1,1-difluoro-3(S)-hydroxyl-4-oleoyloxylbutane 1,3-cyclic phosphonate

ID: ALA215722

PubChem CID: 44414935

Max Phase: Preclinical

Molecular Formula: C22H41F2O5P

Molecular Weight: 454.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCC(=O)OC[C@@H]1CC(F)(F)P(=O)(O)O1

Standard InChI:  InChI=1S/C22H41F2O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(25)28-19-20-18-22(23,24)30(26,27)29-20/h20H,2-19H2,1H3,(H,26,27)/t20-/m0/s1

Standard InChI Key:  CPQAPUVUTZHEAA-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

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   -3.5296  -20.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3889  -21.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740  -20.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0410  -21.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518  -20.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667  -21.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0373  -20.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7522  -21.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4631  -20.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1780  -21.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8939  -20.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6096  -21.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8899  -19.9663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3257  -20.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0414  -21.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312  -22.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9404  -22.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3547  -21.4717    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.7970  -20.8605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9387  -20.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6514  -22.5988    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5225  -22.8988    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.8639  -22.1174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 22 21  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 25 27  2  0
 24 28  1  0
  1  2  1  0
 24 29  1  0
  2  3  1  0
 25 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA215722

   1,1-difluoro-3(S)-hydroxyl-4-oleoyloxylbutane 1,3-cyclic phosphonate

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: 454.54

Molecular Weight (Monoisotopic): 454.2660

AlogP: 7.36

#Rotatable Bonds: 18

Polar Surface Area: 72.83

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -0.09

CX Basic pKa: ┄

CX LogP: 6.75

CX LogD: 4.44

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.13

Np Likeness Score: 0.35

References

1. Xu Y, Jiang G, Tsukahara R, Fujiwara Y, Tigyi G, Prestwich GD..  (2006)  Phosphonothioate and fluoromethylene phosphonate analogues of cyclic phosphatidic acid: Novel antagonists of lysophosphatidic acid receptors.,  49  (17): [PMID:16913720] [10.1021/jm060351+]

Source

Source(1):

• Scientific Literature