rac-sodium O-3-methoxy-2-(stearoyloxy)propyl O-hydrogenphosphorothioate

ID: ALA2335051

PubChem CID: 71569056

Max Phase: Preclinical

Molecular Formula: C22H44NaO6PS

Molecular Weight: 468.64

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H45O6PS.Na/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(23)28-21(19-26-2)20-27-29(24,25)30;/h21H,3-20H2,1-2H3,(H2,24,25,30);/q;+1/p-1

Standard InChI Key:  KTWPYUZVWBPKHU-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 31 29  0  0  0  0  0  0  0  0999 V2000
    8.1542  -10.3667    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.7209   -9.5293    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375  -10.2459    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.5498   -9.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667  -10.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2812  -10.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9956  -10.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101  -10.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246  -10.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8535  -10.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9956  -11.4876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8522  -10.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1390  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8535  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5680  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2824  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9969  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7115  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4259  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1404  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8549  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5693  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2838  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9983  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7127  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4272  -11.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1417  -11.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101  -12.7251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8561  -11.4876    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
 12 30  2  0
 29 31  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: 468.64

Molecular Weight (Monoisotopic): 468.2674

AlogP: 6.03

#Rotatable Bonds: 22

Polar Surface Area: 85.22

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.01

CX Basic pKa: ┄

CX LogP: 7.38

CX LogD: 4.02

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.11

Np Likeness Score: 0.69

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