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[(3aR,8S,8aS,9R,9aR)-8-acetyloxy-5,8a-dimethyl-1-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-9-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 76c7c3b9-5226-4d41-a295-368acd87aa0a
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
IUPAC Name [(3aR,8S,8aS,9R,9aR)-8-acetyloxy-5,8a-dimethyl-1-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-9-yl] 3-methylbutanoate
SMILES (Canonical) CC1=C2CCC(C2(C(C3C(C1)OC(=O)C3=C)OC(=O)CC(C)C)C)OC(=O)C
SMILES (Isomeric) CC1=C2CC[C@@H]([C@]2([C@@H]([C@H]3[C@@H](C1)OC(=O)C3=C)OC(=O)CC(C)C)C)OC(=O)C
InChI InChI=1S/C22H30O6/c1-11(2)9-18(24)28-20-19-13(4)21(25)27-16(19)10-12(3)15-7-8-17(22(15,20)6)26-14(5)23/h11,16-17,19-20H,4,7-10H2,1-3,5-6H3/t16-,17+,19-,20-,22+/m1/s1
InChI Key NIDWPWZFCXNRLD-POGPBNCUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H30O6
Molecular Weight 390.50 g/mol
Exact Mass 390.20423867 g/mol
Topological Polar Surface Area (TPSA) 78.90 Ų
XlogP 3.10
Atomic LogP (AlogP) 3.49
H-Bond Acceptor 6
H-Bond Donor 0
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,8S,8aS,9R,9aR)-8-acetyloxy-5,8a-dimethyl-1-methylidene-2-oxo-4,6,7,8,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-9-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 + 0.9885 98.85%
Caco-2 + 0.6545 65.45%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5000 50.00%
Subcellular localzation Mitochondria 0.6730 67.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8535 85.35%
OATP1B3 inhibitior - 0.3887 38.87%
MATE1 inhibitior - 0.7600 76.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior - 0.7036 70.36%
P-glycoprotein inhibitior + 0.6206 62.06%
P-glycoprotein substrate - 0.6811 68.11%
CYP3A4 substrate + 0.6620 66.20%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8935 89.35%
CYP3A4 inhibition - 0.6323 63.23%
CYP2C9 inhibition - 0.6295 62.95%
CYP2C19 inhibition - 0.6901 69.01%
CYP2D6 inhibition - 0.9482 94.82%
CYP1A2 inhibition + 0.6243 62.43%
CYP2C8 inhibition - 0.5668 56.68%
CYP inhibitory promiscuity - 0.8776 87.76%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8700 87.00%
Carcinogenicity (trinary) Non-required 0.6225 62.25%
Eye corrosion - 0.9750 97.50%
Eye irritation - 0.8080 80.80%
Skin irritation - 0.5143 51.43%
Skin corrosion - 0.9130 91.30%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5984 59.84%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.6013 60.13%
skin sensitisation - 0.7280 72.80%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.7875 78.75%
Nephrotoxicity + 0.8716 87.16%
Acute Oral Toxicity (c) III 0.5066 50.66%
Estrogen receptor binding + 0.7365 73.65%
Androgen receptor binding + 0.6213 62.13%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7849 78.49%
Aromatase binding + 0.5478 54.78%
PPAR gamma + 0.6760 67.60%
Honey bee toxicity - 0.7170 71.70%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9968 99.68%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.35% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.57% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.77% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.79% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.25% 95.56%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 89.28% 96.47%
CHEMBL2581 P07339 Cathepsin D 89.15% 98.95%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.76% 99.23%
CHEMBL2996 Q05655 Protein kinase C delta 86.97% 97.79%
CHEMBL221 P23219 Cyclooxygenase-1 85.54% 90.17%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 85.19% 98.75%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 84.01% 95.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.00% 97.14%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.63% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.73% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.20% 86.33%
CHEMBL340 P08684 Cytochrome P450 3A4 82.07% 91.19%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.97% 93.00%
CHEMBL3359 P21462 Formyl peptide receptor 1 81.93% 93.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.79% 89.00%
CHEMBL5103 Q969S8 Histone deacetylase 10 81.71% 90.08%
CHEMBL5028 O14672 ADAM10 81.52% 97.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.59% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.50% 92.62%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 80.24% 93.03%

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.
Wedelia grandiflora

Cross-Links

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PubChem 163194256
LOTUS LTS0210959
wikiData Q105179765