3-Hydroxy-2-(5'-phenylpent-4'E-enoyl)cyclohex-2-en-1-one

ID: ALA3289507

PubChem CID: 90681779

Max Phase: Preclinical

Molecular Formula: C17H18O3

Molecular Weight: 270.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC/C=C/c1ccccc1)C1=C(O)CCCC1=O

Standard InChI:  InChI=1S/C17H18O3/c18-14(17-15(19)11-6-12-16(17)20)10-5-4-9-13-7-2-1-3-8-13/h1-4,7-9,19H,5-6,10-12H2/b9-4+

Standard InChI Key:  YRVZWDMWLRTUJA-RUDMXATFSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    7.9835   -7.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9835   -7.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2690   -8.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5545   -7.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5545   -7.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2690   -6.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6979   -6.7396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6979   -8.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4124   -7.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1269   -8.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8413   -7.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5558   -8.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6979   -9.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2703   -7.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2703   -7.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9848   -6.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6992   -7.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6992   -7.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9848   -8.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2690   -9.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  1  7  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
  8 13  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 12 14  1  0
  2  8  1  0
  3 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3289507

   2-[(E)-1-hydroxy-5-phenylpent-4-enylidene]cyclohexane-1,3-dione

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: 270.33

Molecular Weight (Monoisotopic): 270.1256

AlogP: 3.61

#Rotatable Bonds: 5

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.99

CX Basic pKa: ┄

CX LogP: 3.46

CX LogD: 1.08

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.83

Np Likeness Score: 1.05

References

1. Ferreira EA, Reigada JB, Correia MV, Young MC, Guimarães EF, Franchi GC, Nowill AE, Lago JH, Yamaguchi LF, Kato MJ..  (2014)  Antifungal and cytotoxic 2-acylcyclohexane-1,3-diones from Peperomia alata and P. trineura.,  77  (6): [PMID:24905499] [10.1021/np500130x]

Source

Source(1):

• Scientific Literature