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

ID: ALA1909824

PubChem CID: 56930208

Max Phase: Preclinical

Molecular Formula: C17H16Br2N2O3

Molecular Weight: 456.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(C)c(COc2c(Br)cc(Br)cc2/C=C/C(=O)O)nc1C

Standard InChI:  InChI=1S/C17H16Br2N2O3/c1-9-10(2)21-15(11(3)20-9)8-24-17-12(4-5-16(22)23)6-13(18)7-14(17)19/h4-7H,8H2,1-3H3,(H,22,23)/b5-4+

Standard InChI Key:  MLLWBSNBCHQQKC-SNAWJCMRSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    2.1462    1.6351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4232    0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8635    2.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346    2.0525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -0.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7001   -0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6944   -1.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4060   -2.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233   -1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1290   -0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0057    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7173    0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116    1.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4346    0.4224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232    2.0724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1405    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    0.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8635    0.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8521    2.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349   -2.0823    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0229   -2.0625    0.0000 Br  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
  8 24  1  0
  3  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1909824

   (E)-3-[3,5-dibromo-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: 456.13

Molecular Weight (Monoisotopic): 453.9528

AlogP: 4.60

#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: 2.27

CX Basic pKa: 1.54

CX LogP: 2.89

CX LogD: -0.24

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: -0.34

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