2,5-dimethoxy-3-hexadecyl-1,4-benzoquinone

ID: ALA3416351

PubChem CID: 117872651

Max Phase: Preclinical

Molecular Formula: C24H40O4

Molecular Weight: 392.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCC1=C(OC)C(=O)C=C(OC)C1=O

Standard InChI:  InChI=1S/C24H40O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-23(26)22(27-2)19-21(25)24(20)28-3/h19H,4-18H2,1-3H3

Standard InChI Key:  AKNPAZKGOWWPLZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
   -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
   -5.2157   10.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2188   11.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5196   12.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5227   14.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8235   14.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8266   16.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1274   17.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1305   18.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1706   19.3450    0.0000 C   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
    2.5972    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
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  1  6  1  0
  4  7  2  0
  1  8  2  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  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  3  9  1  0
 25 26  1  0
  5 25  1  0
 27 28  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3416351

   3-Hexadecyl-2,5-dimethoxycyclohexa-2,5-diene-1,4-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: 392.58

Molecular Weight (Monoisotopic): 392.2927

AlogP: 6.44

#Rotatable Bonds: 17

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.28

CX LogD: 7.28

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.21

Np Likeness Score: 1.36

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