Artesunate (CED0002372)

Record Information

Version

1.0

Creation Date

2016-05-22 04:41:22 UTC

Update Date

2026-05-14 19:04:29 UTC

SynCED ID

CED0002372

Secondary Accession Numbers

CHEM017845

Identification

Common Name

Artesunate

Class

Small Molecule

Description

Artesunate is an organic compound with the formula C19H28O8 and an average molecular weight of 384.43 g/mol. Artesunate belongs to the sesquiterpenoids, a subclass of prenol lipids within the organic compounds. This compound is found in healthcare, pharmaceuticals, and veterinary products as an antiprotozoal agent, with recorded exposure routes including parenteral and intravenous administration. Mechanistically, it acts as an inhibitor of the malaria protein EXP-1.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Artesunic acid	Generator
Dihydroartemisinine-12-alpha-succinate	MeSH
Sodium artesunate	MeSH
Dihydroartemisinine 12 alpha succinate	MeSH
Succinyl dihydroartemisinin	MeSH
Dihydroartemisinin, succinyl	MeSH
Malartin	MeSH
Malacef	MeSH
Artesunate	MeSH
4-oxo-4-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-yl]oxy}butanoate	Generator

Chemical Formula

C₁₉H₂₈O₈

Average Molecular Mass

384.425 g/mol

Monoisotopic Mass

384.178 g/mol

CAS Registry Number

88495-63-0

IUPAC Name

4-oxo-4-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-yl]oxy}butanoic acid

Traditional Name

4-oxo-4-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0⁴,¹³.0⁸,¹³]hexadecan-10-yl]oxy}butanoic acid

SMILES

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

InChI Identifier

InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16+,17-,18-,19-/m1/s1

InChI Key

FIHJKUPKCHIPAT-NKHDUEHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as artemisinins. These are sesquiterpenoids originally isolated from the herb Artemisia annua. Their structure is based on artemisinin, a tetracyclic compound that contains a 1,2-dioxepane fused to an octahydrobenzopyran moiety. The internal peroxide bridge is believed to be a key to the mode of action of artemisinins.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Artemisinins

Alternative Parents

Substituents

Artemisinin skeleton
Fatty acid ester
Heterocyclic fatty acid
Oxepane
Dicarboxylic acid or derivatives
Oxane
Fatty acyl
1,2,4-trioxane
Carboxylic acid ester
Dialkyl peroxide
Oxacycle
Carboxylic acid
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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

Not Available

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	0.68 g/L	ALOGPS
logP	2.35	ALOGPS
logP	3.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.95 m³·mol⁻¹	ChemAxon
Polarizability	38.91 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kr-2459000000-709f5cba7340e7cb0802	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-7392000000-6aade85a0d3ce77db50e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-9050000000-c432eeabf339e3f7593b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000t-9034000000-4fd3316b534c1c9695e5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00m0-4191000000-c1b630ac82bbe1ed3eec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-8590000000-1aec7778a60c3c83b96f	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2093.0 Log mg/kg [1200:3700]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000385	Antiprotozoals?Antiprotozoals are synthetic chemicals designed to target and eliminate protozoan infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	Not Available

