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Compound Detail

CHEMBL269671

ARTEMISININ
🧪 Phase III
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🧪 Phase III
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@]32OO4

Basic Information

ChEMBL ID CHEMBL269671
Name ARTEMISININ
Phase Phase III
Structure Type MOL
InChI Key BLUAFEHZUWYNDE-NNWCWBAJSA-N
Therapeutic ✓ Yes

Known Names

(+)-artemisinin Artemisinin Artemisinina Artemisinine Artemisininum GNF-PF-5341 Huanghuahaosu NSC-369397 Qing hau sau
47
Targets
675
Activities
4
Assay Types
8
PK Parameters
20
Publications
9
Known Names
3
Indications
1
Mechanisms

Molecular Properties

282.3
MW (Da)
2.39
ALogP
5
HBA
0
HBD
54.0
PSA (Ų)
0.50
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product First in Class
USAN Stem arte-

Extended Properties

Molecular Formula C15H22O5
MW 282.34
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 3.84

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Indications

Malaria Schizophrenia Severe Acute Respiratory Syndrome

ATC Classification

P01BE01
artemisinin
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS

Activity Summary

IC50 588 meas. best 9.85
EC50 81 meas. best 9.1
Ki 4 meas. best 7.1
Kd 2 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
IC50 9.85 9.85 0.1 1
Plasmodium falciparum
CHEMBL364
IC50 9.22 7.9047 0.6 474
Plasmodium falciparum
CHEMBL364
EC50 9.1 8.0629 0.8 59
Plasmodium falciparum K1
CHEMBL612856
IC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
IC50 8.06 6.786 8.7 5
Plasmodium berghei
CHEMBL612653
IC50 8.05 7.25 8.9 4
NON-PROTEIN TARGET
CHEMBL3879801
IC50 8.05 5.134 9.0 10
FM3A
CHEMBL614297
EC50 8.0 5.3333 10.0 9
Unchecked
CHEMBL612545
EC50 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
Ki 7.1 6.16 79.0 2
Unchecked
CHEMBL612545
Kd 6.82 6.82 150.0 1
Cryptococcus neoformans
CHEMBL365
IC50 6.6 6.6 250.0 1
Leishmania major
CHEMBL612879
IC50 6.52 6.32 300.0 2
L02
CHEMBL4296457
IC50 6.37 5.725 430.0 2
SMMC-7721
CHEMBL613831
IC50 6.36 6.28 440.0 2
Prostaglandin E synthase 2
CHEMBL4411
Kd 6.28 6.28 530.0 1
Cytochrome P450 2B6
CHEMBL4729
EC50 6.22 6.22 600.0 1
Toxoplasma gondii
CHEMBL612888
IC50 6.19 5.945 640.0 2
Toxoplasma gondii
CHEMBL612888
EC50 6.1 5.8575 800.0 4
Molecular identity unknown
CHEMBL612546
IC50 6.0 6.0 1000.0 1
HUVEC
CHEMBL613979
IC50 5.96 5.96 1100.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.7 5.7 2000.0 1
Hepatocyte
CHEMBL613690
EC50 5.4 5.34 4000.0 2
HepG2
CHEMBL395
IC50 5.39 4.7 4090.0 2
T-cell
CHEMBL614309
IC50 5.35 5.35 4430.0 1
Cytochrome P450 2B6
CHEMBL4729
Ki 5.34 5.34 4600.0 1
Cytochrome P450 3A4
CHEMBL340
EC50 5.23 5.23 5900.0 1
HCT-116
CHEMBL394
IC50 5.14 5.14 7200.0 1
BEAS-2B
CHEMBL4296403
IC50 5.12 5.12 7530.0 1
Cytochrome P450 2B6
CHEMBL4729
IC50 5.08 5.0 8400.0 2
Prostaglandin E synthase 2
CHEMBL4411
IC50 5.06 5.0217 8800.0 6
A549
CHEMBL392
IC50 5.01 4.7467 9850.0 3
SARS-CoV-2
CHEMBL4303835
EC50 4.99 4.99 10280.0 1
SK-MEL-2
CHEMBL614917
IC50 4.89 4.89 12900.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.87 4.87 13400.0 2
Pichia kudriavzevii
CHEMBL612841
IC50 4.85 4.85 14170.0 1
SK-OV-3
CHEMBL614925
IC50 4.84 4.84 14300.0 1
XF498
CHEMBL613533
IC50 4.79 4.79 16200.0 1
HCT-15
CHEMBL612263
IC50 4.76 4.76 17200.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 4.69 4.69 20400.0 2
Cytochrome P450 3A4
CHEMBL340
Ki 4.6 4.6 25000.0 1
ADR5000 cell line
CHEMBL614266
IC50 4.57 4.57 26900.0 1
ADR5000 cell line
CHEMBL614266
EC50 4.57 4.57 26900.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 4.52 4.52 30000.0 1
Leishmania donovani
CHEMBL367
IC50 4.51 4.3525 30800.0 4
CCRF-CEM
CHEMBL382
IC50 4.43 4.43 36900.0 4
CCRF-CEM
CHEMBL382
EC50 4.43 4.43 36900.0 1
A-431
CHEMBL614069
IC50 4.41 4.41 39030.0 2
HEK293
CHEMBL614818
IC50 4.41 4.41 39030.0 1
COLO 205
CHEMBL614561
IC50 4.41 4.41 39030.0 2

