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Deoxyartemsinin

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 372511a7-84c8-4224-a70f-a9da958fc1a3
Taxonomy Organoheterocyclic compounds > Oxepanes
IUPAC Name (1R,4R,5S,8R,9S,12S)-12-hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo[7.4.1.05,14]tetradec-6-en-3-one
SMILES (Canonical) CC1C=CC2C(C(=O)OC3C2C1CCC(O3)(C)O)C
SMILES (Isomeric) C[C@@H]1C=C[C@@H]2[C@H](C(=O)O[C@@H]3C2[C@H]1CC[C@@](O3)(C)O)C
InChI InChI=1S/C15H22O4/c1-8-4-5-11-9(2)13(16)18-14-12(11)10(8)6-7-15(3,17)19-14/h4-5,8-12,14,17H,6-7H2,1-3H3/t8-,9-,10+,11-,12?,14+,15+/m1/s1
InChI Key ZHHCFKHSMKRNCX-CRBWWJEESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C15H22O4
Molecular Weight 266.33 g/mol
Exact Mass 266.15180918 g/mol
Topological Polar Surface Area (TPSA) 55.80 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.08
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

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W2ICF5Z2AN
Deoxyartemsinin (metabolite of artemether)
Pyrano(4,3,2-jk)(2)benzoxepin-2(3H)-one, 3a,6,6a,7,8,9,10a,10b-octahydro-9-hydroxy-3,6,9-trimethyl-, (3R,3aS,6R,6aS,9S,10aR)-
UNII-W2ICF5Z2AN
(1R,4R,5S,8R,9S,12S)-12-Hydroxy-4,8,12-trimethyl-2,13-dioxatricyclo(7.4.1.05,14)tetradec-6-en-3-one
1349802-43-2
DTXSID60993621
AKOS032948717
9-Hydroxy-3,6,9-trimethyl-3a,6,6a,7,8,9,10a,10b-octahydropyrano[4,3,2-jk][2]benzoxepin-2(3H)-one

2D Structure

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2D Structure of Deoxyartemsinin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9585 95.85%
Caco-2 + 0.7371 73.71%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability + 0.5857 58.57%
Subcellular localzation Mitochondria 0.5646 56.46%
OATP2B1 inhibitior - 0.8584 85.84%
OATP1B1 inhibitior + 0.8797 87.97%
OATP1B3 inhibitior + 0.9304 93.04%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.9389 93.89%
P-glycoprotein inhibitior - 0.9353 93.53%
P-glycoprotein substrate - 0.8614 86.14%
CYP3A4 substrate + 0.5998 59.98%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8562 85.62%
CYP3A4 inhibition - 0.7300 73.00%
CYP2C9 inhibition - 0.9613 96.13%
CYP2C19 inhibition - 0.9581 95.81%
CYP2D6 inhibition - 0.9672 96.72%
CYP1A2 inhibition - 0.7956 79.56%
CYP2C8 inhibition - 0.8954 89.54%
CYP inhibitory promiscuity - 0.9881 98.81%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5823 58.23%
Eye corrosion - 0.9854 98.54%
Eye irritation - 0.9653 96.53%
Skin irritation + 0.5182 51.82%
Skin corrosion - 0.8316 83.16%
Ames mutagenesis - 0.6340 63.40%
Human Ether-a-go-go-Related Gene inhibition - 0.5875 58.75%
Micronuclear - 0.8600 86.00%
Hepatotoxicity + 0.6074 60.74%
skin sensitisation - 0.7857 78.57%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity - 0.6699 66.99%
Acute Oral Toxicity (c) III 0.5042 50.42%
Estrogen receptor binding - 0.5000 50.00%
Androgen receptor binding - 0.5557 55.57%
Thyroid receptor binding + 0.6595 65.95%
Glucocorticoid receptor binding + 0.6703 67.03%
Aromatase binding - 0.7610 76.10%
PPAR gamma - 0.6998 69.98%
Honey bee toxicity - 0.9046 90.46%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.8225 82.25%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.67% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.56% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.29% 95.56%
CHEMBL4040 P28482 MAP kinase ERK2 88.53% 83.82%
CHEMBL253 P34972 Cannabinoid CB2 receptor 87.92% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.87% 96.09%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.13% 92.94%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.62% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.70% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.42% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.36% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.25% 99.23%

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 carvifolia

Cross-Links

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PubChem 156094
LOTUS LTS0040131
wikiData Q105375727