Methyl (6E,8Z,11Z,14Z,17Z)-5-oxo-6,8,11,14-eicosapentaenoate

ID: ALA4130040

PubChem CID: 145962053

Max Phase: Preclinical

Molecular Formula: C21H30O3

Molecular Weight: 330.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC/C=C\C/C=C\C/C=C\C/C=C\C=C\C(=O)CCCC(=O)OC

Standard InChI:  InChI=1S/C21H30O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17-20(22)18-16-19-21(23)24-2/h4-5,7-8,10-11,13-15,17H,3,6,9,12,16,18-19H2,1-2H3/b5-4-,8-7-,11-10-,14-13-,17-15+

Standard InChI Key:  GMLNYELUXRVLGZ-OSDQZAHSSA-N

Molfile:  

     RDKit          2D

 24 23  0  0  0  0  0  0  0  0999 V2000
    2.9404  -20.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2482  -19.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2782  -19.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0004  -18.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6626  -19.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0305  -17.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527  -17.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449  -17.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672  -17.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3548  -20.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248  -21.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8594  -17.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5816  -17.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8294  -18.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2738  -17.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961  -17.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6883  -18.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4105  -17.6396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6583  -18.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026  -21.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726  -22.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648  -22.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2347  -23.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1028  -18.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  1  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  5 10  2  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 11 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 18 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4130040

   ---

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: 330.47

Molecular Weight (Monoisotopic): 330.2195

AlogP: 5.26

#Rotatable Bonds: 13

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.55

CX LogD: 5.55

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.20

Np Likeness Score: 1.23

References

1. Stepniewski TM, Torrens-Fontanals M, Rodríguez-Espigares I, Giorgino T, Primdahl KG, Vik A, Stenstrøm Y, Selent J, Hansen TV..  (2018)  Synthesis, molecular modelling studies and biological evaluation of new oxoeicosanoid receptor 1 agonists.,  26  (12): [PMID:29866479] [10.1016/j.bmc.2018.05.036]

Source

Source(1):

• Scientific Literature