(S)-methyl 2-(3-(4-chlorophenyl)acrylamido)-3-phenylpropanoate

ID: ALA2289691

PubChem CID: 41498861

Max Phase: Preclinical

Molecular Formula: C19H18ClNO3

Molecular Weight: 343.81

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H18ClNO3/c1-24-19(23)17(13-15-5-3-2-4-6-15)21-18(22)12-9-14-7-10-16(20)11-8-14/h2-12,17H,13H2,1H3,(H,21,22)/b12-9+/t17-/m0/s1

Standard InChI Key:  GFFVINCQFWDHTA-KQPPXVQYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   26.0414   -9.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0403  -10.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7483  -10.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4580  -10.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4551   -9.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7465   -9.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1663  -10.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8734  -10.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5817  -10.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2888  -10.4021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.5830  -11.6290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9971  -10.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7042  -10.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4126  -10.8074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7029   -9.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9984  -11.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7068  -12.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7039  -12.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4114  -13.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1195  -12.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1155  -12.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4075  -11.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1196  -10.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3336   -9.1791    0.0000 Cl  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  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 23  1  0
  1 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289691

   methyl (2S)-2-[[(E)-3-(4-chlorophenyl)prop-2-enoyl]amino]-3-phenylpropanoate

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: 343.81

Molecular Weight (Monoisotopic): 343.0975

AlogP: 3.25

#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: 12.55

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 4.01

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.65

Np Likeness Score: -0.34

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]

2. 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