Quinghaosu reduced succinate ester

Details

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Internal ID 4dc871c4-4a81-4f0f-b33e-0012426af4bf
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Artemisinins
IUPAC Name 4-oxo-4-[[(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-yl]oxy]butanoic acid
SMILES (Canonical) CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC(=O)CCC(=O)O)C
SMILES (Isomeric) C[C@@H]1CC[C@H]2[C@H]([C@@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)OC(=O)CCC(=O)O)C
InChI InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18?,19-/m1/s1
InChI Key FIHJKUPKCHIPAT-RLQWWVEOSA-N
Popularity 2,076 references in papers

Physical and Chemical Properties

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Molecular Formula C19H28O8
Molecular Weight 384.40 g/mol
Exact Mass 384.17841785 g/mol
Topological Polar Surface Area (TPSA) 101.00 Ų
XlogP 2.50
Atomic LogP (AlogP) 2.60
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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Arsumax (TN)
Artesunate (USAN)
Artesunate [USAN]
88495-63-0
Artesunate [USAN:INN]
Artesunatum [INN-Latin]
Succinyl dihydroartemisinin
Artesunato [INN-Spanish]
Artesunate (superseded RN)
Quinghaosu reduced succinate ester
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Quinghaosu reduced succinate ester

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9364 93.64%
Caco-2 - 0.5620 56.20%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability + 0.6571 65.71%
Subcellular localzation Mitochondria 0.6655 66.55%
OATP2B1 inhibitior - 0.7162 71.62%
OATP1B1 inhibitior + 0.8573 85.73%
OATP1B3 inhibitior + 0.8479 84.79%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.6061 60.61%
P-glycoprotein inhibitior - 0.5668 56.68%
P-glycoprotein substrate - 0.8747 87.47%
CYP3A4 substrate + 0.7117 71.17%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8709 87.09%
CYP3A4 inhibition - 0.7973 79.73%
CYP2C9 inhibition - 0.9272 92.72%
CYP2C19 inhibition - 0.9155 91.55%
CYP2D6 inhibition - 0.9658 96.58%
CYP1A2 inhibition - 0.6802 68.02%
CYP2C8 inhibition + 0.5923 59.23%
CYP inhibitory promiscuity - 0.9911 99.11%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.7079 70.79%
Eye corrosion - 0.9886 98.86%
Eye irritation - 0.9541 95.41%
Skin irritation - 0.6016 60.16%
Skin corrosion - 0.8883 88.83%
Ames mutagenesis - 0.6854 68.54%
Human Ether-a-go-go-Related Gene inhibition - 0.7546 75.46%
Micronuclear - 0.8600 86.00%
Hepatotoxicity + 0.9440 94.40%
skin sensitisation - 0.8842 88.42%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity - 0.8220 82.20%
Acute Oral Toxicity (c) IV 0.3752 37.52%
Estrogen receptor binding + 0.8906 89.06%
Androgen receptor binding + 0.8697 86.97%
Thyroid receptor binding + 0.7062 70.62%
Glucocorticoid receptor binding + 0.8970 89.70%
Aromatase binding + 0.7057 70.57%
PPAR gamma + 0.8132 81.32%
Honey bee toxicity - 0.8345 83.45%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9417 94.17%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.61% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.32% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.28% 94.45%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 91.48% 96.38%
CHEMBL340 P08684 Cytochrome P450 3A4 90.58% 91.19%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.23% 97.25%
CHEMBL5255 O00206 Toll-like receptor 4 88.92% 92.50%
CHEMBL4040 P28482 MAP kinase ERK2 87.84% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.34% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.17% 85.14%
CHEMBL221 P23219 Cyclooxygenase-1 84.81% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.71% 97.09%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.67% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.10% 95.50%
CHEMBL5028 O14672 ADAM10 81.04% 97.50%

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 annua
Artemisia carvifolia

Cross-Links

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PubChem 16394563
NPASS NPC169150