(E)-3-(4-hydroxy-3-methoxyphenyl)-1-(5-isopropylpyrazin-2-yl)prop-2-en-1-one

ID: ALA2288836

PubChem CID: 76323910

Max Phase: Preclinical

Molecular Formula: C17H18N2O3

Molecular Weight: 298.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)c2cnc(C(C)C)cn2)ccc1O

Standard InChI:  InChI=1S/C17H18N2O3/c1-11(2)13-9-19-14(10-18-13)15(20)6-4-12-5-7-16(21)17(8-12)22-3/h4-11,21H,1-3H3/b6-4+

Standard InChI Key:  PLIJYQYRUQERLT-GQCTYLIASA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    9.7347   -1.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7336   -2.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4416   -3.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1513   -2.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1484   -1.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4398   -1.5722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8546   -1.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5639   -1.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8515   -0.7490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2700   -1.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9793   -1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9792   -2.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6877   -3.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3948   -2.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3891   -1.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6801   -1.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0938   -1.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8045   -1.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1046   -3.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0255   -3.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3182   -2.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249   -4.0258    0.0000 C   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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
 17 18  1  0
 14 19  1  0
  2 20  1  0
 20 21  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288836

   (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(5-propan-2-ylpyrazin-2-yl)prop-2-en-1-one

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: 3.21

#Rotatable Bonds: 5

Polar Surface Area: 72.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.50

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: 0.22

References

1. Opletalová V, Hartl J, Patel A, Palát K, Buchta V..  (2002)  Ring substituted 3-phenyl-1-(2-pyrazinyl)-2-propen-1-ones as potential photosynthesis-inhibiting, antifungal and antimycobacterial agents.,  57  (2): [PMID:11902656] [10.1016/s0014-827x(01)01187-9]

Source

Source(1):

• Scientific Literature