(RS)-O-2-methoxy-3-(octadecyloxy)propyl O,O-dihydrogen phosphorothioate

ID: ALA2335052

PubChem CID: 11648176

Max Phase: Preclinical

Molecular Formula: C22H47O5PS

Molecular Weight: 454.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCCOCC(COP(O)(O)=S)OC

Standard InChI:  InChI=1S/C22H47O5PS/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26-20-22(25-2)21-27-28(23,24)29/h22H,3-21H2,1-2H3,(H2,23,24,29)

Standard InChI Key:  JYAROLONGLXUOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   32.5536  -25.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8486  -25.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1382  -25.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4332  -25.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7229  -25.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0179  -25.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3075  -25.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6025  -25.8939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8921  -25.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1871  -25.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4767  -25.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7717  -25.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0613  -25.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3563  -25.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6459  -25.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9409  -25.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2305  -25.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5255  -25.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3856  -24.7386    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.7984  -25.4485    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   37.2068  -24.7361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2613  -25.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9690  -25.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6768  -25.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3845  -25.4526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0922  -25.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.5076  -25.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6768  -26.6784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3845  -27.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 20 19  2  0
 21 20  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 20  1  0
 20 27  1  0
 24 28  1  0
 22  1  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2335052

   Dihydroxy-(2-methoxy-3-octadecoxypropoxy)-sulfanylidene-lambda5-phosphane

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: 454.65

Molecular Weight (Monoisotopic): 454.2882

AlogP: 6.51

#Rotatable Bonds: 23

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: 2.15

CX Basic pKa: ┄

CX LogP: 7.76

CX LogD: 4.53

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.14

Np Likeness Score: 0.61

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