Methyl 3,3-difluoro-2-(hexadecyloxy)-7-methyl-2,3,4,5-tetrahydro-1,2-oxaphosphepine-6-carboxylate 2-oxide

ID: ALA3401169

PubChem CID: 118728281

Max Phase: Preclinical

Molecular Formula: C24H43F2O5P

Molecular Weight: 480.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCOP1(=O)OC(C)=C(C(=O)OC)CCC1(F)F

Standard InChI:  InChI=1S/C24H43F2O5P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-30-32(28)24(25,26)19-18-22(21(2)31-32)23(27)29-3/h4-20H2,1-3H3

Standard InChI Key:  HNIVQWHVNRILLQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
    1.6852   -0.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    1.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3515    1.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0435   -2.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -1.6217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896    1.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0351    3.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698   -0.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5664   -0.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7550    1.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2517    1.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0977    3.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5943    2.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4403    4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9370    4.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7830    5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2796    5.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1256    6.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6222    6.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4682    7.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6649    7.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3064    5.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622   -0.4610    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -1.6111    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  6  2  0
  1  3  1  0
  3  4  1  0
  7  5  1  0
  4  5  1  0
  6  7  1  0
  8  9  1  0
  9  6  1  0
  3 10  2  0
  3 11  1  0
  2 12  1  0
  9 13  2  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  8 30  1  0
  4 31  1  0
  4 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3401169

   ---

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: 480.57

Molecular Weight (Monoisotopic): 480.2816

AlogP: 8.53

#Rotatable Bonds: 17

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.52

CX LogD: 7.52

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.12

Np Likeness Score: 0.29

References

1. Vasilieva E, Dutta S, Malla RK, Martin BP, Spilling CD, Dupureur CM..  (2015)  Rat hormone sensitive lipase inhibition by cyclipostins and their analogs.,  23  (5): [PMID:25678014] [10.1016/j.bmc.2015.01.028]

Source

Source(1):

• Scientific Literature