O-2-methoxy-3-(stearoyloxy)propyl phosphorothioate

ID: ALA2017139

PubChem CID: 46223906

Max Phase: Preclinical

Molecular Formula: C22H45O6PS

Molecular Weight: 468.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)S)OC

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

Standard InChI Key:  AYKYANCQUONAPE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.8557  -17.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409  -17.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8634  -18.6685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5824  -14.1212    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.7545  -14.1212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4062  -14.1212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8324  -13.4224    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5824  -17.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1589  -16.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1617  -15.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8764  -14.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
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  1 14  1  0
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 21 22  1  0
 22 23  2  0
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 16 26  1  0
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  1  2  1  0
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  2  3  1  0
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  3  4  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2017139

   (3-Dihydroxyphosphinothioyloxy-2-methoxypropyl) octadecanoate

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: 6.85

#Rotatable Bonds: 22

Polar Surface Area: 82.06

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.94

CX Basic pKa: ┄

CX LogP: 7.24

CX LogD: 5.49

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.08

Np Likeness Score: 0.64

References

1. Gendaszewska-Darmach E, Laska E, Rytczak P, Okruszek A..  (2012)  The chemical synthesis of metabolically stabilized 2-OMe-LPA analogues and preliminary studies of their inhibitory activity toward autotaxin.,  22  (8): [PMID:22460025] [10.1016/j.bmcl.2012.03.008]

2. 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