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[(2R,3R,4S,5S,6R)-2-[[(3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

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 2fe20cf0-71a4-4c27-8537-21dc454242b9
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(2R,3R,4S,5S,6R)-2-[[(3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
SMILES (Canonical) C=C1CCC2C(C3C1CC(C3=C)OC4C(C(C(C(O4)CO)O)O)OC(=O)C=CC5=CC(=C(C=C5)O)O)OC(=O)C2=C
SMILES (Isomeric) C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)OC(=O)/C=C/C5=CC(=C(C=C5)O)O)OC(=O)C2=C
InChI InChI=1S/C30H34O11/c1-13-4-7-17-14(2)29(37)41-27(17)24-15(3)21(11-18(13)24)38-30-28(26(36)25(35)22(12-31)39-30)40-23(34)9-6-16-5-8-19(32)20(33)10-16/h5-6,8-10,17-18,21-22,24-28,30-33,35-36H,1-4,7,11-12H2/b9-6+/t17-,18-,21-,22+,24-,25+,26-,27-,28+,30+/m0/s1
InChI Key XVWBUEBOHVMPCG-UQBBOHFKSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H34O11
Molecular Weight 570.60 g/mol
Exact Mass 570.21011190 g/mol
Topological Polar Surface Area (TPSA) 172.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 1.49
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 [(2R,3R,4S,5S,6R)-2-[[(3aS,6aR,8S,9aR,9bS)-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-8-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7193 71.93%
Caco-2 - 0.8906 89.06%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7561 75.61%
OATP2B1 inhibitior - 0.8560 85.60%
OATP1B1 inhibitior + 0.8214 82.14%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.4832 48.32%
P-glycoprotein inhibitior - 0.4571 45.71%
P-glycoprotein substrate - 0.5508 55.08%
CYP3A4 substrate + 0.6839 68.39%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8672 86.72%
CYP3A4 inhibition - 0.7475 74.75%
CYP2C9 inhibition - 0.7631 76.31%
CYP2C19 inhibition - 0.6186 61.86%
CYP2D6 inhibition - 0.8399 83.99%
CYP1A2 inhibition - 0.6501 65.01%
CYP2C8 inhibition + 0.7079 70.79%
CYP inhibitory promiscuity - 0.7838 78.38%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6980 69.80%
Eye corrosion - 0.9846 98.46%
Eye irritation - 0.9159 91.59%
Skin irritation - 0.7787 77.87%
Skin corrosion - 0.9433 94.33%
Ames mutagenesis - 0.6453 64.53%
Human Ether-a-go-go-Related Gene inhibition + 0.6566 65.66%
Micronuclear - 0.7300 73.00%
Hepatotoxicity - 0.5875 58.75%
skin sensitisation - 0.7837 78.37%
Respiratory toxicity + 0.8222 82.22%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.9236 92.36%
Acute Oral Toxicity (c) III 0.4174 41.74%
Estrogen receptor binding + 0.7762 77.62%
Androgen receptor binding + 0.7019 70.19%
Thyroid receptor binding + 0.5294 52.94%
Glucocorticoid receptor binding + 0.5727 57.27%
Aromatase binding + 0.6657 66.57%
PPAR gamma + 0.7157 71.57%
Honey bee toxicity - 0.6464 64.64%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9862 98.62%

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 99.83% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 99.51% 91.49%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.38% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 94.96% 95.93%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.46% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.43% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.06% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.88% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.55% 99.17%
CHEMBL241 Q14432 Phosphodiesterase 3A 87.07% 92.94%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.63% 95.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.12% 100.00%
CHEMBL4208 P20618 Proteasome component C5 82.97% 90.00%
CHEMBL5255 O00206 Toll-like receptor 4 82.84% 92.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.92% 95.89%
CHEMBL3194 P02766 Transthyretin 81.82% 90.71%

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.
Ainsliaea acerifolia

Cross-Links

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PubChem 163085399
LOTUS LTS0013707
wikiData Q105343217