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

ID: ALA2288837

PubChem CID: 6474706

Max Phase: Preclinical

Molecular Formula: C18H20N2O3

Molecular Weight: 312.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H20N2O3/c1-12(2)8-14-10-20-15(11-19-14)16(21)6-4-13-5-7-17(22)18(9-13)23-3/h4-7,9-12,22H,8H2,1-3H3/b6-4+

Standard InChI Key:  LWJHFQDVCFXRKC-GQCTYLIASA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   18.3978   -1.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3966   -2.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1047   -3.1765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8143   -2.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8115   -1.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1029   -1.5392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5177   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2269   -1.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5146   -0.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9331   -1.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6423   -1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6423   -2.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3507   -3.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0578   -2.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0521   -1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3432   -1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7568   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4675   -1.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7676   -3.1493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6886   -3.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6879   -3.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9799   -4.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3953   -4.4019    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
 21 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288837

   1-(5-Isobutyl-2-pyrazinyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-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: 312.37

Molecular Weight (Monoisotopic): 312.1474

AlogP: 3.29

#Rotatable Bonds: 6

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: 2.94

CX LogD: 2.94

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: 0.09

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