2,5-dimethoxy-3-undecylcyclohexa-2,5-diene-1,4-dione

ID: ALA2296071

Cas Number: 14065-83-9

PubChem CID: 5086864

Max Phase: Preclinical

Molecular Formula: C19H30O4

Molecular Weight: 322.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC1=C(OC)C(=O)C=C(OC)C1=O

Standard InChI:  InChI=1S/C19H30O4/c1-4-5-6-7-8-9-10-11-12-13-15-18(21)17(22-2)14-16(20)19(15)23-3/h14H,4-13H2,1-3H3

Standard InChI Key:  AUSJVHOZNUUITQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
   33.2036  -11.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2036  -11.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9088  -12.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6141  -11.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6141  -11.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9088  -10.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9088   -9.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9088  -13.1452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4947  -10.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3230  -10.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0295  -11.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7323  -10.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4381  -11.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1438  -10.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8496  -11.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5554  -10.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2611  -11.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9669  -10.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6726  -11.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3784  -10.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7881  -11.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3212  -12.3332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3200  -13.1504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  3  8  2  0
  1  9  1  0
  5 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
  9 21  1  0
  4 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296071

   2,5-Dimethoxy-3-undecyl-[1,4]benzoquinone

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: 322.44

Molecular Weight (Monoisotopic): 322.2144

AlogP: 4.49

#Rotatable Bonds: 12

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: 5.05

CX LogD: 5.05

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.39

Np Likeness Score: 1.66

References

1. Muriuki B, Midiwo JO, Mbugua PM, Keriko JM.  (2013)  The antimycobacterial MICs, SARs, and QSARs of some ethnobotanically selected phytocompounds,  22  (11): [10.1007/s00044-013-0485-8]

2. Chen F, Zhang G, Hong Z, Lin Z, Lei M, Huang M, Hu L..  (2014)  Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1).,  24  (10): [PMID:24731276] [10.1016/j.bmcl.2014.03.045]

3. 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