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

ID: ALA382784

PubChem CID: 11718329

Max Phase: Preclinical

Molecular Formula: C24H34O5

Molecular Weight: 402.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CC(C/C=C1/CC(CO)(COC(=O)c2ccccc2)OC1=O)CC(C)C

Standard InChI:  InChI=1S/C24H34O5/c1-17(2)12-19(13-18(3)4)10-11-21-14-24(15-25,29-23(21)27)16-28-22(26)20-8-6-5-7-9-20/h5-9,11,17-19,25H,10,12-16H2,1-4H3/b21-11-

Standard InChI Key:  BKNVHJDEURXREP-NHDPSOOVSA-N

Molfile:  

     RDKit          2D

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   16.1511  -17.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9941  -18.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1735  -18.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8371  -19.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6893  -17.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4875  -16.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3081  -16.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0034  -16.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5416  -16.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7984  -15.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1291  -15.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4641  -15.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5834  -15.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8750  -15.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7458  -16.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0356  -15.7677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0897  -14.3951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5073  -13.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7101  -14.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7220  -13.0143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1317  -13.4366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3351  -13.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1197  -14.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7071  -15.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5014  -14.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  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
 22 24  2  0
  1  2  1  0
 23 25  2  0
  5  7  1  0
 25 26  1  0
  2  4  1  0
 26 27  2  0
  3  8  1  0
 27 28  1  0
 13 14  1  0
 28 29  2  0
 29 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA382784

   5-benzoyloxymethyl-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: 402.53

Molecular Weight (Monoisotopic): 402.2406

AlogP: 4.55

#Rotatable Bonds: 10

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: 5.85

CX LogD: 5.85

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.46

Np Likeness Score: 1.03

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