(E)-3-(3,7-dimethylocta-2,6-dienyl)-4,5-dimethoxy-1,2-benzoquinone

ID: ALA3416364

PubChem CID: 118734025

Max Phase: Preclinical

Molecular Formula: C18H24O4

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=CC(=O)C(=O)C(C/C=C(\C)CCC=C(C)C)=C1OC

Standard InChI:  InChI=1S/C18H24O4/c1-12(2)7-6-8-13(3)9-10-14-17(20)15(19)11-16(21-4)18(14)22-5/h7,9,11H,6,8,10H2,1-5H3/b13-9+

Standard InChI Key:  HTJGODRIWLDNFU-UKTHLTGXSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078    5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    8.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149    9.7490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9550   10.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8767   10.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688    5.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  1  6  1  0
  2  7  2  0
  1  8  2  0
  9 10  1  0
  5  9  1  0
 11 12  1  0
  4 11  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 15 22  1  0
  3 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3416364

   ---

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: 304.39

Molecular Weight (Monoisotopic): 304.1675

AlogP: 3.65

#Rotatable Bonds: 7

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.41

Np Likeness Score: 2.38

References

1. Filosa R, Peduto A, Schaible AM, Krauth V, Weinigel C, Barz D, Petronzi C, Bruno F, Roviezzo F, Spaziano G, D'Agostino B, De Rosa M, Werz O..  (2015)  Novel series of benzoquinones with high potency against 5-lipoxygenase in human polymorphonuclear leukocytes.,  94  [PMID:25765759] [10.1016/j.ejmech.2015.02.042]

Source

Source(1):

• Scientific Literature