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Compound Detail

CHEMBL28509

EDELFOSINE
🧪 Phase II
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🧪 Phase II
CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL28509
Name EDELFOSINE
Phase Phase II
Structure Type MOL
InChI Key MHFRGQHAERHWKZ-UHFFFAOYSA-N

Known Names

Edelfosina Edelfosine ET-18-OME NSC-324368 NSC-343649
21
Targets
44
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names

Molecular Properties

523.7
MW (Da)
6.49
ALogP
6
HBA
0
HBD
77.0
PSA (Ų)
0.07
QED
2
Ro5 Violations
27
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Racemic

Flags

Natural Product
USAN Stem -fos-; -fosine

Extended Properties

Molecular Formula C27H58NO6P
MW 523.74
Aromatic Rings 0
Heavy Atoms 35
NP-Likeness 0.55

Activity Summary

IC50 41 meas. best 6.09
EC50 3 meas. best 6.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania infantum
CHEMBL612848
 EC50 6.22 5.635 600.0 2
Leishmania donovani
CHEMBL367
 IC50 6.09 5.5775 820.0 4
Leishmania infantum
CHEMBL612848
 IC50 6.09 5.5475 820.0 8
Human immunodeficiency virus 1
CHEMBL378
 IC50 6.04 5.72 920.0 2
HL-60
CHEMBL383
 IC50 6.0 5.6367 1000.0 3
THP-1
CHEMBL614245
 EC50 6.0 6.0 1000.0 1
Platelet-activating factor receptor
CHEMBL5136
 IC50 5.75 5.75 1800.0 1
HT-29
CHEMBL384
 IC50 5.7 5.7 2000.0 1
Unchecked
CHEMBL612545
 IC50 5.6 5.6 2500.0 1
MDA-MB-435
CHEMBL614697
 IC50 5.52 5.22 3000.0 2
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 IC50 5.46 5.46 3500.0 1
THP-1
CHEMBL614245
 IC50 5.31 5.3025 4900.0 4
MDA-MB-231
CHEMBL400
 IC50 5.3 5.3 5000.0 1
K562
CHEMBL385
 IC50 5.21 5.21 6100.0 1
A549
CHEMBL392
 IC50 5.13 5.13 7400.0 1
MCF7
CHEMBL387
 IC50 5.03 5.03 9300.0 1
Protein kinase C (PKC)
CHEMBL2093867
 IC50 4.92 4.92 12000.0 1
Jurkat
CHEMBL397
 IC50 4.91 4.91 12200.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.89 4.89 12800.0 1
A-431
CHEMBL614069
 IC50 4.87 4.87 13500.0 1
BXPC-3
CHEMBL614530
 IC50 4.73 4.73 18800.0 1
PANC-1
CHEMBL614139
 IC50 4.59 4.59 25700.0 1
FHC
CHEMBL614654
 IC50 4.35 4.35 45000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania infantum EC50 = 600.0 nM 6.22 Antileishmanial activity against Leishmania infantum MCAN/ES/89/IPZ229/1/89 axen... 29501944
Leishmania infantum IC50 = 820.0 nM 6.09 Antileishmanial activity against Leishmania infantum MCAN/ES/89/IPZ229/1/89 amas... 21571403
Leishmania infantum IC50 = 820.0 nM 6.09 Leishmanicidal activity against axenic amastigote stage of Leishmania infantum a... 24448421
Leishmania donovani IC50 = 820.0 nM 6.09 Antileishmanial activity against Leishmania donovani axenic amastigotes assessed... 32223141
Leishmania infantum IC50 = 820.0 nM 6.09 Antileishmanial activity against axenic amastigote state of Leishmania infantum ... 32738977
Human immunodeficiency virus 1 IC50 = 920.0 nM 6.04 In vitro inhibition of HIV-1 plaque formation 2016713
THP-1 EC50 = 1000.0 nM 6.0 Cytotoxicity against human THP1 cells assessed as reduction in cell viability af... 29501944
HL-60 IC50 = 1000.0 nM 6.0 Antiproliferative activity of compound was measured on human tumor cell line HL-... 7707324
Platelet-activating factor receptor IC50 = 1800.0 nM 5.75 PAF agonism was measured as the IC50 for aggregation of washed rabbit platelets ... 7707324
HL-60 IC50 = 2000.0 nM 5.7 In vitro inhibition of HL-60 human promyelocytic leukemia cell proliferation -
Leishmania donovani IC50 = 2000.0 nM 5.7 Antileishmanial activity against Leishmania donovani amastigotes infected in hum... 36944273
HT-29 IC50 = 2000.0 nM 5.7 In vitro inhibition of the HT-29 transformed human colon cell proliferation -
Unchecked IC50 = 2500.0 nM 5.6 Compounds were evaluated for antineoplastic activity against WHEI-3B cells using... 8423601
MDA-MB-435 IC50 = 3000.0 nM 5.52 Inhibition of Akt phosphorylation in MDA-MB-435 cells after 2 hrs 16279790
Leishmania infantum IC50 = 3100.0 nM 5.51 Leishmanicidal activity against amastigote stage of Leishmania infantum expressi... 24448421
RAC-alpha serine/threonine-protein kinase IC50 = 3500.0 nM 5.46 Inhibition of Akt phosphorylation in human insulin-stimulated A549 cells incubat... 23415083
Leishmania infantum IC50 = 3650.0 nM 5.44 Antileishmanial activity against Leishmania infantum MCAN/ES/89/IPZ229/1/89 prom... 21571403
Leishmania donovani IC50 = 3900.0 nM 5.41 Antileishmanial activity against Leishmania donovani promastigotes assessed as p... 36944273
Human immunodeficiency virus 1 IC50 = 4000.0 nM 5.4 In vitro inhibition of CEM-SS cell growth by 50 % 2016713
Leishmania infantum IC50 = 4800.0 nM 5.32 Antileishmanial activity against GFP-tagged at NH2 terminus Leishmania infantum ... 18644961

Literature References

PubMed DOI Target Context # Activities
29547833 10.1016/j.ejmech.2018.02.086 BXPC-3 19
29547833 10.1016/j.ejmech.2018.02.086 MIA PaCa-2 10
2308148 10.1021/jm00165a016 Protein kinase C (PKC) 7
8423601 10.1021/jm00054a017 NON-PROTEIN TARGET 7
29547833 10.1016/j.ejmech.2018.02.086 PANC-1 7
18644968 10.1128/aac.01665-07 Leishmania infantum 7
29547833 10.1016/j.ejmech.2018.02.086 Unchecked 6
17532639 10.1016/j.bmc.2007.05.028 ADMET 6
29547833 10.1016/j.ejmech.2018.02.086 PK9 6
29547833 10.1016/j.ejmech.2018.02.086 Fibroblast 6
24681987 10.1016/j.ejmech.2014.03.057 BT-474 5
36944273 10.1016/j.ejmech.2023.115256 Leishmania donovani 5
18644961 10.1128/aac.00587-08 Leishmania infantum 3
21571403 10.1016/j.ejmech.2011.04.054 Leishmania infantum 3
8336340 10.1021/jm00066a011 HL-60 3
2016713 10.1021/jm00108a021 Human immunodeficiency virus 1 3
28431354 10.1016/j.ejmech.2017.04.020 Leishmania infantum 2
29501944 10.1016/j.ejmech.2018.02.071 Leishmania infantum 2
21571403 10.1016/j.ejmech.2011.04.054 ADMET 2
7707324 10.1021/jm00007a018 HL-60 2

Data from ChEMBL 36 via Core Engine