(E)-Octadec-9-enoic acid (S)-4-fluoro-2-hydroxy-4-phosphono-butyl ester

ID: ALA191946

PubChem CID: 44400388

Max Phase: Preclinical

Molecular Formula: C22H42FO6P

Molecular Weight: 452.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C/CCCCCCCC(=O)OC[C@@H](O)CC(F)P(=O)(O)O

Standard InChI:  InChI=1S/C22H42FO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(25)29-19-20(24)18-21(23)30(26,27)28/h9-10,20-21,24H,2-8,11-19H2,1H3,(H2,26,27,28)/b10-9+/t20-,21?/m0/s1

Standard InChI Key:  YRZFDGAGYVFBGZ-WUFOMUAUSA-N

Molfile:  

     RDKit          2D

 31 30  0  0  1  0  0  0  0  0999 V2000
    7.5917   -1.1792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.0167   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -1.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0625   -0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -1.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -0.9125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0167   -0.3875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -0.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -0.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5958   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0458   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4708   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -0.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  9  1  0
  6  1  1  0
  7  1  1  0
  8  5  2  0
  9 14  1  0
 10 18  1  0
 11 10  2  0
 12  2  1  0
 13  3  1  0
 14 13  1  0
 13 15  1  1
 16  5  1  0
 17 11  1  0
 18 20  1  0
 19 16  1  0
 20 29  1  0
 21 17  1  0
 22 23  1  0
 23 26  1  0
 24 25  1  0
 25 19  1  0
 26 27  1  0
 27 28  1  0
 28 21  1  0
 29 24  1  0
 30 22  1  0
 13 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA191946

   [(3S)-1-fluoro-3-hydroxy-4-[(E)-octadec-9-enoyl]oxybutyl]phosphonic acid

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: 452.54

Molecular Weight (Monoisotopic): 452.2703

AlogP: 5.79

#Rotatable Bonds: 20

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.20

CX Basic pKa: ┄

CX LogP: 5.21

CX LogD: 2.75

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.09

Np Likeness Score: 0.68

References

1. Xu Y, Aoki J, Shimizu K, Umezu-Goto M, Hama K, Takanezawa Y, Yu S, Mills GB, Arai H, Qian L, Prestwich GD..  (2005)  Structure-activity relationships of fluorinated lysophosphatidic acid analogues.,  48  (9): [PMID:15857137] [10.1021/jm049186t]

Source

Source(1):

• Scientific Literature