Artemisinin (CED0001741)

Record Information

Version

1.0

Creation Date

2016-05-22 04:27:57 UTC

Update Date

2026-05-14 19:30:25 UTC

Accession Number

CHEM017564

Identification

Common Name

Artemisinin

Class

Small Molecule

Description

Artemisinin (C15H22O5) is a compound with an average molecular weight of 282.34 g/mol. Artemisinin belongs to the terpene lactones, a subclass of prenol lipids within the organic compounds. Biologically, it functions as a drug (PMC9495708), an antioxidant (PMC9495708), and an antimalarial (PMC3768262, PMC4344607). Industrially, it is used as a biocide and as a softener and conditioner. It acts as an inhibitor of the mitochondrial protein target Dihydroorotate dehydrogenase (quinone). The compound is used in the treatment of malaria (PMC11832355, PMC7793148, PMC9495708), cancer (PMC10059971), and fever (PMC7833388). Additionally, it has a therapeutic effect on polycystic ovary syndrome (PMC12947462). Artemisinin is found in or released from 22 recorded sources across several sectors. These include healthcare, pharmaceuticals & veterinary products via medical devices; drinking water & water supply via drinking water; textiles, leather & furnishings such as carpets, rugs, and synthetic textiles; household cleaning & consumer products including pipe accessories, tobacco pipes, and cigar cigarettes; food, food processing & cookware including food packaging and the preparation of vinegar, wort, and fermentation processes for beer; and electrical & electronic equipment such as batteries, capacitors, printed circuit boards, wires, cables, and cell phones, among three more sectors. Recorded routes of exposure include oral, inhalation, and touch.

Contaminant Type

Human Neurotoxin
PFAS
Phytotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,5,9-Trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one	ChEBI
Arteannuin	ChEBI
Artemisinina	ChEBI
Artemisinine	ChEBI
Artemisininum	ChEBI
Huanghuahaosu	ChEBI
Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-J)-1,2-benzodioxepin-10(3H)-one	ChEBI
QHS	ChEBI
Qing hau sau	ChEBI
Qinghaosu	ChEBI
Quing hau sau	ChEBI
Quinghaosu	MeSH
Artemisinin	ChEBI

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Mass

282.336 g/mol

Monoisotopic Mass

282.147 g/mol

CAS Registry Number

63968-64-9

IUPAC Name

(1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-one

Traditional Name

(+)-artemisinin

SMILES

[H][C@@]1(C)CC[C@@]2([H])[C@@]([H])(C)C(=O)O[C@]3([H])O[C@@]4(C)CC[C@]1([H])[C@@]23OO4

InChI Identifier

InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

InChI Key

BLUAFEHZUWYNDE-NNWCWBAJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Artemisinin skeleton
Terpene lactone
Sesquiterpenoid
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
1,2,4-trioxane
Carboxylic acid ester
Lactone
Dialkyl peroxide
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic peroxide (CHEBI:223316 )
sesquiterpene lactone (CHEBI:223316 )
Eudesmane sesquiterpenoids (C09538 )
Sesquiterpenoids (C15) (C09538 )
Eudesmane sesquiterpenoids (LMPR0103190003 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.27 g/L	ALOGPS
logP	2.52	ALOGPS
logP	3.11	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.68 m³·mol⁻¹	ChemAxon
Polarizability	29.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum	splash10-0007-0901000000-4fa10fe72dc24b85ac9c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-014i-0190000000-3391c971e951545100ee	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ldj-0960000000-ff3a9e18db5c8c53bcb4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01wb-0910000000-42c2b516c8462b3dd492	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01x1-0900000000-5c3e44b5d52be3adbba2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a7l-0900000000-01583256dc6d13c1315f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a59-0900000000-189290ae52e9283563ba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0090000000-81624c4cf74214fdaa9f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1090000000-280b3ca0132072b52506	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05mo-9100000000-73e8efda73cc4b76c149	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001r-0090000000-f9b1c888e060cd130d8c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0019-1090000000-53e88c0fa4a2405b229c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4690000000-687f2a3a4ca745522896	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2395.0	Log mg/kg	[1300:4300]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference
cancer	is_treatment_for	Not Available	PMC10059971
malaria	is_treatment_for	Not Available	PMC11832355 , PMC7793148 , PMC9495708
polycystic ovary syndrome	has_therapeutic_effect_on	Not Available	PMC12947462
fever	is_treatment_for	Not Available	PMC7833388

Exposure Sources

Source ID	Source	Sector	Reference
7	Pesticides	Agriculture & land management	Not Available
115	Drinking water	Drinking water & water supply	Not Available
120	Wires and cables	Electrical & Electronic Equipment	Not Available
121	Printed circuit boards	Electrical & Electronic Equipment	Not Available
125	Batteries	Electrical & Electronic Equipment	Not Available
130	Semiconductors	Electrical & Electronic Equipment	Not Available
138	Lubricants	Energy, oil & gas	Not Available
147	Food packaging	Food, food processing & cookware	Not Available
174	Lubricants	Industrial manufacturing & chemical processing	Not Available
234	Medical devices	Healthcare, pharmaceuticals & veterinary products	Not Available
451	Carpets and Rugs	Textiles, leather & furnishings	Not Available
454	Synthetic textiles	Textiles, leather & furnishings	Not Available
490		Personal care & cosmetics	Not Available
492	Cell phones	Electrical & Electronic Equipment	Not Available
493	Capacitors	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
544	Fermentation Processes For Beer	Food, food processing & cookware	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
550	Preparation Of Wort	Food, food processing & cookware	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available
566	Tobacco Pipes	Household cleaning & consumer products	Not Available
578	Making Cigars	Industrial manufacturing & chemical processing	Not Available
584	Buoys	Marine, shipping & aquaculture	Not Available
602	Molluscicides	Agriculture & land management	Not Available
604	Pest Attractants	Agriculture & land management	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	451.681
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	442.028
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	31.4511
Click to view 3D structure	PCNA-associated factor	Q15004	Humans	Predicted (SEA)	4.67095
Click to view 3D structure	Dihydroorotate dehydrogenase	Q54A96	Plasmodium falciparum	Predicted (SEA)	4.20386
Click to view 3D structure	Dihydroorotate dehydrogenase (fumarate)	P28272	Saccharomyces cerevisiae S288c	Predicted (SEA)	0.389246
Click to view 3D structure	Prostaglandin E synthase 2	Q9H7Z7	Humans	Predicted (SEA)	4.04816
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	50.7577
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	341.213
Click to view 3D structure	Ferritin heavy chain	P02794	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Serine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoform	Q76MZ3	Mus musculus	Predicted (SEA)	0.778492
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	78.1606
Click to view 3D structure	Sex hormone-binding globulin	P08689	Rattus norvegicus	Predicted (SEA)	20.2408
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	48.6558
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	2574.47
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	2330.18
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	1113.4
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	204.199
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	1763.44
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	2766.84
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	1465.51
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	3440.0
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	6434.08
Click to view 3D structure	Glucose-6-phosphate 1-dehydrogenase	Q9GRG7	Trypanosoma brucei	Predicted (SEA)	30.3612
Click to view 3D structure	E3 ubiquitin-protein ligase ZFP91	Q96JP5	Humans	Predicted (SEA)	31.996