rac-sodium O-2-(heptadecyloxy)-3-methoxypropyl O-hydrogenphosphorothioate

ID: ALA2335050

PubChem CID: 71718248

Max Phase: Preclinical

Molecular Formula: C21H44NaO5PS

Molecular Weight: 440.63

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H45O5PS.Na/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-25-21(19-24-2)20-26-27(22,23)28;/h21H,3-20H2,1-2H3,(H2,22,23,28);/q;+1/p-1

Standard InChI Key:  JZDLPGVYJPWQNT-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 29 27  0  0  0  0  0  0  0  0999 V2000
    7.7792   -6.4667    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.5917   -5.4917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0084   -6.2084    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.4207   -5.4892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -6.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1520   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664   -6.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5810   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955   -6.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7244   -6.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664   -7.4501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5810   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2955   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230   -6.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0099   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7244   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4389   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1533   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8678   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5823   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2967   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0112   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7257   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4401   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1547   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8692   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5836   -7.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2981   -7.4501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0126   -7.8626    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
 28 29  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: 440.63

Molecular Weight (Monoisotopic): 440.2725

AlogP: 6.12

#Rotatable Bonds: 22

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: 7.32

CX LogD: 4.11

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.16

Np Likeness Score: 0.54

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