3-Isopropyl-4-methyl-pentanoic acid 2-hydroxymethyl-4-(3-isobutyl-5-methyl-hexylidene)-5-oxo-tetrahydro-furan-2-ylmethyl ester

ID: ALA138171

PubChem CID: 11026526

Max Phase: Preclinical

Molecular Formula: C26H46O5

Molecular Weight: 438.65

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H46O5/c1-17(2)11-21(12-18(3)4)9-10-22-14-26(15-27,31-25(22)29)16-30-24(28)13-23(19(5)6)20(7)8/h10,17-21,23,27H,9,11-16H2,1-8H3/b22-10+

Standard InChI Key:  PKVDZHIWRHABMS-LSHDLFTRSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
    4.5167  -10.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625  -11.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500  -10.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875  -10.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7500  -12.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375  -11.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -7.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -9.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -8.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042  -10.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -9.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -9.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -9.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125  -12.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -6.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -7.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917  -13.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542  -14.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167  -13.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000  -11.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042  -10.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542  -12.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375  -14.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -6.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -6.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -8.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750  -12.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667  -11.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042  -15.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542  -13.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  2  2  0
  6  2  1  0
  7  9  1  0
  8 12  1  0
  9  8  1  0
 10  1  2  0
 11  8  2  0
 12 13  1  0
 13  4  1  0
 14  5  1  0
 15  7  1  0
 16  7  1  0
 17 14  1  0
 18 17  1  0
 19 17  1  0
 20  4  1  0
 21 20  1  0
 22 19  1  0
 23 18  1  0
 24 15  1  0
 25 15  1  0
 26 16  1  0
 27 16  1  0
 28 22  1  0
 29 22  1  0
 30 23  1  0
 31 23  1  0
  4  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA138171

   5-hydroxymethyl-3-[(E)-3-isobutyl-5-methylhexylidene]-5-(3-isopropyl-4-methyl-pentanoyloxymethyl)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: 438.65

Molecular Weight (Monoisotopic): 438.3345

AlogP: 5.55

#Rotatable Bonds: 13

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: 6.69

CX LogD: 6.69

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: 1.39

References

1. Lee J, Han KC, Kang JH, Pearce LL, Lewin NE, Yan S, Benzaria S, Nicklaus MC, Blumberg PM, Marquez VE..  (2001)  Conformationally constrained analogues of diacylglycerol. 18. The incorporation of a hydroxamate moiety into diacylglycerol-lactones reduces lipophilicity and helps discriminate between sn-1 and sn-2 binding modes to protein kinase C (PK-C). Implications for isozyme specificity.,  44  (25): [PMID:11728178] [10.1021/jm0103965]

2. 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