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

ID: ALA2288597

PubChem CID: 6474716

Max Phase: Preclinical

Molecular Formula: C17H18N2O2

Molecular Weight: 282.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Cc1cnc(C(=O)/C=C/c2ccc(O)cc2)cn1

Standard InChI:  InChI=1S/C17H18N2O2/c1-12(2)9-14-10-19-16(11-18-14)17(21)8-5-13-3-6-15(20)7-4-13/h3-8,10-12,20H,9H2,1-2H3/b8-5+

Standard InChI Key:  YUXBARAKKNGZSH-VMPITWQZSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   18.5257  -10.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5246  -11.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2326  -12.1491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9423  -11.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9394  -10.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2308  -10.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6456  -10.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3549  -10.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6425   -9.6886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0610  -10.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7703  -10.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7702  -11.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4787  -12.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1858  -11.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1801  -10.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4711  -10.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8956  -12.1219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8165  -12.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8159  -12.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1079  -13.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5233  -13.3745    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
 14 17  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288597

   1-(5-Isobutyl-2-pyrazinyl)-3-(4-hydroxyphenyl)-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: 282.34

Molecular Weight (Monoisotopic): 282.1368

AlogP: 3.28

#Rotatable Bonds: 5

Polar Surface Area: 63.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: ┄

CX LogP: 3.10

CX LogD: 3.09

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: -0.03

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