamoyl-D,L-valine methyl ester

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: 2.01

#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: 13.04

CX Basic pKa: ┄

CX LogP: 2.63

CX LogD: 2.63

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.65

Np Likeness Score: -0.10

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