3-Hydroxy-2-(11'-phenylundec-10'E-enoyl)cyclohex-2-en-1-one

ID: ALA3289508

PubChem CID: 90681780

Max Phase: Preclinical

Molecular Formula: C23H30O3

Molecular Weight: 354.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H30O3/c24-20(23-21(25)17-12-18-22(23)26)16-11-6-4-2-1-3-5-8-13-19-14-9-7-10-15-19/h7-10,13-15,25H,1-6,11-12,16-18H2/b13-8+

Standard InChI Key:  HFFNMSOTVGPTQS-MDWZMJQESA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   14.7709   -8.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0565   -7.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0565   -7.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7709   -6.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4854   -7.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4854   -7.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7709   -9.1829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3420   -8.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3420   -9.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6275   -9.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9131   -9.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1986   -9.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4841   -9.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7696   -9.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0552   -9.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407   -9.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262   -9.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9118   -9.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6275   -7.9454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1973   -9.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4828   -9.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7683   -9.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7683   -8.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4828   -7.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1973   -8.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3420   -6.7079    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  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  8 19  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 18 20  1  0
  2  8  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3289508

   2-[(E)-1-hydroxy-11-phenylundec-10-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: 354.49

Molecular Weight (Monoisotopic): 354.2195

AlogP: 5.95

#Rotatable Bonds: 11

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.12

CX Basic pKa: ┄

CX LogP: 6.13

CX LogD: 3.87

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.39

Np Likeness Score: 0.89

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