[(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R)-2-hydroxy-3-methylbutanoate

Details

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Internal ID a9efe8e8-518f-4b7a-912a-76480ab493a6
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R)-2-hydroxy-3-methylbutanoate
SMILES (Canonical) CC(C)C(C(=O)OC1CC(=C)C2CC(C(=C)C2C3C1C(=C)C(=O)O3)OC4C(C(C(C(O4)CO)O)O)O)O
SMILES (Isomeric) CC(C)[C@H](C(=O)O[C@@H]1CC(=C)[C@@H]2C[C@@H](C(=C)[C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChI InChI=1S/C26H36O11/c1-9(2)19(28)25(33)34-15-6-10(3)13-7-14(11(4)17(13)23-18(15)12(5)24(32)37-23)35-26-22(31)21(30)20(29)16(8-27)36-26/h9,13-23,26-31H,3-8H2,1-2H3/t13-,14-,15+,16+,17-,18+,19+,20+,21-,22+,23+,26+/m0/s1
InChI Key HLZBRVYCKXUHSB-FTTCLZOFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H36O11
Molecular Weight 524.60 g/mol
Exact Mass 524.22576196 g/mol
Topological Polar Surface Area (TPSA) 172.00 Ų
XlogP 0.00
Atomic LogP (AlogP) -0.65
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4R,6aR,8S,9aR,9bR)-3,6,9-trimethylidene-2-oxo-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2R)-2-hydroxy-3-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6360 63.60%
Caco-2 - 0.8525 85.25%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7901 79.01%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8282 82.82%
OATP1B3 inhibitior + 0.9573 95.73%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.5697 56.97%
P-glycoprotein inhibitior - 0.5682 56.82%
P-glycoprotein substrate - 0.5532 55.32%
CYP3A4 substrate + 0.6723 67.23%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8925 89.25%
CYP3A4 inhibition - 0.8353 83.53%
CYP2C9 inhibition - 0.8358 83.58%
CYP2C19 inhibition - 0.8231 82.31%
CYP2D6 inhibition - 0.9096 90.96%
CYP1A2 inhibition - 0.8778 87.78%
CYP2C8 inhibition - 0.6555 65.55%
CYP inhibitory promiscuity - 0.8491 84.91%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6992 69.92%
Eye corrosion - 0.9818 98.18%
Eye irritation - 0.9050 90.50%
Skin irritation - 0.7594 75.94%
Skin corrosion - 0.9344 93.44%
Ames mutagenesis - 0.6954 69.54%
Human Ether-a-go-go-Related Gene inhibition - 0.4769 47.69%
Micronuclear - 0.7041 70.41%
Hepatotoxicity - 0.6268 62.68%
skin sensitisation - 0.8340 83.40%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity - 0.5557 55.57%
Acute Oral Toxicity (c) III 0.5098 50.98%
Estrogen receptor binding + 0.6941 69.41%
Androgen receptor binding + 0.6314 63.14%
Thyroid receptor binding - 0.5285 52.85%
Glucocorticoid receptor binding - 0.5000 50.00%
Aromatase binding + 0.5360 53.60%
PPAR gamma + 0.5565 55.65%
Honey bee toxicity - 0.6324 63.24%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7500 75.00%
Fish aquatic toxicity + 0.9275 92.75%

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 98.76% 85.14%
CHEMBL220 P22303 Acetylcholinesterase 97.44% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.57% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 93.37% 97.25%
CHEMBL2581 P07339 Cathepsin D 93.30% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.02% 96.09%
CHEMBL2996 Q05655 Protein kinase C delta 92.73% 97.79%
CHEMBL221 P23219 Cyclooxygenase-1 89.63% 90.17%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 87.47% 96.47%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.44% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.49% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.04% 94.45%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.73% 90.08%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 81.53% 95.83%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.51% 99.23%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 80.11% 82.50%
CHEMBL299 P17252 Protein kinase C alpha 80.07% 98.03%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.06% 99.17%

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.
Ixeridium dentatum subsp. dentatum
Ixeris repens
Ixeris stolonifera

Cross-Links

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PubChem 162990147
LOTUS LTS0263164
wikiData Q105030404