(R)-{2-[Hydroxy-(2-methoxy-3-octadecyloxy-propoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium

ID: ALA107514

Chembl Id: CHEMBL107514

Cas Number: 77286-66-9

PubChem CID: 6918215

Product Number: Y42952

Max Phase: Preclinical

Molecular Formula: C27H58NO6P

Molecular Weight: 523.74

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Edelfosine | ET-18-OCH3|77286-66-9|(R)-edelfosine|1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphocholine|Edelfosine, (R)-|LZ198HY9OE|TLC-ELL-12|CHEBI:78653|[(2R)-2-methoxy-3-octadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate|1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphorylcholine|1-Stearyl-2-methyl-sn-glycero-3-phosphocholine|3,5,9-Trioxa-4-phosphaheptacosan-1-aminium, 4-hydroxy-7-methoxy-N,N,N-trimethyl-, inner salt, 4-oxide, (7R)-|3,5,9-Trioxa-4-phosphaheptacosan-1-aminium, 4-hydroxy-7-methShow More⌵

Canonical SMILES:  CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC

Standard InChI:  InChI=1S/C27H58NO6P/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/t27-/m1/s1

Standard InChI Key:  MHFRGQHAERHWKZ-HHHXNRCGSA-N

Alternative Forms

1. Parent:

   

   ALA107514

   (R)-EDELFOSINE

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. Hong CI, An SH, Buchheit DJ, Nechaev A, Kirisits AJ, West CR, Berdel WE..  (1986)  Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids.,  29  (10): [PMID:3761322] [10.1021/jm00160a041]

2. Marino-Albernas JR, Bittman R, Peters A, Mayhew E..  (1996)  Synthesis and growth inhibitory properties of glycosides of 1-O-hexadecyl-2-O-methyl-sn-glycerol, analogs of the antitumor ether lipid ET-18-OCH3 (edelfosine).,  39  (17): [PMID:8765506] [10.1021/jm960164j]

3. Batista J, Friedrichson T, Schlechtingen G, Braxmeier T, Jennings G, Bajorath J..  (2010)  Computational screening for membrane-directed inhibitors of mast cell activation.,  45  (6): [PMID:20153565] [10.1016/j.ejmech.2010.01.061]

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. de Lucio H, Gamo AM, Ruiz-Santaquiteria M, de Castro S, Sánchez-Murcia PA, Toro MA, Gutiérrez KJ, Gago F, Jiménez-Ruiz A, Camarasa MJ, Velázquez S..  (2017)  Improved proteolytic stability and potent activity against Leishmania infantum trypanothione reductase of α/β-peptide foldamers conjugated to cell-penetrating peptides.,  140  [PMID:29017116] [10.1016/j.ejmech.2017.09.032]

10. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Fraunhofer HDAC6