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

ID: ALA2335047

PubChem CID: 71720690

Max Phase: Preclinical

Molecular Formula: C22H47O5PS

Molecular Weight: 454.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCCOC[C@@H](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)/t22-/m0/s1

Standard InChI Key:  JYAROLONGLXUOT-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

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   30.5811  -18.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8761  -19.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1657  -18.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4607  -19.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.8285  -17.9163    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.2412  -18.6262    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   36.6496  -17.9138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7042  -19.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4119  -18.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1196  -19.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8273  -18.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5350  -19.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.9504  -19.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1196  -19.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8273  -20.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 20 19  2  0
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 24 25  1  0
 25 26  1  0
 26 20  1  0
 20 27  1  0
 24 28  1  1
 22  1  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2335047

   dihydroxy-[(2S)-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