Sodium O-2-(hexadecyloxy)-3-methoxypropyl O-hydrogenphosphorothioate

ID: ALA2335049

PubChem CID: 71569053

Max Phase: Preclinical

Molecular Formula: C20H42NaO5PS

Molecular Weight: 426.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCOC(COC)COP([O-])(O)=S.[Na+]

Standard InChI:  InChI=1S/C20H43O5PS.Na/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24-20(18-23-2)19-25-26(21,22)27;/h20H,3-19H2,1-2H3,(H2,21,22,27);/q;+1/p-1

Standard InChI Key:  QZHWXBYUIWJGDD-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 28 26  0  0  0  0  0  0  0  0999 V2000
    7.9532   -2.7240    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.5676   -1.9109    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9804   -2.6208    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.3888   -1.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433   -3.0335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510   -2.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587   -3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5664   -2.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2742   -3.0335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6896   -3.0335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8587   -3.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5664   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2742   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356   -2.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6896   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3973   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1050   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8127   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5204   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2281   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9358   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6435   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3512   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0589   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7667   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4744   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1821   -3.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  3  1  0
  3 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
  5 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  CHG  2   1   1  10  -1
M  END

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: 426.60

Molecular Weight (Monoisotopic): 426.2569

AlogP: 5.73

#Rotatable Bonds: 21

Polar Surface Area: 68.15

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.18

CX Basic pKa: ┄

CX LogP: 6.87

CX LogD: 3.67

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.18

Np Likeness Score: 0.56

References

1. Jiang G, Inoue A, Aoki J, Prestwich GD..  (2013)  Phosphorothioate analogs of sn-2 radyl lysophosphatidic acid (LPA): metabolically stabilized LPA receptor agonists.,  23  (6): [PMID:23395664] [10.1016/j.bmcl.2013.01.002]

Source

Source(1):

• Scientific Literature