N,N,N-trimethyl-2-{[(nonylamino-6'-oxohexyl)oxy]-hydroxyphosphinyloxy}ethanaminium inner salt

ID: ALA229244

PubChem CID: 44424400

Max Phase: Preclinical

Molecular Formula: C20H43N2O5P

Molecular Weight: 422.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCNC(=O)CCCCCOP(=O)([O-])OCC[N+](C)(C)C

Standard InChI:  InChI=1S/C20H43N2O5P/c1-5-6-7-8-9-10-13-16-21-20(23)15-12-11-14-18-26-28(24,25)27-19-17-22(2,3)4/h5-19H2,1-4H3,(H-,21,23,24,25)

Standard InChI Key:  ZVUHIAWPPASGNQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   -2.9021  -16.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1880  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121  -16.1186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1988  -15.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3221  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0212  -16.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4780  -16.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639  -16.1186    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0498  -15.7054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3547  -16.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1772  -15.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6644  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7944  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367  -16.1186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6467  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3607  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0666  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7807  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4949  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2048  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9190  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6330  -16.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3473  -15.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225  -14.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  2  0
  9 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
 17 28  2  0
M  CHG  2   3   1  10  -1
M  END

Alternative Forms

1. Parent:

   

   ALA229244

   [6-(Nonylamino)-6-oxohexyl] 2-(trimethylazaniumyl)ethyl phosphate

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: 422.55

Molecular Weight (Monoisotopic): 422.2910

AlogP: 3.62

#Rotatable Bonds: 19

Polar Surface Area: 87.69

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.88

CX Basic pKa: ┄

CX LogP: -0.55

CX LogD: 1.47

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.20

Np Likeness Score: 0.16

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