Entacapone

ID: ALA3770406

PubChem CID: 56646803

Max Phase: Preclinical

Molecular Formula: C15H16N2O5

Molecular Weight: 304.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(CC)C(=O)/C(C#N)=C/c1cc(O)c(O)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C15H16N2O5/c1-3-10(4-2)14(19)11(8-16)5-9-6-12(17(21)22)15(20)13(18)7-9/h5-7,10,18,20H,3-4H2,1-2H3/b11-5+

Standard InChI Key:  HERFVBIZLLFZOL-VZUCSPMQSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432    3.5993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -6.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913   -7.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1877   -7.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -3.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2538   -4.3503    0.0000 N   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
  7  8  2  0
  7  9  1  0
  3  7  1  0
  1 10  1  0
  2 11  1  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 17 20  1  0
 21 22  3  0
 13 21  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3770406

   (2E)-2-[(3,4-dihydroxy-5-nitrophenyl)methylidene]-4-ethyl-3-oxohexanenitrile

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: 304.30

Molecular Weight (Monoisotopic): 304.1059

AlogP: 2.92

#Rotatable Bonds: 6

Polar Surface Area: 124.46

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.72

CX Basic pKa: ┄

CX LogP: 3.74

CX LogD: 2.22

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.27

Np Likeness Score: -0.31

References

1. Zhang H, Tong R, Bai L, Shi J, Ouyang L..  (2016)  Emerging targets and new small molecule therapies in Parkinson's disease treatment.,  24  (7): [PMID:26935940] [10.1016/j.bmc.2016.02.030]

Source

Source(1):

• Scientific Literature