Pharmacokinetic Data

Parameter Value Units Species
Cmax 1600.0 nM Homo sapiens
T1/2 2.0 hr -
T1/2 23.5 hr -
T1/2 23.5 hr -
T1/2 1.0 hr Homo sapiens
T1/2 2.0 hr Homo sapiens
T1/2 2.0 hr Homo sapiens
T1/2 24.0 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 0.14 nM 9.85 Cytotoxicity against human MCF7 cells assessed as reduction in cell number after... 28549888
Plasmodium falciparum IC50 = 0.6 nM 9.22 Antiplasmodial activity against Plasmodium falciparum Dd2 infected in human Eryt... 29360043
Plasmodium falciparum EC50 = 0.8 nM 9.1 Antiplasmodial activity against late stage (IV/V) Plasmodium falciparum NF54 gam... 27631715
Plasmodium falciparum IC50 = 0.82 nM 9.09 Antiplasmodium activity against chloroquine-resistant intraerythrocytic stage of... 25650896
Plasmodium falciparum IC50 = 0.81 nM 9.09 Antiplasmodial activity against Plasmodium falciparum D6 infected in human Eryth... 29360043
Plasmodium falciparum EC50 = 1.0 nM 9.0 Antimalarial activity against Plasmodium falciparum 3D7 assessed as reduction in... 37163950
Plasmodium falciparum IC50 = 1.0 nM 9.0 Intrinsic equimolar activity against Plasmodium falciparum W2 Indochina relative... 3279208
Plasmodium falciparum IC50 = 1.0 nM 9.0 Intrinsic equimolar activity against Plasmodium falciparum D6 (Sierra Leone) rel... 3279208
Plasmodium falciparum IC50 = 1.0 nM 9.0 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 aft... 18362073
Plasmodium falciparum K1 IC50 = 1.0 nM 9.0 OSM: Inhibition of Plasmodium falciparum K1 growth. IC50 values determined from ... -
Plasmodium falciparum EC50 = 1.0 nM 9.0 Antimalarial activity against Plasmodium falciparum K1 assessed as reduction in ... 37163950
Plasmodium falciparum IC50 = 1.26 nM 8.9 Antiplasmodial activity against Plasmodium falciparum Dd2 harboring CYTb-Qi muta... 24914738
Plasmodium falciparum IC50 = 1.29 nM 8.89 Antiplasmodial activity against Plasmodium falciparum Dd2 harboring HSP90 mutant 24914738
Plasmodium falciparum IC50 = 1.3 nM 8.89 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR I... 24914738
Plasmodium falciparum IC50 = 1.3 nM 8.89 Antiplasmodial activity against Plasmodium falciparum 7G8 harboring mutations co... 25007124
Plasmodium falciparum IC50 = 1.4 nM 8.85 Antiplasmodial activity against CQ-resistant Plasmodium falciparum FCR-3/Gambia ... 37542987
Plasmodium falciparum IC50 = 1.4 nM 8.85 Antimalarial activity against chloroquine sensitive Plasmodium falciparum FCR-3 33508479
Plasmodium falciparum IC50 = 1.51 nM 8.82 Antiplasmodial activity against Plasmodium falciparum Dd2 24914738
Plasmodium falciparum IC50 = 1.81 nM 8.74 Antiplasmodial activity against Plasmodium falciparum Dd2 harboring DHODH mutant 24914738
Plasmodium falciparum IC50 = 1.84 nM 8.73 Antiplasmodial activity against Plasmodium falciparum Dd2 harboring CRT mutant 24914738

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 464
- 10.5281/zenodo.13943903 ADMET 67
25137549 10.1021/jm5009693 Plasmodium falciparum 36
20028825 10.1128/aac.01305-09 Plasmodium falciparum 30
20160056 10.1128/aac.01636-09 Plasmodium falciparum 28
3279208 10.1021/jm00398a026 Plasmodium berghei 26
22679214 10.1124/dmd.112.045765 Hepatocyte 24
17698618 10.1128/aac.00582-07 Toxoplasma gondii 21
38287228 10.1021/acs.jmedchem.3c01989 Prostaglandin E synthase 2 20
20566762 10.1128/aac.00121-10 Plasmodium falciparum 19
8544181 10.1021/jm00026a012 Mus musculus 17
33989911 10.1016/j.ejmech.2021.113408 Plasmodium falciparum 17
27010926 10.1021/acs.jmedchem.5b01380 Plasmodium falciparum 13
17242150 10.1128/aac.00967-06 Plasmodium vinckei petteri 13
33508479 10.1016/j.ejmech.2021.113193 Plasmodium falciparum 12
20813948 10.1126/science.1193225 Plasmodium falciparum 12
24914738 10.1021/jm500535j Plasmodium falciparum 11
31216504 10.1016/j.ejmech.2019.06.018 PC-3 11
17371812 10.1128/aac.01607-06 Plasmodium falciparum 10
22679214 10.1124/dmd.112.045765 Cytochrome P450 3A4 10

Data from ChEMBL 36 via Core Engine