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

ID: ALA206332

PubChem CID: 11502757

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-XKZIYDEJSA-N

Molfile:  

     RDKit          2D

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   14.2297  -11.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7138  -11.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5344  -11.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3774  -12.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5568  -12.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2204  -13.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0727  -11.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8709  -10.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6914  -10.8144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3867  -10.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4091  -11.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1000  -10.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9250  -10.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1818   -9.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5125   -9.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8474   -9.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9667   -9.4496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2583   -9.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1292  -10.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4190   -9.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4731   -8.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8906   -7.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0934   -7.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5109   -7.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7137   -7.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1312   -6.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1053   -6.9351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3340   -7.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7515   -6.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9543   -6.8282    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:

   

   ALA206332

   5-hydroxymethyl-3-[(Z)-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