3-Hydroxy-2-(3'-phenyl-6'-methylenedioxypropanoyl)cyclohex-2-en-1-one

ID: ALA3289509

PubChem CID: 90681781

Max Phase: Preclinical

Molecular Formula: C16H16O5

Molecular Weight: 288.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCCC(O)=C1C(=O)CCc1ccc2c(c1)OCO2

Standard InChI:  InChI=1S/C16H16O5/c17-11-2-1-3-12(18)16(11)13(19)6-4-10-5-7-14-15(8-10)21-9-20-14/h5,7-8,17H,1-4,6,9H2

Standard InChI Key:  AKVWKQWXOKLWDY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.8605   -2.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1514   -2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1514   -1.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8605   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5654   -1.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5654   -2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8605   -3.6743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464   -2.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464   -3.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7373   -4.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283   -3.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7373   -2.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464   -1.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0304   -2.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3221   -2.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3249   -4.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6161   -3.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6116   -2.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8281   -2.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3483   -3.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354   -3.9381    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  2  0
 14 15  1  0
 15 18  2  0
 17 16  2  0
 16 11  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3289509

   2-[3-(1,3-Benzodioxol-5-yl)-1-hydroxypropylidene]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: 288.30

Molecular Weight (Monoisotopic): 288.0998

AlogP: 2.48

#Rotatable Bonds: 4

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: 4.48

CX Basic pKa: ┄

CX LogP: 2.48

CX LogD: -0.35

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.86

Np Likeness Score: 0.68

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