4-trifluoromethyl-(E)-cinnamoyl-L-phenylalanine acid

ID: ALA5090551

PubChem CID: 26705259

Max Phase: Preclinical

Molecular Formula: C20H18F3NO3

Molecular Weight: 377.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](Cc1ccccc1)NC(=O)/C=C/c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C20H18F3NO3/c1-27-19(26)17(13-15-5-3-2-4-6-15)24-18(25)12-9-14-7-10-16(11-8-14)20(21,22)23/h2-12,17H,13H2,1H3,(H,24,25)/b12-9+/t17-/m0/s1

Standard InChI Key:  PJZCZRFHBQFJGK-KQPPXVQYSA-N

Molfile:  

 
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   26.6371   -2.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2081   -2.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4936   -3.1752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2081   -1.9377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3516   -3.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.0628   -4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7782   -4.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7756   -3.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0614   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7791   -2.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7791   -1.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0645   -1.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0645   -0.7001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4936   -1.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0645   -3.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0645   -4.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3474   -4.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3471   -5.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0621   -5.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7791   -5.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7758   -4.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4933   -4.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1500   -4.7859    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.6381   -5.2624    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.3049   -4.1039    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
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 12 17  1  0
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 18 19  2  0
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 21 22  1  0
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  9 24  1  0
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 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5090551

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

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: 377.36

Molecular Weight (Monoisotopic): 377.1239

AlogP: 3.62

#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: 12.22

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -0.44

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