(R,Z)-2-(2-(hydroxymethyl)-4-(3-isobutyl-5-methylhexylidene)-5-oxo-tetrahydrofuran-2-yl)ethyl pivalate

ID: ALA203524

PubChem CID: 44408572

Max Phase: Preclinical

Molecular Formula: C22H38O5

Molecular Weight: 382.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CC(C/C=C1/C[C@@](CO)(COC(=O)C(C)(C)C)OC1=O)CC(C)C

Standard InChI:  InChI=1S/C22H38O5/c1-15(2)10-17(11-16(3)4)8-9-18-12-22(13-23,27-19(18)24)14-26-20(25)21(5,6)7/h9,15-17,23H,8,10-14H2,1-7H3/b18-9-/t22-/m1/s1

Standard InChI Key:  XKEOGEXDEKIDNA-JVGWPHRLSA-N

Molfile:  

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    0.9859   -3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3166   -3.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484   -3.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7709   -3.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7769   -3.6010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2133   -5.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -4.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180   -5.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386   -5.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816   -6.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -6.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246   -7.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4956   -4.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909   -4.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7228   -2.2284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3052   -1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0905   -0.8524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1024   -1.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8917   -2.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -1.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  1  0
  5  7  1  1
 14 15  1  0
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  3  4  1  0
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  2 10  2  0
  7 21  1  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
  1  2  1  0
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  3  6  2  0
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 12 13  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA203524

   (R,Z)-2-(2-(hydroxymethyl)-4-(3-isobutyl-5-methylhexylidene)-5-oxo-tetrahydrofuran-2-yl)ethyl pivalate

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: 382.54

Molecular Weight (Monoisotopic): 382.2719

AlogP: 4.28

#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: 5.59

CX LogD: 5.59

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: 1.16

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