2-hydroxy-5-methoxy-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl)-1,4-benzoquinone

ID: ALA3416177

PubChem CID: 118733913

Max Phase: Preclinical

Molecular Formula: C22H30O4

Molecular Weight: 358.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=CC(=O)C(O)=C(C/C=C(\C)CC/C=C(\C)CCC=C(C)C)C1=O

Standard InChI:  InChI=1S/C22H30O4/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-18-21(24)19(23)14-20(26-5)22(18)25/h8,10,12,14,24H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+

Standard InChI Key:  AUDYECRPXIOJSY-JTCWOHKRSA-N

Molfile:  

     RDKit          2D

 26 26  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
   -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
   -7.5628   14.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4845   14.8495    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
   -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
    2.3383    1.3500    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  2  0
  1  6  1  0
  4  7  2  0
  1  8  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  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
 11 23  1  0
  3  9  1  0
 24 25  1  0
  5 24  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3416177

   ---

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: 358.48

Molecular Weight (Monoisotopic): 358.2144

AlogP: 5.29

#Rotatable Bonds: 9

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.54

CX Basic pKa: ┄

CX LogP: 5.03

CX LogD: 3.17

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: 2.43

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]

2. Jiso A, Kittiwisut S, Chantakul R, Yuenyongsawad S, Putchakarn S, Schäberle TF, Temkitthaworn P, Ingkaninan K, Chaithirayanon K, Plubrukarn A..  (2020)  Quintaquinone, a Merosesquiterpene from the Yellow Sponge Verongula cf. rigida Esper.,  83  (2): [PMID:32040314] [10.1021/acs.jnatprod.9b00886]

Source

Source(1):

• Scientific Literature