Dihydroartemisinate

Details

• Internal ID: 9947b46f-6e29-4ac9-8d37-10275d5bbd9b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoate
• SMILES (Canonical): CC1CCC(C2C1CCC(=C2)C)C(C)C(=O)[O-]
• SMILES (Isomeric): C[C@@H]1CC[C@H]([C@@H]2[C@H]1CCC(=C2)C)[C@@H](C)C(=O)[O-]
• InChI: InChI=1S/C15H24O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10-14H,4-7H2,1-3H3,(H,16,17)/p-1/t10-,11-,12+,13+,14+/m1/s1
• InChI Key: JYGAZEJXUVDYHI-DGTMBMJNSA-M
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃O₂-
• Molecular Weight: 235.34 g/mol
• Exact Mass: 235.169804972 g/mol
• Topological Polar Surface Area (TPSA): 40.10 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• CHEBI:143905
• RefChem:1083596
• (2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoate
• (11R)-dihydroartemisinate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.8751	87.51%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Plasma membrane	0.5859	58.59%
OATP2B1 inhibitior	-	0.8501	85.01%
OATP1B1 inhibitior	+	0.9158	91.58%
OATP1B3 inhibitior	+	0.8891	88.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.9087	90.87%
P-glycoprotein inhibitior	-	0.9427	94.27%
P-glycoprotein substrate	-	0.7971	79.71%
CYP3A4 substrate	+	0.5098	50.98%
CYP2C9 substrate	+	0.6230	62.30%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.8861	88.61%
CYP2C9 inhibition	-	0.7614	76.14%
CYP2C19 inhibition	-	0.5912	59.12%
CYP2D6 inhibition	-	0.9151	91.51%
CYP1A2 inhibition	-	0.6883	68.83%
CYP2C8 inhibition	-	0.8477	84.77%
CYP inhibitory promiscuity	-	0.7879	78.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.5866	58.66%
Eye corrosion	-	0.9101	91.01%
Eye irritation	-	0.7276	72.76%
Skin irritation	-	0.6291	62.91%
Skin corrosion	-	0.9764	97.64%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6227	62.27%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.5500	55.00%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7742	77.42%
Acute Oral Toxicity (c)	III	0.8388	83.88%
Estrogen receptor binding	-	0.8405	84.05%
Androgen receptor binding	+	0.5944	59.44%
Thyroid receptor binding	-	0.6422	64.22%
Glucocorticoid receptor binding	-	0.6446	64.46%
Aromatase binding	-	0.8581	85.81%
PPAR gamma	-	0.7837	78.37%
Honey bee toxicity	-	0.9327	93.27%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	94.91%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.10%	94.80%
CHEMBL4040	P28482	MAP kinase ERK2	93.00%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.75%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.67%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.00%	93.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.57%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.40%	96.47%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.35%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.13%	95.89%

Plants that contains it

• Artemisia annua
• Artemisia carvifolia

Cross-Links

• PubChem: 25245484
• NPASS: NPC158548