Hexadecanoic acid (S)-4-fluoro-2-hydroxy-4-phosphono-butyl ester

ID: ALA192073

PubChem CID: 12109920

Max Phase: Preclinical

Molecular Formula: C20H40FO6P

Molecular Weight: 426.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H40FO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(23)27-17-18(22)16-19(21)28(24,25)26/h18-19,22H,2-17H2,1H3,(H2,24,25,26)/t18-,19?/m0/s1

Standard InChI Key:  XNYDYIXHIQHKEW-OYKVQYDMSA-N

Molfile:  

     RDKit          2D

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    6.2667   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -1.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0292   -0.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -1.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625   -1.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -0.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -0.3167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0167   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -0.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8792   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250   -0.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
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  8  5  2  0
  9 12  1  0
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 12 11  1  0
 11 13  1  1
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 18 19  1  0
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 20 21  1  0
 21 22  1  0
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 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 18  1  0
 28 16  1  0
 11 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA192073

   [(3S)-1-fluoro-4-hexadecanoyloxy-3-hydroxybutyl]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: 426.51

Molecular Weight (Monoisotopic): 426.2547

AlogP: 5.24

#Rotatable Bonds: 19

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: 4.67

CX LogD: 2.21

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.15

Np Likeness Score: 0.35

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