Artemisin

Details

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Internal ID 658943c0-d2ce-4b79-b56b-34a26372a40c
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name (3S,3aR,4S,5aS,9bS)-4-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
SMILES (Canonical) CC1C2C(CC3(C=CC(=O)C(=C3C2OC1=O)C)C)O
SMILES (Isomeric) C[C@H]1[C@@H]2[C@H](C[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C)O
InChI InChI=1S/C15H18O4/c1-7-9(16)4-5-15(3)6-10(17)11-8(2)14(18)19-13(11)12(7)15/h4-5,8,10-11,13,17H,6H2,1-3H3/t8-,10-,11+,13-,15+/m0/s1
InChI Key LUHMMHZLDLBAKX-DBIGVJDZSA-N
Popularity 85 references in papers

Physical and Chemical Properties

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Molecular Formula C15H18O4
Molecular Weight 262.30 g/mol
Exact Mass 262.12050905 g/mol
Topological Polar Surface Area (TPSA) 63.60 Ų
XlogP 1.10
Atomic LogP (AlogP) 1.39
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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481-05-0
Y1R67R7XWU
CHEBI:2852
(3S,3aR,4S,5aS,9bS)-4-hydroxy-3,5a,9-trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
UNII-Y1R67R7XWU
ARTEMISIN [MI]
SCHEMBL83537
CHEMBL158124
4-HYDROXYSANTONIN [MI]
DTXSID80877833
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Artemisin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9937 99.37%
Caco-2 + 0.5564 55.64%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability + 0.6571 65.71%
Subcellular localzation Mitochondria 0.6122 61.22%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9178 91.78%
OATP1B3 inhibitior + 0.9558 95.58%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.7186 71.86%
P-glycoprotein inhibitior - 0.8990 89.90%
P-glycoprotein substrate - 0.8361 83.61%
CYP3A4 substrate + 0.5854 58.54%
CYP2C9 substrate - 0.8218 82.18%
CYP2D6 substrate - 0.9032 90.32%
CYP3A4 inhibition - 0.7721 77.21%
CYP2C9 inhibition - 0.8946 89.46%
CYP2C19 inhibition - 0.9611 96.11%
CYP2D6 inhibition - 0.9696 96.96%
CYP1A2 inhibition - 0.8014 80.14%
CYP2C8 inhibition - 0.9472 94.72%
CYP inhibitory promiscuity - 0.9023 90.23%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Danger 0.4538 45.38%
Eye corrosion - 0.9835 98.35%
Eye irritation - 0.9164 91.64%
Skin irritation + 0.5624 56.24%
Skin corrosion - 0.8746 87.46%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7259 72.59%
Micronuclear - 0.5400 54.00%
Hepatotoxicity + 0.6870 68.70%
skin sensitisation - 0.6779 67.79%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity + 0.5556 55.56%
Acute Oral Toxicity (c) III 0.3951 39.51%
Estrogen receptor binding - 0.6474 64.74%
Androgen receptor binding - 0.5447 54.47%
Thyroid receptor binding - 0.6419 64.19%
Glucocorticoid receptor binding - 0.7682 76.82%
Aromatase binding - 0.8794 87.94%
PPAR gamma - 0.5593 55.93%
Honey bee toxicity - 0.9101 91.01%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9560 95.60%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.24% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.27% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 90.37% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.40% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.56% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.70% 96.09%
CHEMBL1951 P21397 Monoamine oxidase A 85.43% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.94% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.77% 100.00%
CHEMBL2581 P07339 Cathepsin D 83.13% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.52% 97.09%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Artemisia campestris subsp. campestris
Seriphidium ifranensis
Vitex agnus-castus

Cross-Links

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PubChem 65030
LOTUS LTS0008665
wikiData Q27105849