Artenimol

Details

• Internal ID: ab72f901-e01a-41e0-8ea8-04dcb239bce3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Artemisinins
• IUPAC Name: (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-ol
• InChI: InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
• InChI Key: BJDCWCLMFKKGEE-ISOSDAIHSA-N
• Popularity: 1,710 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₅
• Molecular Weight: 284.35 g/mol
• Exact Mass: 284.16237386 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.19
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Artenimol
• Alaxin
• Dihydroqinghaosu
• Cotecxin
• Dihydroartemisinine
• Santecxin
• Salaxin
• Di-hydroqinghaosu
• Dynamax
• GNF-PF-5634
• beta-Dihydroartemisinin
• 6A9O50735X
• Dihydroquinghaosu
• EURARTESIM COMPONENT DIHYDROARTEMISININ
• Artenimolum
• (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-ol
• (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
• quinghaosu, dihydro-
• artemisinin, dihydro-
• (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-ol
• (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
• (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
• I2-dihydroartemisinine
• RefChem:114268
• DIHYDROARTEMISININ, BETA-
• P01BE05
• (1S,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-ol
• dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12aR*))-
• (1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo(10.3.1.04,13.08,13)hexadecan-10-ol
• Dihydroartemisinin
• 71939-50-9
• 81496-82-4
• Dihydro Artemisinin
• Artenimol [INN]
• DHQHS 2
• .beta.-dihydroartemisinin
• Dihydroartemisinin, .beta.-
• 3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol, decahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10S,12R,12aR)-
• CHEMBL307261
• MFCD00274495
• ARTENIMOL [USAN]
• ARTENIMOL [MART.]
• ARTENIMOL [WHO-DD]
• ARTENIMOL [WHO-IP]
• DIHYDROARTEMISININ [MI]
• GTPL9957
• orb1310451
• SCHEMBL17156483
• BJDCWCLMFKKGEE-ISOSDAIHSA-N
• CHEBI:135921
• DTXSID501021652
• GLXC-07598
• ARTENIMOLUM [WHO-IP LATIN]
• DIHYDROARTEMISININ [USP-RS]
• DIHYDROARTEMISININ [WHO-DD]
• HY-N0176
• MSK163132
• AKOS032949625
• CS-5595
• FD11674
• SY058680
• NS00071253
• A11600
• EN300-7419972
• Dihydroartemisinin,mixture of alpha and beta isomers
• BRD-K62213621-001-01-6
• (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-ol
• (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-ol;?-Dihydroartemisinin ;Alaxin
• (3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-ol
• (3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8606	86.06%
Caco-2	+	0.7844	78.44%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4694	46.94%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.9063	90.63%
OATP1B3 inhibitior	+	0.9288	92.88%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8689	86.89%
P-glycoprotein inhibitior	-	0.8854	88.54%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	+	0.6955	69.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7967	79.67%
CYP3A4 inhibition	-	0.9422	94.22%
CYP2C9 inhibition	-	0.9321	93.21%
CYP2C19 inhibition	-	0.8954	89.54%
CYP2D6 inhibition	-	0.9603	96.03%
CYP1A2 inhibition	+	0.7434	74.34%
CYP2C8 inhibition	+	0.4751	47.51%
CYP inhibitory promiscuity	-	0.9857	98.57%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6461	64.61%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9571	95.71%
Skin irritation	-	0.5969	59.69%
Skin corrosion	-	0.8729	87.29%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6926	69.26%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8583	85.83%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6556	65.56%
Acute Oral Toxicity (c)	III	0.4275	42.75%
Estrogen receptor binding	-	0.5169	51.69%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.7901	79.01%
Glucocorticoid receptor binding	+	0.5674	56.74%
Aromatase binding	+	0.5526	55.26%
PPAR gamma	+	0.7979	79.79%
Honey bee toxicity	-	0.8637	86.37%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.8964	89.64%

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	96.13%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.59%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.30%	96.38%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.79%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	88.25%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.98%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.36%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.85%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.19%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.35%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.32%	94.45%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	82.02%	97.31%
CHEMBL1871	P10275	Androgen Receptor	81.69%	96.43%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.85%	96.77%

Plants that contains it

• Artemisia annua
• Artemisia carvifolia

Cross-Links

• PubChem: 3000518
• NPASS: NPC53868
• ChEMBL: CHEMBL307261