General
Preferred name
EDELFOSINE
Synonyms
ET-18-OCH3 ()
NSC-343649 ()
Edelfosina ()
NSC-324368 ()
ET-18-OME ()
Edelfosine ()
P&D ID
PD011196
CAS
119225-10-4
70641-51-9
Tags
available
drug candidate
Drug Status
investigational
Max Phase
2.0
Structure
PD011196
EDELFOSINE
RO5
MW
523.4
HBA
6
HBD
0
RB
27
LOGP
6.49
6742
5
0
3
Structure formats
SMILES
CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
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
InChIkey
MHFRGQHAERHWKZ-UHFFFAOYSA-N
MOL
EDELFOSINE RDKit 2D 35 34 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0933 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6913 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2894 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.8875 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.4856 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.7846 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.0836 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.3827 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 24.6817 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 25.9808 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 27.2798 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 28.5788 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 29.8779 0.7500 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 29.1279 2.0490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 30.6279 -0.5490 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0 31.1769 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 31.1769 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 32.4760 3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 32.4760 5.2500 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0 33.9760 5.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 30.9760 5.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 32.4760 6.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 25.9808 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 27.2798 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 10 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 2 0 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 30 33 1 0 21 34 1 0 34 35 1 0 M CHG 2 26 -1 30 1 M END > <ID> PD011196 > <Name> EDELFOSINE
Protein targets
3
5.75
PTAFR Platelet-activating factor receptor
5
1
5.46
AKT1 RAC-alpha serine/threonine-protein kinase CELL-BASED 3.5x
42
1
4.92
PRKCA,PRKCB,... Protein kinase C (PKC)
0
1
Target pathways
47
Activation of BAD and translocation to mitochondria
R-HSA-111447
AKT1
AKT phosphorylates targets in the cytosol
R-HSA-198323
AKT1
AKT phosphorylates targets in the nucleus
R-HSA-198693
AKT1
AKT-mediated inactivation of FOXO1A
R-HSA-211163
AKT1
Butyrate Response Factor 1 (BRF1) binds and destabilizes mRNA
R-HSA-450385
AKT1
CD28 dependent PI3K/Akt signaling
R-HSA-389357
AKT1
Class A/1 (Rhodopsin-like receptors)
R-HSA-373076
PTAFR
Co-inhibition by CTLA4
R-HSA-389513
AKT1
Constitutive Signaling by AKT1 E17K in Cancer
R-HSA-5674400
AKT1
Cyclin A:Cdk2-associated events at S phase entry
R-HSA-69656
AKT1
Cyclin E associated events during G1/S transition
R-HSA-69202
AKT1
Deactivation of the beta-catenin transactivating complex
R-HSA-3769402
AKT1
Downregulation of ERBB2:ERBB3 signaling
R-HSA-1358803
AKT1
eNOS activation
R-HSA-203615
AKT1
Estrogen-dependent nuclear events downstream of ESR-membrane signaling
R-HSA-9634638
AKT1
Extra-nuclear estrogen signaling
R-HSA-9009391
AKT1
FLT3 Signaling
R-HSA-9607240
AKT1
G alpha (q) signalling events
R-HSA-416476
PTAFR
G beta:gamma signalling through PI3Kgamma
R-HSA-392451
AKT1
High laminar flow shear stress activates signaling by PIEZO1 and PECAM1:CDH5:KDR in endothelial cells
R-HSA-9856530
AKT1
Integrin signaling
R-HSA-354192
AKT1
Interferon gamma signaling
R-HSA-877300
PTAFR
Interleukin-10 signaling
R-HSA-6783783
PTAFR
Interleukin-4 and Interleukin-13 signaling
R-HSA-6785807
AKT1
KEAP1-NFE2L2 pathway
R-HSA-9755511
AKT1
KSRP (KHSRP) binds and destabilizes mRNA
R-HSA-450604
AKT1
Mechanical load activates signaling by PIEZO1 and integrins in osteocytes
R-HSA-9856532
AKT1
Mitochondrial unfolded protein response (UPRmt)
R-HSA-9841251
AKT1
MTOR signalling
R-HSA-165159
AKT1
Negative regulation of NOTCH4 signaling
R-HSA-9604323
AKT1
Negative regulation of the PI3K/AKT network
R-HSA-199418
AKT1
Neutrophil degranulation
R-HSA-6798695
PTAFR
PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling
R-HSA-6811558
AKT1
PIP3 activates AKT signaling
R-HSA-1257604
AKT1
PTK6 Regulates RTKs and Their Effectors AKT1 and DOK1
R-HSA-8849469
AKT1
RAB GEFs exchange GTP for GDP on RABs
R-HSA-8876198
AKT1
Regulation of localization of FOXO transcription factors
R-HSA-9614399
AKT1
Regulation of PTEN stability and activity
R-HSA-8948751
AKT1
Regulation of TP53 Activity through Acetylation
R-HSA-6804758
AKT1
Regulation of TP53 Activity through Association with Co-factors
R-HSA-6804759
AKT1
Regulation of TP53 Degradation
R-HSA-6804757
AKT1
RUNX2 regulates genes involved in cell migration
R-HSA-8941332
AKT1
SARS-CoV-2 targets host intracellular signalling and regulatory pathways
R-HSA-9755779
AKT1
Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation
R-HSA-1474151
AKT1
TP53 Regulates Metabolic Genes
R-HSA-5628897
AKT1
Translocation of SLC2A4 (GLUT4) to the plasma membrane
R-HSA-1445148
AKT1
VEGFR2 mediated vascular permeability
R-HSA-5218920
AKT1
References
15
2023 Design, synthesis, and repurposing of O<sup>6</sup>-aminoalkyl-sulfuretin analogs towards discovery of potential lead compounds as antileishmanial agents.
