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

ID: ALA380661

PubChem CID: 11682813

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-SRZZPIQSSA-N

Molfile:  

     RDKit          2D

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    1.2243  -24.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4037  -24.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804  -23.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7178  -22.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5164  -19.9848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9027  -18.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8907  -17.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803  -18.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768  -18.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922  -19.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049  -19.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105  -19.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673  -24.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 11  1  0
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 17 20  1  0
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  2  3  1  0
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  5  6  1  0
 21 23  2  0
  1  2  1  0
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  3  7  1  0
 24 25  1  0
  2  4  1  0
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 12 13  1  0
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 13 14  1  0
 27 28  2  0
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 14 15  1  0
  5 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA380661

   5-benzoyloxymethyl-5-hydroxymethyl-3-[(E)-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