[(2R,3R,4S,5R,6S)-6-[[(3aR,5aS,8R,8aR,9aR)-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl]oxy]-4-acetyloxy-3,5-dihydroxyoxan-2-yl]methyl acetate

Details

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Internal ID 5382b25b-1ae7-46a9-9fda-efa8a21b12f2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(2R,3R,4S,5R,6S)-6-[[(3aR,5aS,8R,8aR,9aR)-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl]oxy]-4-acetyloxy-3,5-dihydroxyoxan-2-yl]methyl acetate
SMILES (Canonical) CC(=O)OCC1C(C(C(C(O1)OC2(CCC3C2CC4C(CC3=C)OC(=O)C4=C)C)O)OC(=O)C)O
SMILES (Isomeric) CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@]2(CC[C@H]3[C@H]2C[C@H]4[C@@H](CC3=C)OC(=O)C4=C)C)O)OC(=O)C)O
InChI InChI=1S/C25H34O10/c1-11-8-18-16(12(2)23(30)33-18)9-17-15(11)6-7-25(17,5)35-24-21(29)22(32-14(4)27)20(28)19(34-24)10-31-13(3)26/h15-22,24,28-29H,1-2,6-10H2,3-5H3/t15-,16-,17-,18-,19-,20-,21-,22+,24+,25-/m1/s1
InChI Key SWLAMBRETNNVQF-KUMDYOAKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C25H34O10
Molecular Weight 494.50 g/mol
Exact Mass 494.21519728 g/mol
Topological Polar Surface Area (TPSA) 138.00 Ų
XlogP 0.80
Atomic LogP (AlogP) 1.18
H-Bond Acceptor 10
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3R,4S,5R,6S)-6-[[(3aR,5aS,8R,8aR,9aR)-8-methyl-1,5-dimethylidene-2-oxo-3a,4,5a,6,7,8a,9,9a-octahydroazuleno[6,7-b]furan-8-yl]oxy]-4-acetyloxy-3,5-dihydroxyoxan-2-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9262 92.62%
Caco-2 - 0.8069 80.69%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.7906 79.06%
OATP2B1 inhibitior - 0.8617 86.17%
OATP1B1 inhibitior + 0.7915 79.15%
OATP1B3 inhibitior + 0.9116 91.16%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7636 76.36%
BSEP inhibitior - 0.6026 60.26%
P-glycoprotein inhibitior - 0.4413 44.13%
P-glycoprotein substrate - 0.6692 66.92%
CYP3A4 substrate + 0.7170 71.70%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8994 89.94%
CYP3A4 inhibition - 0.8497 84.97%
CYP2C9 inhibition - 0.7897 78.97%
CYP2C19 inhibition - 0.9000 90.00%
CYP2D6 inhibition - 0.9515 95.15%
CYP1A2 inhibition - 0.8086 80.86%
CYP2C8 inhibition + 0.5225 52.25%
CYP inhibitory promiscuity - 0.9170 91.70%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6481 64.81%
Eye corrosion - 0.9873 98.73%
Eye irritation - 0.9240 92.40%
Skin irritation - 0.5438 54.38%
Skin corrosion - 0.9262 92.62%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4482 44.82%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.5750 57.50%
skin sensitisation - 0.8853 88.53%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.7556 75.56%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity + 0.4559 45.59%
Acute Oral Toxicity (c) III 0.3989 39.89%
Estrogen receptor binding + 0.6646 66.46%
Androgen receptor binding + 0.6979 69.79%
Thyroid receptor binding - 0.5526 55.26%
Glucocorticoid receptor binding + 0.6703 67.03%
Aromatase binding + 0.6524 65.24%
PPAR gamma + 0.5638 56.38%
Honey bee toxicity - 0.6532 65.32%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9857 98.57%

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 97.10% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.78% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.05% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.97% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.78% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.47% 94.45%
CHEMBL226 P30542 Adenosine A1 receptor 90.79% 95.93%
CHEMBL2996 Q05655 Protein kinase C delta 88.40% 97.79%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.23% 95.89%
CHEMBL5255 O00206 Toll-like receptor 4 87.90% 92.50%
CHEMBL340 P08684 Cytochrome P450 3A4 87.22% 91.19%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.81% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.68% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.03% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.67% 95.56%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.36% 94.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.45% 99.23%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 80.95% 95.83%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.38% 94.00%
CHEMBL5957 P21589 5'-nucleotidase 80.25% 97.78%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.20% 86.33%

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.
Hymenoxys richardsonii

Cross-Links

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PubChem 101927622
LOTUS LTS0005583
wikiData Q105262737