3-Hydroxy-2-(15'-phenyl-18'-methylenedioxypentadecanoyl)-cyclohex-2-en-1-one

ID: ALA3289510

PubChem CID: 90681782

Max Phase: Preclinical

Molecular Formula: C18H20O5

Molecular Weight: 316.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCc1ccc2c(c1)OCO2)C1=C(O)CCCC1=O

Standard InChI:  InChI=1S/C18H20O5/c19-13(18-14(20)6-3-7-15(18)21)5-2-1-4-12-8-9-16-17(10-12)23-11-22-16/h8-10,20H,1-7,11H2

Standard InChI Key:  RLKDGAPTORBSIH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   15.7959   -3.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0868   -2.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0868   -1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7959   -1.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5009   -1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5009   -2.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7959   -3.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3819   -3.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3819   -3.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6728   -4.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9637   -3.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6728   -2.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3819   -1.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2563   -4.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5483   -3.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5506   -3.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8434   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8462   -4.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1384   -3.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1391   -3.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3610   -2.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8793   -3.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3599   -4.0994    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
  8 12  2  0
  2  8  1  0
  3 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 20  2  0
 19 18  2  0
 18 15  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3289510

   2-[5-(1,3-Benzodioxol-5-yl)-1-hydroxypentylidene]cyclohexane-1,3-dione

Molecule Features

Natural Product: Yes

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: 316.35

Molecular Weight (Monoisotopic): 316.1311

AlogP: 3.26

#Rotatable Bonds: 6

Polar Surface Area: 72.83

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.87

CX Basic pKa: ┄

CX LogP: 3.37

CX LogD: 0.88

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: 0.62

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