((Z)-2-(Hydroxymethyl)-4-(3-methylbutylidene)-5-oxotetrahydrofuran-2-yl)methyl-(9Z,12Z)-octadeca-9,12-dienoate

ID: ALA3393654

PubChem CID: 118725578

Max Phase: Preclinical

Molecular Formula: C29H48O5

Molecular Weight: 476.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC/C=C/C/C=C/CCCCCCCC(=O)OCC1(CO)C/C(=C/CC(C)C)C(=O)O1

Standard InChI:  InChI=1S/C29H48O5/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-27(31)33-24-29(23-30)22-26(28(32)34-29)21-20-25(2)3/h8-9,11-12,21,25,30H,4-7,10,13-20,22-24H2,1-3H3/b9-8+,12-11+,26-21-

Standard InChI Key:  JFAIQUNDRVEIFN-UIDAQTEXSA-N

Molfile:  

     RDKit          2D

 34 34  0  0  0  0  0  0  0  0999 V2000
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   -0.4187    5.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070    6.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2219    7.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5167   14.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6316   15.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3199   16.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7500   -1.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553   -2.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375    0.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7555   -0.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1819    0.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0759   -0.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4286    1.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4448   -0.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995    1.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
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 15 16  1  0
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  1 19  2  0
  1 20  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 21 25  1  0
 25 26  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 24 27  2  0
 32 33  1  0
 22 32  1  0
 22 34  1  0
 34 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3393654

   ---

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: 476.70

Molecular Weight (Monoisotopic): 476.3502

AlogP: 6.99

#Rotatable Bonds: 19

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: 8.09

CX LogD: 8.09

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.09

Np Likeness Score: 1.54

References

1. Ann J, Yoon S, Baek J, Kim DH, Lewin NE, Hill CS, Blumberg PM, Lee J..  (2015)  Design and synthesis of protein kinase C epsilon selective diacylglycerol lactones (DAG-lactones).,  90  [PMID:25437619] [10.1016/j.ejmech.2014.11.025]

Source

Source(1):

• Scientific Literature