Pathways

2 pathwaysPathway Source: PathBank

Artesunate Action Pathway

Artesunate Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	PCNA-associated factor	Q15004	Humans	Predicted (SEA)	Prediction Confidence Score 0.388 Applicability Domain 0.388 Statistical Significance 8.00e-05 Supporting Reference Compounds 1 E-value 0.622794
Click to view 3D structure	Krueppel-like factor 5	Q13887	Humans	Predicted (SEA)	Prediction Confidence Score 0.233 Applicability Domain 0.635 Statistical Significance 0.0364 Supporting Reference Compounds 42 E-value 283.371
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.467 Statistical Significance 0.7772 Supporting Reference Compounds 1538 E-value 6050.13
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	Prediction Confidence Score 0.227 Applicability Domain 0.467 Statistical Significance 0.635 Supporting Reference Compounds 793 E-value 4943.58
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	Prediction Confidence Score 0.223 Applicability Domain 0.239 Low confidence Statistical Significance 0.1447 Supporting Reference Compounds 197 E-value 1126.48
Click to view 3D structure	Zinc finger protein GLI1	P47806	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.221 Applicability Domain 0.635 Statistical Significance 0.0354 Supporting Reference Compounds 35 E-value 275.275
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	Prediction Confidence Score 0.218 Applicability Domain 0.234 Low confidence Statistical Significance 0.05 Supporting Reference Compounds 54 E-value 389.635
Click to view 3D structure	Protein Wnt-3a	P27467	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.218 Applicability Domain 0.635 Statistical Significance 0.043 Supporting Reference Compounds 31 E-value 334.518
Click to view 3D structure	Bile acid receptor	Q96RI1	Humans	Predicted (SEA)	Prediction Confidence Score 0.202 Applicability Domain 0.234 Low confidence Statistical Significance 0.2929 Supporting Reference Compounds 94 E-value 2280.52
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	Prediction Confidence Score 0.201 Applicability Domain 0.467 Statistical Significance 0.4068 Supporting Reference Compounds 150 E-value 3167.3
Click to view 3D structure	Potassium-transporting ATPase alpha chain 2	P54707	Humans	Predicted (SEA)	Prediction Confidence Score 0.192 Applicability Domain 0.207 Low confidence Statistical Significance 0.002 Supporting Reference Compounds 2 E-value 15.8812
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 2	P17706	Humans	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.239 Low confidence Statistical Significance 0.2496 Supporting Reference Compounds 60 E-value 1943.12
Click to view 3D structure	CMP-N-acetylneuraminate-beta-galactosamide-alpha-2,3-sialyltransferase 2	Q11205	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.186 Applicability Domain 0.186 Low confidence Statistical Significance 0.0063 Supporting Reference Compounds 1 E-value 49.1229
Click to view 3D structure	Lysine-specific demethylase 2A	Q9Y2K7	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.228 Low confidence Statistical Significance 0.2151 Supporting Reference Compounds 35 E-value 1674.54
Click to view 3D structure	Histone lysine demethylase PHF8	Q9UPP1	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.228 Low confidence Statistical Significance 0.0287 Supporting Reference Compounds 14 E-value 223.116
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.231 Low confidence Statistical Significance 0.5685 Supporting Reference Compounds 104 E-value 4425.42
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.183 Applicability Domain 0.21 Low confidence Statistical Significance 0.1413 Supporting Reference Compounds 73 E-value 1100.09
Click to view 3D structure	Neurogenic locus notch homolog protein 1	Q01705	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.179 Low confidence Statistical Significance 0.0029 Supporting Reference Compounds 1 E-value 22.4206
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	Prediction Confidence Score 0.179 Applicability Domain 0.21 Low confidence Statistical Significance 0.6354 Supporting Reference Compounds 146 E-value 4946.38
Click to view 3D structure	11-beta-hydroxysteroid dehydrogenase 1	P28845	Humans	Predicted (SEA)	Prediction Confidence Score 0.178 Applicability Domain 0.231 Low confidence Statistical Significance 0.4428 Supporting Reference Compounds 76 E-value 3447.16
Click to view 3D structure	Vitamin D3 receptor	P11473	Humans	Predicted (SEA)	Prediction Confidence Score 0.177 Applicability Domain 0.25 Low confidence Statistical Significance 0.3488 Supporting Reference Compounds 41 E-value 2715.38
Click to view 3D structure	Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	Humans	Predicted (SEA)	Prediction Confidence Score 0.177 Applicability Domain 0.21 Low confidence Statistical Significance 0.2829 Supporting Reference Compounds 69 E-value 2202.2
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.177 Applicability Domain 0.21 Low confidence Statistical Significance 0.0752 Supporting Reference Compounds 19 E-value 585.193
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-1	P50997	Canis lupus familiaris	Predicted (SEA)	Prediction Confidence Score 0.176 Applicability Domain 0.202 Low confidence Statistical Significance 0.0019 Supporting Reference Compounds 4 E-value 14.7914
Click to view 3D structure	11-beta-hydroxysteroid dehydrogenase type 2	P80365	Humans	Predicted (SEA)	Prediction Confidence Score 0.175 Applicability Domain 0.231 Low confidence Statistical Significance 0.1311 Supporting Reference Compounds 32 E-value 1020.37