octadecyl [2-(trimethylphosphaniumyl)ethyl] phosphate

ID: ALA229517

Cas Number: 156825-89-7

PubChem CID: 10434026

Max Phase: Preclinical

Molecular Formula: C23H50O4P2

Molecular Weight: 452.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCCOP(=O)([O-])OCC[P+](C)(C)C

Standard InChI:  InChI=1S/C23H50O4P2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-26-29(24,25)27-22-23-28(2,3)4/h5-23H2,1-4H3

Standard InChI Key:  LKRUUBNORFYVBG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 28  0  0  0  0  0  0  0  0999 V2000
    3.9249  -11.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278  -10.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042  -12.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3510  -11.8165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0661  -11.4069    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.7812  -10.9931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4758  -12.1179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6522  -10.6918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4964  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2073  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9183  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6293  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3444  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0595  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7747  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4856  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2007  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9075  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6227  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3378  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0488  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7639  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4790  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1942  -10.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9076  -11.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6175  -10.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139  -11.4069    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1 29  1  0
 29  3  1  0
 29  4  1  0
 29  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 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
  1  2  1  0
 27 28  1  0
M  CHG  2   9  -1  29   1
M  END

Alternative Forms

1. Parent:

   

   ALA229517

   Octadecylphosphophosphoniumcholine

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: 452.60

Molecular Weight (Monoisotopic): 452.3184

AlogP: 7.66

#Rotatable Bonds: 22

Polar Surface Area: 58.59

Molecular Species: ACID

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.91

CX Basic pKa: ┄

CX LogP: 7.54

CX LogD: 5.17

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.12

Np Likeness Score: 0.15

References

1. Obando D, Widmer F, Wright LC, Sorrell TC, Jolliffe KA..  (2007)  Synthesis, antifungal and antimicrobial activity of alkylphospholipids.,  15  (15): [PMID:17532639] [10.1016/j.bmc.2007.05.028]

Source

Source(1):

• Scientific Literature