Hassan AHE, Phan TN et al. Eur J Med Chem
2020 Pre-clinical evidences of the antileishmanial effects of diselenides and selenocyanates.
Garnica P,Etxebeste-Mitxeltorena M et al. Bioorg Med Chem Lett
2020 Tellurides Bearing Sulfonamides as Novel Inhibitors of Leishmanial Carbonic Anhydrase with Potent Antileishmanial Activity.
Angeli A, Etxebeste-Mitxeltorena M et al. J Med Chem
2018 Trypanothione reductase inhibition and anti-leishmanial activity of all-hydrocarbon stapled α-helical peptides with improved proteolytic stability.
Ruiz-Santaquiteria M, de Castro S et al. Eur J Med Chem
2018 Induction of cell killing and autophagy by amphiphilic pyrrolidine derivatives on human pancreatic cancer cells.
Bello C, Bai J et al. Eur J Med Chem
2014 Novel hybrid selenosulfonamides as potent antileishmanial agents.
Baquedano Y, Moreno E et al. Eur. J. Med. Chem.
2013 Synthesis, characterization and Akt phosphorylation inhibitory activity of cyclopentanecarboxylate-substituted alkylphosphocholines.
Alam MM, Joh EH et al. Bioorg. Med. Chem.
2011 Selenocyanates and diselenides: a new class of potent antileishmanial agents.
Plano D, Baquedano Y et al. Eur. J. Med. Chem.
2008 Characterization of an ABCG-like transporter from the protozoan parasite Leishmania with a role in drug resistance and transbilayer lipid movement.
Castanys-Muñoz E, Pérez-Victoria JM et al. Antimicrob. Agents Chemother.
2005 Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue.
Andresen TL, Jensen SS et al. J. Med. Chem.
1997 Imidazole and triazole substituted ether phospholipids: potent antitumor agents
Nair HK, Peterson AC et al. Bioorg. Med. Chem. Lett.
1995 Synthesis of alkyl chain-modified ether lipids and evaluation of their in vitro cytotoxicity.
Fos E, Suesa N et al. J. Med. Chem.
1991 In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents.
Meyer KL, Marasco CJ et al. J. Med. Chem.
1991 Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity.
Piantadosi C, Marasco CJ et al. J. Med. Chem.
1990 Synthesis of quaternary amine ether lipids and evaluation of neoplastic cell growth inhibitory properties.
Morris-Natschke SL, Meyer KL et al. J. Med. Chem.
Cell lines
13
5.7
HL-60
5.7
HT-29
5.3
MDA-MB-231
5.3
THP-1
5.21
K562
5.13
A549
5.03
MCF7
4.92
MDA-MB-435
4.91
Jurkat
4.87
A-431
4.73
BXPC-3
4.59
PANC-1
4.35
FHC
Organisms
3
6.09
Leishmania infantum
5.4
Human immunodeficiency virus 1
5.11
Leishmania donovani
Compound Sets
5
ChEMBL Drugs
CHEMBL28509
DrugMatrix
MedChem Express Bioactive Compound Library
HY-108610A
NIH Mechanistic Set
NPC Screening Collection
Available from
3
Mcule
MCULE-3074032746
MedChem Express Bioactive Compound Library
HY-108610A
MolPort
Molport-049-227-001
External IDs
19
ChEMBL CHEMBL28509
PubChem 1392
ACToR 119225-10-4
BindingDB 50011796
Brenda 154086
ChEBI 78652
ChemSpider 1350
COCONUT CNP0578385.0
eMolecules 1937830
FDA SRS 1Y6SNA8L5S
GSRS b150d8b2-a4ee-4...
HMDB HMDB0251700
IBM NIH 2B94B8B1B29633A...
Mcule MCULE-3074032746
MolPort Molport-049-227-001
PubChem DOTF 12012922
PubChem TPS 14934159
Reactome 1350
SureChEMBL SCHEMBL52069
Properties
(calculated by RDKit )
Molecular Weight
523.4
Hydrogen Bond Acceptors
6
Hydrogen Bond Donors
0
Rotatable Bonds
27
Ring Count
0
Aromatic Ring Count
0
cLogP
6.49
TPSA
77.05
Fraction CSP3
1.0
Chiral centers
2.0
Largest ring
0.0
QED
0.07
Structural alerts
0
No structural alerts detected
Custom attributes
(extracted from source data)
Pathway
Apoptosis
Source data