Artemether

Details

• Internal ID: 6778dc29-4c06-435f-b4a7-729a182f2e78
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Artemisinins
• IUPAC Name: (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• SMILES (Canonical): CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC)C
• InChI: InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1
• InChI Key: SXYIRMFQILZOAM-HVNFFKDJSA-N
• Popularity: 3,403 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₅
• Molecular Weight: 298.37 g/mol
• Exact Mass: 298.17802393 g/mol
• Topological Polar Surface Area (TPSA): 46.20 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 71963-77-4
• beta-Artemether
• Dihydroartemisinin methyl ether
• Artemetero
• Artemetherum
• Artesaph
• Falcidol
• Malartem
• Paluther
• Gvither
• Methyl-dihydroartemisinine
• Artemisininelactol methyl ether
• Artemetheri
• Larither
• beta-Dihydroartemisinin methyl ether
• SM 224
• Dihydroqinghaosu methyl ether
• CHEBI:195280
• DTXSID7040651
• C7D6T3H22J
• DTXCID30819889
• SM224
• (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• O-Methyldihydroartemisinine
• (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane
• NSC-665970
• NSC-759820
• 10-methoxy-1,5,9-trimethyl-(1R,4S,5R,8S,9R,10S,12R,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• beta Arthemeter
• COARTEM COMPONENT ARTEMETHER
• alpha Artemether
• (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo(10.3.1.0^(4,13).0^(8,13))hexadecane
• (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo(10.3.1.04,13.08,13)hexadecane
• 10-methoxy-1,5,9-trimethyl-(1R,4S,5R,8S,9R,10S,12R,13R)-11,14,15,16-tetraoxatetracyclo(10.3.1.04,13.08,13)hexadecane
• 3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)-
• 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)-
• RefChem:560091
• O Methyldihydroartemisinine
• P01BE02
• 663-549-0
• 695-829-3
• Artenam
• C16H26O5
• Artemos
• CPD000469218
• .beta.-Artemether
• SM-224
• Artemetero [INN-Spanish]
• Artemetherum [INN-Latin]
• methoxy(trimethyl)[?]
• (3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-methoxy-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene
• Dihydroquinghaosu methyl ether
• HSDB 7456
• NSC 665970
• UNII-C7D6T3H22J
• Artimist
• Qinghao
• beta artemether
• Artemether [USAN:INN:BAN]
• NSC665970
• NCGC00164591-01
• (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin
• Dihydroartemisinin impurity g
• MLS001424249
• Artemether (JAN/USAN/INN)
• CHEMBL566534
• GTPL9955
• orb1308984
• SCHEMBL1650501
• Artemether, >=98% (HPLC)
• GLXC-03969
• HMS2052L09
• HMS2232J21
• HY-N0402
• Tox21_112217
• BDBM50248200
• AKOS026750084
• CCG-101180
• DB06697
• FA17991
• NC00430
• NCGC00164591-11
• 3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-, (3-alpha,5a-beta,6-beta,8a-beta,9-alpha,12-beta,12aR)-, (+)-
• Artemether 100 microg/mL in Acetonitrile
• SMR000469218
• CAS-71963-77-4
• NS00001253
• D02483
• EN300-122380
• AB00698368-05
• AB00698368_06
• Q416199
• BRD-K39621635-001-05-5
• Z1541759910
• Artemether, United States Pharmacopeia (USP) Reference Standard
• (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0;{4,13}.0;{8,13}]hexadecane
• (3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-methoxy-3,6,9-trimethyldecahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepine
• (3r,5as,6r,8as,9r,10s,12r,12ar)-decahydro-10methoxy-3,6,9-trimethyl-3,12-epoxy-12h-pyrano[4,3-j]-1,2benzodioxepin
• D8Z

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9394	93.94%
Caco-2	+	0.8599	85.99%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.4368	43.68%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.9120	91.20%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8893	88.93%
P-glycoprotein inhibitior	-	0.7903	79.03%
P-glycoprotein substrate	-	0.9162	91.62%
CYP3A4 substrate	+	0.7144	71.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7704	77.04%
CYP3A4 inhibition	-	0.9434	94.34%
CYP2C9 inhibition	-	0.9413	94.13%
CYP2C19 inhibition	-	0.8733	87.33%
CYP2D6 inhibition	-	0.9474	94.74%
CYP1A2 inhibition	+	0.6829	68.29%
CYP2C8 inhibition	+	0.5890	58.90%
CYP inhibitory promiscuity	-	0.9672	96.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6560	65.60%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9015	90.15%
Skin irritation	-	0.7066	70.66%
Skin corrosion	-	0.9210	92.10%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6016	60.16%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5177	51.77%
skin sensitisation	-	0.8649	86.49%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.5992	59.92%
Acute Oral Toxicity (c)	IV	0.4732	47.32%
Estrogen receptor binding	+	0.6854	68.54%
Androgen receptor binding	+	0.8536	85.36%
Thyroid receptor binding	+	0.8462	84.62%
Glucocorticoid receptor binding	+	0.5930	59.30%
Aromatase binding	+	0.5465	54.65%
PPAR gamma	+	0.7843	78.43%
Honey bee toxicity	-	0.7423	74.23%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.8648	86.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	562.3 nM; 562.3 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.36%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.28%	97.25%
CHEMBL240	Q12809	HERG	89.12%	89.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.60%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.31%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.87%	97.14%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	86.53%	97.31%
CHEMBL2243	O00519	Anandamide amidohydrolase	86.26%	97.53%
CHEMBL1871	P10275	Androgen Receptor	86.03%	96.43%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.80%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.77%	94.45%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	83.80%	98.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.06%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.75%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.18%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.17%	94.80%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.87%	91.03%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.01%	96.38%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	80.96%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	80.07%	92.50%

Plants that contains it

• Artemisia annua
• Artemisia carvifolia

Cross-Links

• PubChem: 68911
• NPASS: NPC51956
• ChEMBL: CHEMBL566534