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[(3aS,6aR,7R,8R,9R,9aR,9bR)-8-acetyloxy-7-hydroxy-3,6-dimethylidene-2-oxo-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[8,7-b]furan-9-yl]methyl 3-methylbutanoate

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 bc08697e-9c3d-4933-be83-3e4741934acb
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aS,6aR,7R,8R,9R,9aR,9bR)-8-acetyloxy-7-hydroxy-3,6-dimethylidene-2-oxo-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[8,7-b]furan-9-yl]methyl 3-methylbutanoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C22H30O7/c1-10(2)8-16(24)27-9-15-18-17(19(25)21(15)28-13(5)23)11(3)6-7-14-12(4)22(26)29-20(14)18/h10,14-15,17-21,25H,3-4,6-9H2,1-2,5H3/t14-,15-,17-,18-,19+,20-,21+/m0/s1
InChI Key DYDVEDXRKBHWQE-MOEGVCJQSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C22H30O7
Molecular Weight 406.50 g/mol
Exact Mass 406.19915329 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 2.30
Atomic LogP (AlogP) 2.18
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,6aR,7R,8R,9R,9aR,9bR)-8-acetyloxy-7-hydroxy-3,6-dimethylidene-2-oxo-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[8,7-b]furan-9-yl]methyl 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 + 0.9496 94.96%
Caco-2 - 0.6826 68.26%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7608 76.08%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8472 84.72%
OATP1B3 inhibitior + 0.9241 92.41%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior - 0.6126 61.26%
P-glycoprotein inhibitior - 0.5911 59.11%
P-glycoprotein substrate - 0.6778 67.78%
CYP3A4 substrate + 0.6404 64.04%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8823 88.23%
CYP3A4 inhibition - 0.7585 75.85%
CYP2C9 inhibition - 0.6590 65.90%
CYP2C19 inhibition - 0.7278 72.78%
CYP2D6 inhibition - 0.9021 90.21%
CYP1A2 inhibition - 0.5745 57.45%
CYP2C8 inhibition - 0.7059 70.59%
CYP inhibitory promiscuity - 0.8616 86.16%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8943 89.43%
Carcinogenicity (trinary) Non-required 0.6001 60.01%
Eye corrosion - 0.9622 96.22%
Eye irritation - 0.7648 76.48%
Skin irritation - 0.6546 65.46%
Skin corrosion - 0.9298 92.98%
Ames mutagenesis - 0.6670 66.70%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear - 0.8600 86.00%
Hepatotoxicity + 0.5750 57.50%
skin sensitisation - 0.7945 79.45%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.5889 58.89%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity + 0.4915 49.15%
Acute Oral Toxicity (c) III 0.4907 49.07%
Estrogen receptor binding + 0.6869 68.69%
Androgen receptor binding + 0.5301 53.01%
Thyroid receptor binding - 0.5288 52.88%
Glucocorticoid receptor binding + 0.6665 66.65%
Aromatase binding - 0.5635 56.35%
PPAR gamma + 0.5648 56.48%
Honey bee toxicity - 0.7912 79.12%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9722 97.22%

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 95.96% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.10% 94.45%
CHEMBL226 P30542 Adenosine A1 receptor 91.08% 95.93%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.84% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.41% 97.09%
CHEMBL2581 P07339 Cathepsin D 89.23% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.39% 97.25%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.02% 85.14%
CHEMBL340 P08684 Cytochrome P450 3A4 87.63% 91.19%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.53% 95.89%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.70% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.91% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.56% 99.23%
CHEMBL221 P23219 Cyclooxygenase-1 84.06% 90.17%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.47% 99.17%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 82.65% 94.80%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.42% 94.33%
CHEMBL5103 Q969S8 Histone deacetylase 10 82.31% 90.08%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.30% 95.56%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 82.19% 96.47%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.78% 93.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.40% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 80.01% 92.50%

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.
Echinops spinosissimus subsp. neumayeri

Cross-Links

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PubChem 12151102
LOTUS LTS0249869
wikiData Q104991331