Hexadecanoic acid (R)-2,2-difluoro-1-phosphonooxymethyl-ethyl ester

ID: ALA195383

PubChem CID: 11122865

Max Phase: Preclinical

Molecular Formula: C19H37F2O6P

Molecular Weight: 430.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H37F2O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(22)27-17(19(20)21)16-26-28(23,24)25/h17,19H,2-16H2,1H3,(H2,23,24,25)/t17-/m1/s1

Standard InChI Key:  FNESAIQQDLSXRX-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  1  0  0  0  0  0999 V2000
   15.1292    2.1083    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.7125    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9917    0.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4167    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1292   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2792    0.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4167    1.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5500    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2750    1.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7125    2.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8417    2.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7167   -0.9792    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9542   -0.2542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5750    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8542    0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7167    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4292    0.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1417    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2917    1.1625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  2  3  1  6
  4  7  1  0
  5  2  1  0
  6  3  1  0
  7  1  1  0
  8  1  2  0
  9  6  2  0
 10  1  1  0
 11  1  1  0
 12  5  1  0
 13  5  1  0
 14  6  1  0
 15 14  1  0
 16 17  1  0
 17 23  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 15  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 18  1  0
 28 16  1  0
  2 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA195383

   Hexadecanoic acid (R)-2,2-difluoro-1-phosphonooxymethyl-ethyl 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: 430.47

Molecular Weight (Monoisotopic): 430.2296

AlogP: 5.75

#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: 6.11

CX LogD: 2.57

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.15

Np Likeness Score: 0.45

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