1-(2-Methoxy-propoxy)-octadecyl-phosphinyl-oxy-N,N,N-trimethylethaniminium hydroxide hydrochloride (edelfosine) HCl

ID: ALA1204178

PubChem CID: 49861520

Max Phase: Preclinical

Molecular Formula: C27H59ClNO6P

Molecular Weight: 523.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC.Cl

Standard InChI:  InChI=1S/C27H58NO6P.ClH/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-32-25-27(31-5)26-34-35(29,30)33-24-22-28(2,3)4;/h27H,6-26H2,1-5H3;1H

Standard InChI Key:  RZCLNVCQQKXVQF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 34  0  0  0  0  0  0  0  0999 V2000
   11.0783    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  -11.1662    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4517   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7372    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0227   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4504    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0215    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5925    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6943    0.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5522    0.2004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.2121    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -0.9266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    0.5023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811   -0.6246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6956   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4101   -0.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1246   -0.2121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8390    0.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5371   -0.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7121    0.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    1.0254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    1.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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 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  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
 22 35  1  0
 35 36  1  0
M  CHG  2  27  -1  31   1
M  END

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: 523.74

Molecular Weight (Monoisotopic): 523.4002

AlogP: 6.49

#Rotatable Bonds: 27

Polar Surface Area: 77.05

Molecular Species: ACID

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.86

CX Basic pKa: ┄

CX LogP: 3.11

CX LogD: 5.13

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.07

Np Likeness Score: 0.55

References

1. Houlihan WJ, Munder PG, Handley DA, Cheon SH, Parrino VA..  (1995)  Antitumor activity of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinolines.,  38  (2): [PMID:7830265] [10.1021/jm00002a004]

Source

Source(1):

• Scientific Literature