Artesunate

Details

• Internal ID: 9e91f941-5aeb-4725-8c2d-1ac9e01bee6f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Artemisinins
• IUPAC Name: 4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoic acid
• InChI: 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-AHIGJZGOSA-N
• Popularity: 5,801 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₈
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.17841785 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• Artesunic acid
• Arsumax
• 88495-63-0
• Plasmotrin
• Qinghaozhi
• Saphnate
• Artesunato
• Artesunatum
• Dihydroqinghasu hemsuccinate
• Zysunate
• CHEBI:63918
• WR 256283
• Dihydroqinghaosu hemisuccinate
• LJPC-0118
• Dihydroartemisinine-12alpha-succinate
• 60W3249T9M
• NSC-712571
• DTXSID3042681
• Butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester
• 4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoic acid
• Butanedioic acid, mono((3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-yl) ester
• 4-oxo-4-{[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10-yl]oxy}butanoic acid
• 4-oxo-4-(((1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo(10.3.1.04,13.08,13)hexadecan-10-yl)oxy)butanoic acid
• 4-oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano(4,3-j)(1,2)benzodioxepin-10-yl)oxy)butanoic acid
• butanedioic acid, 1-((3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-yl) ester
• alpha-artesunic acid
• RefChem:54307
• Dihydroartemisinin, Succinyl
• P01BE03
• DTXCID601508461
• SM804
• Dihydroartemisinine 12 alpha succinate
• 4-oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxypyrano(4,3-j)-1,2-benzodioxepin-10-yl)oxy)butanoic acid
• 618-170-5
• Butanedioic acid, mono((5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-yl) ester
• Arinate
• .alpha.-artesunic acid
• Succinyl dihydroartemisinin
• Arsuamoon
• Asumax
• Gsunate Forte
• Artesunata
• Plasmotrim
• Cosinate
• C19H28O8
• Artesunate [USAN]
• (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10-ol, hydrogen succinate
• Artesunate [INN]
• Armax 200
• Artesunatum [INN-Latin]
• Artesunato [INN-Spanish]
• Artsuna
• Nuartez
• Artesunate [USAN:INN:BAN]
• MFCD00866204
• UNII-60W3249T9M
• HSDB 7458
• Quinghaosu reduced succinate ester
• D95
• WR-256283
• Artesunate (Standard)
• ARTESUNATE [MI]
• ARTESUNATE [HSDB]
• ARTESUNATE [VANDF]
• ARTESUNATE [MART.]
• ARTESUNATE [USP-RS]
• ARTESUNATE [WHO-DD]
• ARTESUNATE [WHO-IP]
• MLS006011590
• CHEMBL361497
• GTPL9956
• orb1310621
• ARTESUNATE [ORANGE BOOK]
• SCHEMBL14552891
• HY-N0193R
• FIHJKUPKCHIPAT-AHIGJZGOSA-N
• ARTESUNATUM [WHO-IP LATIN]
• HY-N0193
• STR09744
• BDBM50248021
• AKOS037515734
• CS-8151
• DB09274
• FA17994
• NCGC00164600-10
• NCGC00164600-15
• 4-oxo-4-(((3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)butanoic acid
• SMR002499399
• NS00099352
• DIHYDROARTEMISININE-12.ALPHA.-SUCCINATE
• EN300-6482026
• Q707939
• BRD-K54634444-001-05-9
• WR-256283;ART;Armax 200;SM-804;HSDB-7458
• 3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE
• 4-OXO-4-(3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXYPYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE
• 4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0?,(1)(3).0?,(1)(3)]hexadecan-10-yl]oxy}butanoic acid
• 4-oxo-4-{[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-yl]oxy}butanoic acid
• Butanedioic acid mono(3R,5?S,6R,8?S,9R,10S,12R,12?R)-decahydro-3,6 ,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester;Artesunic acid
• BUTANEDIOIC ACID, MONO(DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL) ESTER, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.ALPHA.,10.BETA.,12.BETA.,12AR*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9364	93.64%
Caco-2	-	0.5620	56.20%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6655	66.55%
OATP2B1 inhibitior	-	0.7162	71.62%
OATP1B1 inhibitior	+	0.8573	85.73%
OATP1B3 inhibitior	+	0.8479	84.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6061	60.61%
P-glycoprotein inhibitior	-	0.5668	56.68%
P-glycoprotein substrate	-	0.8747	87.47%
CYP3A4 substrate	+	0.7117	71.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8709	87.09%
CYP3A4 inhibition	-	0.7973	79.73%
CYP2C9 inhibition	-	0.9272	92.72%
CYP2C19 inhibition	-	0.9155	91.55%
CYP2D6 inhibition	-	0.9658	96.58%
CYP1A2 inhibition	-	0.6802	68.02%
CYP2C8 inhibition	+	0.5923	59.23%
CYP inhibitory promiscuity	-	0.9911	99.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7079	70.79%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6016	60.16%
Skin corrosion	-	0.8883	88.83%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7546	75.46%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.9440	94.40%
skin sensitisation	-	0.8842	88.42%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8220	82.20%
Acute Oral Toxicity (c)	IV	0.3752	37.52%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.7062	70.62%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	+	0.7057	70.57%
PPAR gamma	+	0.8132	81.32%
Honey bee toxicity	-	0.8345	83.45%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9417	94.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.61%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.32%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.28%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.48%	96.38%
CHEMBL340	P08684	Cytochrome P450 3A4	90.58%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.23%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	88.92%	92.50%
CHEMBL4040	P28482	MAP kinase ERK2	87.84%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.34%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.17%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	84.81%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.71%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.67%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.10%	95.50%
CHEMBL5028	O14672	ADAM10	81.04%	97.50%

Plants that contains it

• Artemisia annua
• Artemisia carvifolia

Cross-Links

• PubChem: 6917864
• NPASS: NPC30102
• ChEMBL: CHEMBL361497