4-Trifluoromethyl-(E)-cinnamoyl-L-isoleucine Acid

ID: ALA5081853

PubChem CID: 166629804

Max Phase: Preclinical

Molecular Formula: C17H20F3NO3

Molecular Weight: 343.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)/C=C/c1ccc(C(F)(F)F)cc1)C(=O)OC

Standard InChI:  InChI=1S/C17H20F3NO3/c1-4-11(2)15(16(23)24-3)21-14(22)10-7-12-5-8-13(9-6-12)17(18,19)20/h5-11,15H,4H2,1-3H3,(H,21,22)/b10-7+/t11-,15-/m0/s1

Standard InChI Key:  QYBIHGYLUJIPFN-HSSPRWGWSA-N

Molfile:  

 
     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   36.1294   -3.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8439   -3.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4149   -3.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7005   -3.6709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4149   -2.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5583   -3.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5558   -4.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2695   -4.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9848   -4.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9822   -3.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2680   -3.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9860   -3.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9860   -2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2715   -2.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2715   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7005   -2.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2715   -3.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2715   -4.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5544   -4.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6999   -4.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5571   -3.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3565   -5.2815    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   39.8447   -5.7579    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   40.5114   -4.5996    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  1  0
  3  5  2  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 12  4  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 12 17  1  0
 17 18  1  0
 18 19  1  0
  9 20  1  0
 17 21  1  6
 20 22  1  0
 20 23  1  0
 20 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5081853

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 343.35

Molecular Weight (Monoisotopic): 343.1395

AlogP: 3.42

#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: 12.24

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: -0.40

References

1. Hu XL, Lv XY, Wang R, Long H, Feng JH, Wang BL, Shen W, Liu H, Xiong F, Zhang XQ, Ye WC, Wang H..  (2021)  Optimization of N-Phenylpropenoyl-l-amino Acids as Potent and Selective Inducible Nitric Oxide Synthase Inhibitors for Parkinson's Disease.,  64  (11.0): [PMID:34019417] [10.1021/acs.jmedchem.1c00578]

Source

Source(1):

• Scientific Literature