(+/-)-3-O-[4-(4,5-dihydro-5-oxo-1,2,4-4H-oxadiazol-3-yl)phenyl]-2-O-tetradecylglycerol

ID: ALA219946

PubChem CID: 135540876

Max Phase: Preclinical

Molecular Formula: C25H40N2O5

Molecular Weight: 448.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCOC(CO)COc1ccc(-c2noc(=O)[nH]2)cc1

Standard InChI:  InChI=1S/C25H40N2O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-18-30-23(19-28)20-31-22-16-14-21(15-17-22)24-26-25(29)32-27-24/h14-17,23,28H,2-13,18-20H2,1H3,(H,26,27,29)

Standard InChI Key:  PTHGHMSPAXULKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    7.6258  -26.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3419  -27.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0605  -26.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0643  -25.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3450  -25.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292  -25.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7735  -27.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8563  -27.9997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6671  -28.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0793  -27.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5266  -26.8434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9037  -27.3772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9037  -25.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6188  -25.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296  -25.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0446  -25.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596  -25.8817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9193  -25.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1934  -25.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4822  -25.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4934  -24.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7823  -24.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915  -25.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4782  -25.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341  -25.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474  -25.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6597  -25.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3730  -25.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836  -25.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7974  -25.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092  -25.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2230  -25.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  3  4  2  0
 16 17  1  0
  4  5  1  0
 18 19  1  0
  2  3  1  0
 19 20  1  0
 20 17  1  0
  7  8  2  0
 20 21  1  0
  9 10  1  0
 21 22  1  0
 18  6  1  0
 10 11  1  0
 13 23  1  0
 11  7  1  0
 23 24  1  0
  5  6  2  0
 24 25  1  0
 10 12  2  0
 25 26  1  0
  6  1  1  0
 26 27  1  0
  1  2  2  0
 27 28  1  0
 13 14  1  0
 28 29  1  0
  3  7  1  0
 29 30  1  0
 14 15  1  0
 30 31  1  0
  8  9  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA219946

   ---

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: 448.60

Molecular Weight (Monoisotopic): 448.2937

AlogP: 5.49

#Rotatable Bonds: 19

Polar Surface Area: 97.58

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.94

CX Basic pKa: ┄

CX LogP: 6.60

CX LogD: 5.75

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.20

References

1. Touaibia M, Djimdé A, Cao F, Boilard E, Bezzine S, Lambeau G, Redeuilh C, Lamouri A, Massicot F, Chau F, Dong CZ, Heymans F..  (2007)  Inhibition of secreted phospholipase A2. 4-glycerol derivatives of 4,5-dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one with broad activities.,  50  (7): [PMID:17335183] [10.1021/jm060082n]

Source

Source(1):

• Scientific Literature