Octadecanoic acid (R)-2-methoxy-3-thiophosphonooxy-propyl ester

ID: ALA153043

PubChem CID: 44368508

Max Phase: Preclinical

Molecular Formula: C22H45O6PS

Molecular Weight: 468.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCC(=O)OC[C@H](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)/t21-/m1/s1

Standard InChI Key:  AYKYANCQUONAPE-OAQYLSRUSA-N

Molfile:  

     RDKit          2D

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   10.1667   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875    2.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5250    1.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8167   -0.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5292   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -2.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375   -3.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0500   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  7  1  0
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  7 11  1  0
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 30 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA153043

   [(2R)-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: 6.03

#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: 1.97

CX Basic pKa: ┄

CX LogP: 7.38

CX LogD: 3.99

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.11

Np Likeness Score: 0.78

References

1. Qian L, Xu Y, Hasegawa Y, Aoki J, Mills GB, Prestwich GD..  (2003)  Enantioselective responses to a phosphorothioate analogue of lysophosphatidic acid with LPA3 receptor-selective agonist activity.,  46  (26): [PMID:14667211] [10.1021/jm034207p]

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