Hexadecanoic acid (S)-3-fluoro-1-hydroxymethyl-3-phosphono-propyl ester

ID: ALA192107

PubChem CID: 44400424

Max Phase: Preclinical

Molecular Formula: C21H42FO6P

Molecular Weight: 440.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)O[C@H](COC)CC(F)P(=O)(O)O

Standard InChI:  InChI=1S/C21H42FO6P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-21(23)28-19(18-27-2)17-20(22)29(24,25)26/h19-20H,3-18H2,1-2H3,(H2,24,25,26)/t19-,20?/m0/s1

Standard InChI Key:  LKADQADNCLDKMS-XJDOXCRVSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  1  0  0  0  0  0999 V2000
    9.2167   -1.6125    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8292   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2167   -2.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9917   -1.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7917   -1.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667    0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1417   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292   -0.4875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0458   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0292    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8208   -0.3000    0.0000 C   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  6  1  0
 10  6  1  1
  7  1  1  0
  8  1  1  0
  9  5  2  0
 10  3  1  0
 11  2  1  0
 12 14  1  0
 13  5  1  0
 14 10  1  0
 15 12  1  0
 16 13  1  0
 17 18  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 16  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 19  1  0
 29 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA192107

   [(3S)-1-fluoro-3-hexadecanoyloxy-4-methoxybutyl]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: 440.53

Molecular Weight (Monoisotopic): 440.2703

AlogP: 5.89

#Rotatable Bonds: 20

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: 1.20

CX Basic pKa: ┄

CX LogP: 5.24

CX LogD: 2.79

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.14

Np Likeness Score: 0.37

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