Hexadecanoic acid (S)-2-fluoro-1-phosphonooxymethyl-ethyl ester

ID: ALA190771

PubChem CID: 11026029

Max Phase: Preclinical

Molecular Formula: C19H38FO6P

Molecular Weight: 412.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)O[C@@H](CF)COP(=O)(O)O

Standard InChI:  InChI=1S/C19H38FO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)26-18(16-20)17-25-27(22,23)24/h18H,2-17H2,1H3,(H2,22,23,24)/t18-/m0/s1

Standard InChI Key:  JTRDAOCJEIRXNJ-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  1  0  0  0  0  0999 V2000
    0.9875   -3.4375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2750   -3.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -2.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958   -1.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -3.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1583   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -3.0250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3750   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458   -2.6042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  1  2  0
 10  5  1  6
  6  3  1  0
  7  2  2  0
  8  1  1  0
  9  1  1  0
 10  6  1  0
 11 13  1  0
 12  2  1  0
 13 10  1  0
 14 12  1  0
 15 16  1  0
 16 23  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 14  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 17  1  0
 27 15  1  0
 10 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA190771

   [(2R)-1-fluoro-3-phosphonooxypropan-2-yl] hexadecanoate

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: 412.48

Molecular Weight (Monoisotopic): 412.2390

AlogP: 5.46

#Rotatable Bonds: 19

Polar Surface Area: 93.06

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.30

CX Basic pKa: ┄

CX LogP: 5.85

CX LogD: 2.39

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.17

Np Likeness Score: 0.59

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