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

ID: ALA5093141

PubChem CID: 166631182

Max Phase: Preclinical

Molecular Formula: C16H20FNO3

Molecular Weight: 293.34

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H20FNO3/c1-4-11(2)15(16(20)21-3)18-14(19)10-7-12-5-8-13(17)9-6-12/h5-11,15H,4H2,1-3H3,(H,18,19)/b10-7+/t11-,15-/m0/s1

Standard InChI Key:  XAXBNJJTIITAMV-HSSPRWGWSA-N

Molfile:  

 
     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   16.2043   -4.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9187   -3.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4898   -3.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7753   -4.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4898   -2.9626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6332   -4.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6307   -5.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3443   -5.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0597   -5.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0571   -4.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3429   -3.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0609   -3.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0609   -2.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3464   -2.5501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3464   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7753   -2.5501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3464   -4.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3464   -5.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6293   -5.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7748   -5.4375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.6318   -3.7876    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA5093141

   ---

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: 293.34

Molecular Weight (Monoisotopic): 293.1427

AlogP: 2.54

#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: 12.62

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.65

Np Likeness Score: -0.39

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