Artemisinin

Details

• Internal ID: 3ea25a6f-2544-4c9f-8e5a-fc6fbceb45c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• 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
• SMILES (Canonical): CC1CCC2C(C(=O)OC3C24C1CCC(O3)(OO4)C)C
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)C
• InChI: 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
• Popularity: 9,551 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33 g/mol
• Exact Mass: 282.14672380 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Qinghaosu
• 63968-64-9
• Huanghuahaosu
• Arteannuin
• Artemisinine
• Artemisine
• (+)-Artemisinin
• Artemisinina
• Artemisininum
• Qinghosu
• Quing Hau Sau
• Qing Hau SU
• Artemisinin [INN]
• quinghaosu
• Qing Hau Sau
• Qinghaosu [Chinese]
• Artemisinine [French]
• Artemisininum [Latin]
• Artemisinina [Spanish]
• NSC 369397
• CHEBI:223316
• Qing Hau Sau [Chinese]
• UNII-9RMU91N5K2
• BRN 4194670
• 9RMU91N5K2
• DTXSID2040652
• Artemef
• Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
• DTXCID40819890
• EC 700-290-5
• (+)-Arteannuin
• (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
• Artemisininum (Latin)
• ARTEMISININ (MART.)
• ARTEMISININ [MART.]
• Astemisinin
• ARTEMISININ (USP-RS)
• ARTEMISININ [USP-RS]
• Artesin
• (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecan-10-one
• (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
• (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-Trimethyloctahydro-3,12-epoxypyrano(4,3-j)(1,2)benzodioxepin-10(3H)-one
• 3,12-Epoxy-12H-pyranol(4,3-j)-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3-alpha,5a-beta,6-beta,8a-beta,9-alpha,12-beta,12aR*)-(+)-
• QHS
• GNF-Pf-5341
• qing hao su
• NSC-369397
• (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10(3H)-one
• (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one
• 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
• SMR000578089
• SR-01000802560
• artemsinin
• MFCD00081057
• NCGC00160207-01
• 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
• CAS-63968-64-9
• Qinghaosu,Artemisinine
• Spectrum_001351
• ARTEMISININ [MI]
• Prestwick0_000498
• Prestwick1_000498
• Prestwick2_000498
• Prestwick3_000498
• Spectrum2_001512
• Spectrum3_001549
• Spectrum4_000721
• Spectrum5_001098
• ARTEMISININ [INCI]
• SCHEMBL60304
• ARTEMISININ [WHO-DD]
• ARTEMISININ [WHO-IP]
• BSPBio_000395
• BSPBio_002998
• KBioGR_000982
• KBioSS_001831
• MLS001097650
• MLS001304036
• MLS002153846
• DivK1c_000656
• SPBio_001583
• SPBio_002316
• BPBio1_000435
• CHEMBL269671
• GTPL9954
• KBio1_000656
• KBio2_001831
• KBio2_004399
• KBio2_006967
• KBio3_002498
• P01BE01
• BLUAFEHZUWYNDE-NNWCWBAJSA-N
• NINDS_000656
• HMS2090I17
• HMS2096D17
• HMS2267N09
• HMS3269L13
• HMS3413P13
• HMS3677P13
• HMS3713D17
• Pharmakon1600-01503042
• BCP02096
• HY-B0094
• Tox21_111750
• ARTEMISININUM [WHO-IP LATIN]
• BDBM50088447
• HB1115
• NSC758216
• AKOS024457231
• Tox21_111750_1
• CCG-220498
• CS-1794
• DB13132
• LMPR0103190003
• NSC-758216
• IDI1_000656
• NCGC00161634-06
• (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one
• (3R,5AS,6R,8AS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxypyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
• AS-12692
• LS-64242
• S1282
• EN300-7390753
• Q426921
• SR-01000802560-2
• SR-01000802560-3
• SR-01000802560-4
• BRD-K13112821-001-08-3
• BRD-K13112821-001-17-4
• 2AB44F63-5D0F-424A-AA3F-24062F9C1CED
• (3R,5AS,6R,8AS,9R,12S,12AR)-3,6,9-TRIMETHYLOCTAHYDRO-3,12-EPOXYPYRANO(4,3-J )-1,2-BENZODIOXEPIN-10(3H)-ONE
• (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1, 2-benzodioxepin-10(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9590	95.90%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5202	52.02%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9703	97.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8913	89.13%
P-glycoprotein inhibitior	-	0.8249	82.49%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.7425	74.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8231	82.31%
CYP3A4 inhibition	-	0.9055	90.55%
CYP2C9 inhibition	-	0.9496	94.96%
CYP2C19 inhibition	-	0.9046	90.46%
CYP2D6 inhibition	-	0.9596	95.96%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.7365	73.65%
CYP inhibitory promiscuity	-	0.9850	98.50%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6607	66.07%
Eye corrosion	-	0.9839	98.39%
Eye irritation	-	0.8575	85.75%
Skin irritation	-	0.6028	60.28%
Skin corrosion	-	0.8636	86.36%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7340	73.40%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8425	84.25%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.5257	52.57%
Acute Oral Toxicity (c)	IV	0.6107	61.07%
Estrogen receptor binding	+	0.8232	82.32%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.7129	71.29%
Glucocorticoid receptor binding	+	0.6850	68.50%
Aromatase binding	+	0.5294	52.94%
PPAR gamma	+	0.6884	68.84%
Honey bee toxicity	-	0.8102	81.02%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.7400	74.00%
Fish aquatic toxicity	+	0.9420	94.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	158.5 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	354.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.31%	97.25%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.09%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.81%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.63%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.00%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.80%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.69%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.52%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.70%	97.14%
CHEMBL1937	Q92769	Histone deacetylase 2	82.51%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.02%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.69%	86.33%
CHEMBL1871	P10275	Androgen Receptor	80.85%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.45%	99.23%

Plants that contains it

• Artemisia annua
• Artemisia campestris
• Artemisia carvifolia
• Artemisia lancea
• Artemisia szowitziana
• Microliabum polymnioides
• Seriphidium herba-alba
• Seriphidium tenuisectum
• Tessaria integrifolia

Cross-Links

• PubChem: 68827
• NPASS: NPC30443
• ChEMBL: CHEMBL269671
• LOTUS: LTS0269880
• wikiData: Q426921