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

ID: ALA2289706

Cas Number: 127852-93-1

PubChem CID: 6449731

Max Phase: Preclinical

Molecular Formula: C16H21NO3

Molecular Weight: 275.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H21NO3/c1-12(2)11-14(16(19)20-3)17-15(18)10-9-13-7-5-4-6-8-13/h4-10,12,14H,11H2,1-3H3,(H,17,18)/b10-9+/t14-/m0/s1

Standard InChI Key:  OXFYLVKTVPTJPQ-HBWSCVEGSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   16.2805   -4.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2794   -5.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9874   -5.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6971   -5.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6942   -4.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9856   -3.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4054   -5.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1125   -5.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8208   -5.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5279   -5.2018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8221   -6.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2362   -5.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9433   -5.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6517   -5.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9420   -4.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2375   -6.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9459   -6.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9472   -7.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6529   -6.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3587   -5.1974    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
M  END

Alternative Forms

1. Parent:

   

   ALA2289706

   trans-N-Cinnamoyl-D,L-leucine 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: 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: 13.14

CX Basic pKa: ┄

CX LogP: 3.00

CX LogD: 3.00

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: -0.03

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