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

ID: ALA5082466

PubChem CID: 32043730

Max Phase: Preclinical

Molecular Formula: C17H20F3NO3

Molecular Weight: 343.35

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H20F3NO3/c1-11(2)10-14(16(23)24-3)21-15(22)9-6-12-4-7-13(8-5-12)17(18,19)20/h4-9,11,14H,10H2,1-3H3,(H,21,22)/b9-6+/t14-/m0/s1

Standard InChI Key:  AGUBOQWDONYLFR-MRZGDXHCSA-N

Molfile:  

 
     RDKit          2D

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   25.7001  -17.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4147  -16.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9856  -16.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2712  -17.1627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9856  -15.9251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1291  -17.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1265  -17.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8402  -18.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5557  -17.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5530  -17.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8388  -16.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5567  -16.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5567  -15.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8422  -15.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8422  -14.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2712  -15.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8422  -17.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8422  -17.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1253  -18.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5536  -18.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2706  -18.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9274  -18.7732    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.4154  -19.2497    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.0822  -18.0912    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
 20 18  1  0
  9 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5082466

   methyl (2S)-4-methyl-2-[[(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl]amino]pentanoate

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: 12.30

CX Basic pKa: ┄

CX LogP: 3.88

CX LogD: 3.88

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