2,2-Dimethyl-propionic acid 2-hydroxymethyl-4-(3-isobutyl-5-methyl-hexylidene)-5-oxo-tetrahydro-furan-2-ylmethyl ester

ID: ALA96766

PubChem CID: 5471818

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/CC(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-

Standard InChI Key:  XKEOGEXDEKIDNA-NVMNQCDNSA-N

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    3.3542   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -0.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2750   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -0.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -1.0500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    0.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4125   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -1.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -1.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -4.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -2.0417    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  9  1  0
  6  2  2  0
  7  2  1  0
  8  5  1  0
  9 12  1  0
 10  1  2  0
 11  5  2  0
 12  4  1  0
  6 13  1  0
 14 13  1  0
 15 14  1  0
 16 14  1  0
 17  4  1  0
 18 17  1  0
 19  8  1  0
 20  8  1  0
 21  8  1  0
 22 16  1  0
 23 15  1  0
 24 22  1  0
 25 22  1  0
 26 23  1  0
 27 23  1  0
  7  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA96766

   (Z)-(2-(hydroxymethyl)-4-(3-isobutyl-5-methylhexylidene)-5-oxo-tetrahydrofuran-2-yl)methyl 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. Choi Y, Kang JH, Lewin NE, Blumberg PM, Lee J, Marquez VE..  (2003)  Conformationally constrained analogues of diacylglycerol. 19. Synthesis and protein kinase C binding affinity of diacylglycerol lactones bearing an N-hydroxylamide side chain.,  46  (13): [PMID:12801241] [10.1021/jm030082c]

2. 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]

3. Tamamura H, Sigano DM, Lewin NE, Peach ML, Nicklaus MC, Blumberg PM, Marquez VE..  (2004)  Conformationally constrained analogues of diacylglycerol (DAG). 23. Hydrophobic ligand-protein interactions versus ligand-lipid interactions of DAG-lactones with protein kinase C (PK-C).,  47  (20): [PMID:15369389] [10.1021/jm049723+]

4. Kang JH, Kim SY, Lee J, Marquez VE, Lewin NE, Pearce LV, Blumberg PM..  (2004)  Macrocyclic diacylglycerol-bis-lactones as conformationally constrained analogues of diacylglycerol-lactones. Interactions with protein kinase C.,  47  (16): [PMID:15267238] [10.1021/jm0497747]

5. Kang JH, Peach ML, Pu Y, Lewin NE, Nicklaus MC, Blumberg PM, Marquez VE..  (2005)  Conformationally constrained analogues of diacylglycerol (DAG). 25. Exploration of the sn-1 and sn-2 carbonyl functionality reveals the essential role of the sn-1 carbonyl at the lipid interface in the binding of DAG-lactones to protein kinase C.,  48  (18): [PMID:16134942] [10.1021/jm050352m]

6. 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]

7. Choi Y, Pu Y, Peach ML, Kang JH, Lewin NE, Sigano DM, Garfield SH, Blumberg PM, Marquez VE..  (2007)  Conformationally constrained analogues of diacylglycerol (DAG). 28. DAG-dioxolanones reveal a new additional interaction site in the C1b domain of PKC delta.,  50  (15): [PMID:17591763] [10.1021/jm0702579]

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays