Hexadecanoic acid (S)-2-fluoro-3-phosphonooxy-propyl ester

ID: ALA192452

PubChem CID: 11080129

Max Phase: Preclinical

Molecular Formula: C19H38FO6P

Molecular Weight: 412.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)OC[C@H](F)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)25-16-18(20)17-26-27(22,23)24/h18H,2-17H2,1H3,(H2,22,23,24)/t18-/m0/s1

Standard InChI Key:  PFVWNLWCDVTLPW-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  1  0  0  0  0  0999 V2000
   10.1417   -1.7417    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.7500   -1.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167   -2.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9167   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -1.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8667   -1.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5417   -2.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292   -0.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8042   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292    0.4333    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9417   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -0.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1958   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3333   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2542    0.1083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4  1  2  0
  5  2  1  0
  6  3  2  0
  7 11  1  0
  8  1  1  0
  9  1  1  0
 10  5  1  0
 11 10  1  0
 10 12  1  6
 13  3  1  0
 14 13  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:

   

   ALA192452

   Hexadecanoic acid (S)-2-fluoro-3-phosphonooxy-propyl ester

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: 1.21

CX Basic pKa: ┄

CX LogP: 5.85

CX LogD: 2.30

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.17

Np Likeness Score: 0.36

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