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

ID: ALA1909716

PubChem CID: 56930206

Max Phase: Preclinical

Molecular Formula: C18H20N2O4

Molecular Weight: 328.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(/C=C/C(=O)O)c1OCc1nc(C)c(C)nc1C

Standard InChI:  InChI=1S/C18H20N2O4/c1-11-12(2)20-15(13(3)19-11)10-24-18-14(8-9-17(21)22)6-5-7-16(18)23-4/h5-9H,10H2,1-4H3,(H,21,22)/b9-8+

Standard InChI Key:  ZNLJDMTXMRHGRE-CMDGGOBGSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -3.9297   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7863    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863   -1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3573   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.0626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  7  8  1  0
  5  9  1  0
  4 10  1  0
 11 12  2  0
 12 13  1  0
 13 22  2  0
 22 14  1  0
 14 15  2  0
 15 11  1  0
 14 16  1  0
 16 10  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 15  1  0
 22 24  1  0
 24 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1909716

   (E)-3-[3-methoxy-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: 328.37

Molecular Weight (Monoisotopic): 328.1423

AlogP: 3.09

#Rotatable Bonds: 6

Polar Surface Area: 81.54

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.23

CX Basic pKa: 1.65

CX LogP: 1.40

CX LogD: -1.86

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: -0.31

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