(R)-2-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)-3-(4-hydroxyphenyl)propanoic acid

ID: ALA5092908

PubChem CID: 166631528

Max Phase: Preclinical

Molecular Formula: C19H19NO6

Molecular Weight: 357.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)N[C@H](Cc2ccc(O)cc2)C(=O)O)ccc1O

Standard InChI:  InChI=1S/C19H19NO6/c1-26-17-11-13(4-8-16(17)22)5-9-18(23)20-15(19(24)25)10-12-2-6-14(21)7-3-12/h2-9,11,15,21-22H,10H2,1H3,(H,20,23)(H,24,25)/b9-5+/t15-/m1/s1

Standard InChI Key:  RWAXPZCUFIKMTQ-FUVBFXSKSA-N

Molfile:  

 
     RDKit          2D

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   33.8482   -9.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8470  -10.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5619  -10.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2782  -10.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2754   -9.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5600   -9.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1322  -10.8016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1337   -9.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1335   -8.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9884   -9.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7043   -9.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4173   -9.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1332   -9.5480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.4141   -8.3132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8462   -9.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5621   -9.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8430   -8.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5560   -7.8926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1271   -7.8980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5653  -10.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8514  -10.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8541  -11.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5707  -12.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2860  -11.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2797  -10.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5750  -12.8410    0.0000 O   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
  2  7  1  0
  1  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 15 13  1  1
 15 16  1  0
 15 17  1  0
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 17 19  2  0
 16 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5092908

   ---

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: 357.36

Molecular Weight (Monoisotopic): 357.1212

AlogP: 1.93

#Rotatable Bonds: 7

Polar Surface Area: 116.09

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.39

CX Basic pKa: ┄

CX LogP: 2.49

CX LogD: -0.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: 0.47

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