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Compound Detail

CHEMBL338474

HELENALIN
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C=C1C(=O)O[C@@H]2C[C@@H](C)[C@@H]3C=CC(=O)[C@@]3(C)[C@@H](O)[C@H]12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL338474
Name HELENALIN
Phase Preclinical
Structure Type MOL
InChI Key ZVLOPMNVFLSSAA-XEPQRQSNSA-N
24
Targets
52
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

262.3
MW (Da)
1.25
ALogP
4
HBA
1
HBD
63.6
PSA (Ų)
0.53
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H18O4
MW 262.30
Aromatic Rings 0
Heavy Atoms 19
NP-Likeness 3.82

Activity Summary

IC50 47 meas. best 6.68
EC50 5 meas. best 6.38

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SK-LU-1
CHEMBL614913
 IC50 6.68 6.68 210.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.64 6.64 230.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.57 6.09 270.0 9
K562
CHEMBL385
 IC50 6.55 6.55 280.0 1
HCT-15
CHEMBL612263
 IC50 6.54 6.54 290.0 1
HL-60
CHEMBL383
 IC50 6.5 6.33 320.0 2
E3 ubiquitin-protein ligase Mdm2
CHEMBL5023
 EC50 6.38 6.38 420.0 1
Jurkat
CHEMBL397
 IC50 6.34 6.165 460.0 2
MCF7
CHEMBL387
 IC50 6.3 6.1867 500.0 3
HeLa
CHEMBL399
 EC50 6.16 6.16 700.0 1
ZR-75-1
CHEMBL614393
 IC50 6.16 6.0733 700.0 3
HEp-2
CHEMBL614735
 IC50 6.1 6.0667 800.0 3
A-431
CHEMBL614069
 IC50 6.1 6.0667 800.0 3
SW872
CHEMBL2366302
 IC50 5.92 5.8967 1200.0 3
OVCAR-3
CHEMBL614213
 IC50 5.85 5.8067 1400.0 3
Transcriptional activator Myb
CHEMBL2380186
 IC50 5.62 5.62 2370.0 2
X-box-binding protein 1
CHEMBL1741176
 IC50 5.61 5.61 2430.0 1
Unchecked
CHEMBL612545
 IC50 5.6 5.51 2500.0 2
DNA damage-inducible transcript 3 protein
CHEMBL2146304
 IC50 5.58 5.58 2610.0 1
G-protein coupled receptor 55
CHEMBL1075322
 IC50 5.58 5.58 2642.3 1
Telomerase reverse transcriptase
CHEMBL2916
 IC50 5.4 5.4 4000.0 2
Platelet
CHEMBL4296519
 IC50 5.37 5.37 4280.0 1
Unchecked
CHEMBL612545
 EC50 5.33 5.17 4625.0 3
Type-1 angiotensin II receptor
CHEMBL227
 IC50 4.73 4.73 18639.0 1
ADMET
CHEMBL612558
 IC50 4.68 4.68 21110.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SK-LU-1 IC50 = 210.0 nM 6.68 Cytotoxicity against human SKLU1 cells assessed as growth inhibition after 48 hr... 22574648
Plasmodium falciparum IC50 = 230.0 nM 6.64 Antimalarial activity against Plasmodium falciparum 19299148
NON-PROTEIN TARGET IC50 = 270.0 nM 6.57 Cytotoxicity against human GTB cells after 5 hrs by MTT assay 10425121
K562 IC50 = 280.0 nM 6.55 Cytotoxicity against human K562 cells assessed as growth inhibition after 48 hrs... 22574648
HCT-15 IC50 = 290.0 nM 6.54 Cytotoxicity against human HCT15 cells assessed as growth inhibition after 48 hr... 22574648
HL-60 IC50 = 320.0 nM 6.5 Cytotoxicity against human HL-60 cells after 5 hrs by MTT assay 10425121
NON-PROTEIN TARGET IC50 = 390.0 nM 6.41 Cytotoxicity against mouse cloned EN2 cells after 72 hrs by MTT assay 9090867
E3 ubiquitin-protein ligase Mdm2 EC50 = 420.0 nM 6.38 PUBCHEM_BIOASSAY: E3 Ligase dose-response_384. (Class of assay: confirmatory) [R... -
Jurkat IC50 = 460.0 nM 6.34 Cytotoxicity against human Jurkat T cells after 20 hrs by WST1 assay 16499337
NON-PROTEIN TARGET IC50 = 500.0 nM 6.3 Cytotoxicity against human SK MEL28 cells after 72 hrs by [3H]thymidine incorpor... 10425121
MCF7 IC50 = 500.0 nM 6.3 Cytotoxicity against human MCF7 cells after 48 hrs by [3H]thymidine incorporatio... 10425121
HL-60 IC50 = 700.0 nM 6.16 Cytotoxicity against human HL60 after 20 hrs by WST1 assay 16499337
MCF7 IC50 = 700.0 nM 6.16 Cytotoxicity against human MCF7 cells after 72 hrs by [3H]thymidine incorporatio... 10425121
NON-PROTEIN TARGET IC50 = 700.0 nM 6.16 Cytotoxicity against human SK37 cells after 72 hrs by [3H]thymidine incorporatio... 10425121
ZR-75-1 IC50 = 700.0 nM 6.16 Cytotoxicity against human ZR-75-1 cells after 24 hrs by [3H]thymidine incorpora... 10425121
HeLa EC50 = 700.0 nM 6.16 Cytotoxicity against human HeLa cells by MTT assay 28958621
HEp-2 IC50 = 800.0 nM 6.1 Cytotoxicity against human HEP2 cells after 72 hrs by [3H]thymidine incorporatio... 10425121
A-431 IC50 = 800.0 nM 6.1 Cytotoxicity against human A431 cells after 72 hrs by [3H]thymidine incorporatio... 10425121
MCF7 IC50 = 800.0 nM 6.1 Cytotoxicity against human MCF7 cells after 24 hrs by [3H]thymidine incorporatio... 10425121
ZR-75-1 IC50 = 800.0 nM 6.1 Cytotoxicity against human ZR-75-1 cells after 48 hrs by [3H]thymidine incorpora... 10425121

Literature References

PubMed DOI Target Context # Activities
845864 10.1021/jm00213a003 Ehrlich 13
7328595 10.1021/jm00140a003 Mus musculus 10
10425121 10.1021/np990058v NON-PROTEIN TARGET 7
845864 10.1021/jm00213a003 Unchecked 6
845864 10.1021/jm00213a003 No relevant target 3
10425121 10.1021/np990058v OVCAR-3 3
10425121 10.1021/np990058v MCF7 3
10425121 10.1021/np990058v HEp-2 3
10425121 10.1021/np990058v A-431 3
10425121 10.1021/np990058v SW872 3
10425121 10.1021/np990058v ZR-75-1 3
16499337 10.1021/np0504513 Jurkat 2
17336532 10.1016/j.bmc.2007.02.005 KB 2
9090867 10.1021/np960517h NON-PROTEIN TARGET 2
23501116 10.1016/j.ejmech.2013.02.018 Transcriptional activator Myb 2
11052798 10.1021/jm000058o Unchecked 2
18157122 10.1038/nchembio.2007.59 Janus Kinase (JAK) 2
- 10.1039/C0MD00241K Telomerase reverse transcriptase 2
17150968 10.1074/jbc.m606728200 Unchecked 1
- 10.6019/CHEMBL4296183 Candida albicans 1

Data from ChEMBL 36 via Core Engine