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

ID: ALA2288838

PubChem CID: 6474707

Max Phase: Preclinical

Molecular Formula: C18H20N2O3

Molecular Weight: 312.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1cnc(C(=O)/C=C/c2ccc(O)c(OC)c2)cn1

Standard InChI:  InChI=1S/C18H20N2O3/c1-3-4-5-14-11-20-15(12-19-14)16(21)8-6-13-7-9-17(22)18(10-13)23-2/h6-12,22H,3-5H2,1-2H3/b8-6+

Standard InChI Key:  TWUVVIIJHPCWPI-SOFGYWHQSA-N

Molfile:  

     RDKit          2D

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   26.5532   -2.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5520   -2.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2601   -3.2302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9697   -2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9669   -1.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2583   -1.5928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6731   -1.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3823   -1.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6700   -0.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0885   -1.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7977   -1.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7977   -2.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5061   -3.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2133   -2.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2075   -1.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4986   -1.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9122   -1.5628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6229   -1.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9230   -3.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8440   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8433   -4.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1353   -4.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4279   -4.0453    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
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288838

   1-(5-Butyl-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: 3.43

#Rotatable Bonds: 7

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: 0.02

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: 0.11

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