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

ID: ALA1909714

PubChem CID: 53252929

Max Phase: Preclinical

Molecular Formula: C17H18N2O3

Molecular Weight: 298.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(C)c(COc2cccc(/C=C/C(=O)O)c2)nc1C

Standard InChI:  InChI=1S/C17H18N2O3/c1-11-12(2)19-16(13(3)18-11)10-22-15-6-4-5-14(9-15)7-8-17(20)21/h4-9H,10H2,1-3H3,(H,20,21)/b8-7+

Standard InChI Key:  IZPWNABEFBTKEV-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -0.7144   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0025   -1.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194   -1.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0025    0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4288    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577    1.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745    1.4479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2915    1.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2915    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5745   -0.2077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0059    1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0059   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8626    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5770   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8626    1.0312    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
  1  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 14 17  1  0
 11 18  1  0
  5  7  1  0
  7 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1909714

   (E)-3-[3-[(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: 298.34

Molecular Weight (Monoisotopic): 298.1317

AlogP: 3.08

#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: 3.52

CX Basic pKa: 1.60

CX LogP: 1.55

CX LogD: -1.64

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.86

Np Likeness Score: -0.44

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