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[(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-9-acetyloxy-4,8-dihydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 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 cd1a5f79-3d3e-4a25-8088-a66ca922ab04
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
IUPAC Name [(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-9-acetyloxy-4,8-dihydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 3-methylbutanoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C22H32O8/c1-9(2)7-15(25)29-13-8-14(24)22(6)17(13)11(4)18(26)19-16(10(3)21(27)30-19)20(22)28-12(5)23/h9,11,13-14,16-20,24,26H,3,7-8H2,1-2,4-6H3/t11-,13-,14+,16+,17+,18+,19+,20+,22+/m0/s1
InChI Key AMXZJSUHONLORI-KLYHVEHESA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C22H32O8
Molecular Weight 424.50 g/mol
Exact Mass 424.20971797 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.37
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4R,5S,5aS,6S,8R,8aS,9R,9aS)-9-acetyloxy-4,8-dihydroxy-5,8a-dimethyl-1-methylidene-2-oxo-4,5,5a,6,7,8,9,9a-octahydro-3aH-azuleno[6,5-b]furan-6-yl] 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 + 0.9821 98.21%
Caco-2 - 0.6426 64.26%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.5464 54.64%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8399 83.99%
OATP1B3 inhibitior + 0.8195 81.95%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.8649 86.49%
P-glycoprotein inhibitior - 0.4931 49.31%
P-glycoprotein substrate + 0.5542 55.42%
CYP3A4 substrate + 0.6503 65.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8873 88.73%
CYP3A4 inhibition - 0.6199 61.99%
CYP2C9 inhibition - 0.7619 76.19%
CYP2C19 inhibition - 0.7645 76.45%
CYP2D6 inhibition - 0.9418 94.18%
CYP1A2 inhibition - 0.7165 71.65%
CYP2C8 inhibition - 0.7291 72.91%
CYP inhibitory promiscuity - 0.9304 93.04%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8900 89.00%
Carcinogenicity (trinary) Non-required 0.5608 56.08%
Eye corrosion - 0.9817 98.17%
Eye irritation - 0.8742 87.42%
Skin irritation - 0.5525 55.25%
Skin corrosion - 0.9124 91.24%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5870 58.70%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.6375 63.75%
skin sensitisation - 0.6580 65.80%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity + 0.7700 77.00%
Acute Oral Toxicity (c) III 0.3316 33.16%
Estrogen receptor binding + 0.7022 70.22%
Androgen receptor binding + 0.5995 59.95%
Thyroid receptor binding + 0.5507 55.07%
Glucocorticoid receptor binding + 0.5934 59.34%
Aromatase binding + 0.5718 57.18%
PPAR gamma + 0.5239 52.39%
Honey bee toxicity - 0.6429 64.29%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9839 98.39%

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 98.16% 91.11%
CHEMBL2996 Q05655 Protein kinase C delta 97.53% 97.79%
CHEMBL221 P23219 Cyclooxygenase-1 97.50% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.93% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.65% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.51% 96.09%
CHEMBL2581 P07339 Cathepsin D 91.34% 98.95%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 90.33% 96.47%
CHEMBL253 P34972 Cannabinoid CB2 receptor 88.65% 97.25%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.50% 86.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.34% 91.07%
CHEMBL299 P17252 Protein kinase C alpha 85.03% 98.03%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.93% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.03% 97.09%
CHEMBL2413 P32246 C-C chemokine receptor type 1 83.39% 89.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.81% 95.50%
CHEMBL3267 P48736 PI3-kinase p110-gamma subunit 82.68% 95.71%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.36% 89.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 82.06% 96.77%
CHEMBL340 P08684 Cytochrome P450 3A4 81.51% 91.19%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 81.48% 97.21%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.38% 95.56%
CHEMBL5028 O14672 ADAM10 81.18% 97.50%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 80.89% 95.71%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.87% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.14% 95.89%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.03% 98.75%

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.
Helenium donianum

Cross-Links

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PubChem 162987956
LOTUS LTS0273077
wikiData Q104915009