5-hydroxymethyl-3-[(E)-3-isobutyl-5-methylhexylidene]-5-octanoyloxymethyltetrahydro-2-furanone

ID: ALA383708

PubChem CID: 11510117

Max Phase: Preclinical

Molecular Formula: C25H44O5

Molecular Weight: 424.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC(=O)OCC1(CO)C/C(=C\CC(CC(C)C)CC(C)C)C(=O)O1

Standard InChI:  InChI=1S/C25H44O5/c1-6-7-8-9-10-11-23(27)29-18-25(17-26)16-22(24(28)30-25)13-12-21(14-19(2)3)15-20(4)5/h13,19-21,26H,6-12,14-18H2,1-5H3/b22-13+

Standard InChI Key:  UJBGCVAQDSYQPK-LPYMAVHISA-N

Molfile:  

     RDKit          2D

 30 30  0  0  0  0  0  0  0  0999 V2000
    1.3477  -16.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318  -16.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524  -16.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954  -17.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748  -17.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3384  -18.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1907  -17.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9888  -16.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094  -16.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5047  -15.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841  -15.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750  -14.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000  -14.8959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4568  -14.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875  -13.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1224  -14.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417  -13.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4667  -13.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958  -14.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060  -14.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2519  -12.7243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344  -12.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6316  -12.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141  -11.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113  -11.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5938  -11.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6197  -11.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3910  -11.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735  -11.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7627  -11.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 16 12  1  0
 14 17  2  0
  8  9  1  0
 16 18  1  0
  4  5  1  0
 16 19  1  0
  8 10  1  0
 19 20  1  0
 13 11  2  0
  2  3  1  0
 18 21  1  0
  1 11  1  0
 21 22  1  0
 12 13  1  0
 22 23  1  0
  5  6  1  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
  5  7  1  0
 25 26  1  0
  2  4  1  0
 22 27  2  0
  3  8  1  0
 26 28  1  0
 13 14  1  0
 28 29  1  0
 14 15  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA383708

   5-hydroxymethyl-3-[(E)-3-isobutyl-5-methylhexylidene]-5-octanoyloxymethyltetrahydro-2-furanone

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: 424.62

Molecular Weight (Monoisotopic): 424.3189

AlogP: 5.59

#Rotatable Bonds: 15

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.72

CX LogD: 6.72

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.21

Np Likeness Score: 1.24

References

1. Lee J, Kang JH, Han KC, Kim Y, Kim SY, Youn HS, Mook-Jung I, Kim H, Lo Han JH, Ha HJ, Kim YH, Marquez VE, Lewin NE, Pearce LV, Lundberg DJ, Blumberg PM..  (2006)  Branched diacylglycerol-lactones as potent protein kinase C ligands and alpha-secretase activators.,  49  (6): [PMID:16539391] [10.1021/jm0509391]

Source

Source(1):

• Scientific Literature