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rac-(E/Z)-(4-(2-ethylhexylidene)-2-(hydroxymethyl)-5-oxo-tetrahydrofuran-2-yl)methyl 4-(dimethylamino)benzoate

ID: ALA472356

PubChem CID: 25053335

Max Phase: Preclinical

Molecular Formula: C23H33NO5

Molecular Weight: 403.52

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCCCC(/C=C1/CC(CO)(COC(=O)c2ccc(N(C)C)cc2)OC1=O)CC

Standard InChI:  InChI=1S/C23H33NO5/c1-5-7-8-17(6-2)13-19-14-23(15-25,29-22(19)27)16-28-21(26)18-9-11-20(12-10-18)24(3)4/h9-13,17,25H,5-8,14-16H2,1-4H3/b19-13-

Standard InChI Key:  JMKDPOCHTLWPTO-UYRXBGFRSA-N

Molfile:  

     RDKit          2D

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    1.1045  -19.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3595  -18.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6920  -18.0447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246  -18.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441  -18.2747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5895  -19.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4100  -19.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941  -17.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941  -19.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2191  -19.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2191  -17.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345  -17.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595  -17.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250  -16.3853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8949  -20.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154  -20.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2002  -21.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0207  -21.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8698  -16.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6940  -16.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1044  -17.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846  -17.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8618  -17.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294  -17.1163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458  -16.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3381  -17.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7455  -19.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5660  -19.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  2  0
 13 15  2  0
  2  3  1  0
  8 16  1  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  1  0
  5  9  1  0
 18 19  1  0
  4  5  1  0
 14 20  2  0
  5 10  1  0
 20 21  1  0
  5  1  1  0
 21 22  2  0
 10 11  1  0
 22 23  1  0
  1  2  1  0
 23 24  2  0
 24 14  1  0
  9 12  1  0
 22 25  1  0
  3  6  2  0
 25 26  1  0
 12 13  1  0
 25 27  1  0
  8 28  1  0
 13 14  1  0
 28 29  1  0
M  END

Associated Targets(non-human)

Prkca Protein kinase C alpha (292 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 403.52Molecular Weight (Monoisotopic): 403.2359AlogP: 3.73#Rotatable Bonds: 10
Polar Surface Area: 76.07Molecular Species: NEUTRALHBA: 6HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 2.90CX LogP: 4.94CX LogD: 4.94
Aromatic Rings: 1Heavy Atoms: 29QED Weighted: 0.47Np Likeness Score: 0.89

References

1. Duan D, Sigano DM, Kelley JA, Lai CC, Lewin NE, Kedei N, Peach ML, Lee J, Abeyweera TP, Rotenberg SA, Kim H, Kim YH, El Kazzouli S, Chung JU, Young HA, Young MR, Baker A, Colburn NH, Haimovitz-Friedman A, Truman JP, Parrish DA, Deschamps JR, Perry NA, Surawski RJ, Blumberg PM, Marquez VE..  (2008)  Conformationally constrained analogues of diacylglycerol. 29. Cells sort diacylglycerol-lactone chemical zip codes to produce diverse and selective biological activities.,  51  (17): [PMID:18698758] [10.1021/jm8001907]
2. Duan D, Sigano DM, Kelley JA, Lai CC, Lewin NE, Kedei N, Peach ML, Lee J, Abeyweera TP, Rotenberg SA, Kim H, Kim YH, El Kazzouli S, Chung JU, Young HA, Young MR, Baker A, Colburn NH, Haimovitz-Friedman A, Truman JP, Parrish DA, Deschamps JR, Perry NA, Surawski RJ, Blumberg PM, Marquez VE..  (2008)  Conformationally constrained analogues of diacylglycerol. 29. Cells sort diacylglycerol-lactone chemical zip codes to produce diverse and selective biological activities.,  51  (17): [PMID:18698758] [10.1021/jm8001907]

Source