3-hydroxyl-4-palmitoyloxylbutane 1,3-cyclic phosphonothioate

ID: ALA211465

PubChem CID: 11849496

Max Phase: Preclinical

Molecular Formula: C20H39O4PS

Molecular Weight: 406.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)OCC1CCP(O)(=S)O1

Standard InChI:  InChI=1S/C20H39O4PS/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(21)23-18-19-16-17-25(22,26)24-19/h19H,2-18H2,1H3,(H,22,26)

Standard InChI Key:  HGTUZBIEGDZLRZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -1.9997  -10.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846   -9.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5695  -10.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1455   -9.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8606  -10.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715   -9.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2866  -10.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0016   -9.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167  -10.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4318   -9.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1468  -10.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8619   -9.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5728  -10.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2879   -9.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0029  -10.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7187   -9.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4370  -10.3140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7160   -9.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1527   -9.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8711  -10.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9630  -11.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7729  -11.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1822  -10.5778    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6293   -9.9678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7673   -9.9902    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.6962  -11.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 13 14  1  0
  3  4  1  0
 14 15  1  0
  7  8  1  0
 15 16  1  0
 16 17  1  0
  8  9  1  0
 16 18  2  0
  4  5  1  0
 17 19  1  0
  9 10  1  0
 19 20  1  0
 20 21  1  0
  2  3  1  0
 10 11  1  0
  5  6  1  0
 11 12  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
  1  2  1  0
 23 25  2  0
 12 13  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA211465

   3-Hydroxyl-4-palmitoyloxylbutane 1,3-cyclic phosphonothioate

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: 406.57

Molecular Weight (Monoisotopic): 406.2307

AlogP: 6.10

#Rotatable Bonds: 16

Polar Surface Area: 55.76

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.92

CX Basic pKa: ┄

CX LogP: 5.98

CX LogD: 3.67

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.19

Np Likeness Score: 0.41

References

1. Xu Y, Jiang G, Tsukahara R, Fujiwara Y, Tigyi G, Prestwich GD..  (2006)  Phosphonothioate and fluoromethylene phosphonate analogues of cyclic phosphatidic acid: Novel antagonists of lysophosphatidic acid receptors.,  49  (17): [PMID:16913720] [10.1021/jm060351+]

Source

Source(1):

• Scientific Literature