5-[(E)-3-(tert-butoxy)-3-oxo-1-propenyl]-5-hydroxymethyl-3-[(Z)-3-isobutyl-5-methylhexylidene]tetrahydro-2-furanone

ID: ALA204134

PubChem CID: 11494919

Max Phase: Preclinical

Molecular Formula: C23H38O5

Molecular Weight: 394.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CC(C/C=C1/CC(/C=C/C(=O)OC(C)(C)C)(CO)OC1=O)CC(C)C

Standard InChI:  InChI=1S/C23H38O5/c1-16(2)12-18(13-17(3)4)8-9-19-14-23(15-24,28-21(19)26)11-10-20(25)27-22(5,6)7/h9-11,16-18,24H,8,12-15H2,1-7H3/b11-10+,19-9-

Standard InChI Key:  AKVCUOZKJVRCQK-PQONSAHMSA-N

Molfile:  

     RDKit          2D

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   11.8291    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0859    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4166    2.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7516    1.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8709    2.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1625    2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0333    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3231    1.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3133    0.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1339    0.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6180   -0.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4386   -0.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2816   -1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4610   -1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1246   -1.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9768   -0.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7750    0.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5956    0.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2909    1.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3653    2.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7828    2.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9949    3.5203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9829    2.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7913    3.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5833    3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0087    2.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5771    4.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
  5  7  1  0
 14 15  1  0
  2  3  1  0
 15 16  1  0
  5  8  1  0
 15 17  1  0
  3  4  1  0
 13 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 18 20  1  0
  2 10  2  0
  7 21  2  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
  1  2  1  0
 22 23  1  0
 22 24  2  0
 11 12  1  0
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  3  6  2  0
 25 26  1  0
 12 13  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA204134

   5-[(E)-3-(tert-butoxy)-3-oxo-1-propenyl]-5-hydroxymethyl-3-[(Z)-3-isobutyl-5-methylhexylidene]tetrahydro-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: 394.55

Molecular Weight (Monoisotopic): 394.2719

AlogP: 4.59

#Rotatable Bonds: 9

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.63

CX LogD: 5.63

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 1.23

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