(E)-3-(5-chloro-2-((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)acrylic acid

ID: ALA1909717

PubChem CID: 56930207

Max Phase: Preclinical

Molecular Formula: C17H17ClN2O3

Molecular Weight: 332.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(C)c(COc2ccc(Cl)cc2/C=C/C(=O)O)nc1C

Standard InChI:  InChI=1S/C17H17ClN2O3/c1-10-11(2)20-15(12(3)19-10)9-23-16-6-5-14(18)8-13(16)4-7-17(21)22/h4-8H,9H2,1-3H3,(H,21,22)/b7-4+

Standard InChI Key:  DGIBHBWMBPUJSV-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    2.5006    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  1  0
 14 15  1  0
 14 16  2  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 16 19  1  0
 19 20  1  0
 18 21  1  0
 15 22  1  0
 13 14  1  0
  7 12  1  0
 10 23  1  0
  3  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1909717

   (E)-3-[5-chloro-2-[(3,5,6-trimethylpyrazin-2-yl)methoxy]phenyl]prop-2-enoic acid

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: 332.79

Molecular Weight (Monoisotopic): 332.0928

AlogP: 3.73

#Rotatable Bonds: 5

Polar Surface Area: 72.31

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.21

CX Basic pKa: 1.65

CX LogP: 2.16

CX LogD: -1.10

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.74

References

1. Chen H, Li G, Zhan P, Liu X..  (2011)  Ligustrazine derivatives. Part 5: design, synthesis and biological evaluation of novel ligustrazinyloxy-cinnamic acid derivatives as potent cardiovascular agents.,  46  (11): [PMID:21993151] [10.1016/j.ejmech.2011.09.030]

Source

Source(1):

• Scientific Literature