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[(3aR,4S,5S,6R,6aS,7R,9aR,9bR)-5-acetyloxy-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl] (E)-2-(acetyloxymethyl)but-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 8af764f5-4f1a-4a63-92fc-6db9082e0f48
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4S,5S,6R,6aS,7R,9aR,9bR)-5-acetyloxy-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl] (E)-2-(acetyloxymethyl)but-2-enoate
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C24H28O10/c1-6-14(8-30-12(4)25)23(29)34-20-17-11(3)22(28)33-19(17)16-10(2)7-15(27)18(16)24(9-31-24)21(20)32-13(5)26/h6-7,15-21,27H,3,8-9H2,1-2,4-5H3/b14-6+/t15-,16+,17-,18-,19-,20+,21+,24+/m1/s1
InChI Key VTRRMLSZDNELCV-IRUPESJBSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C24H28O10
Molecular Weight 476.50 g/mol
Exact Mass 476.16824709 g/mol
Topological Polar Surface Area (TPSA) 138.00 Ų
XlogP 0.30
Atomic LogP (AlogP) 0.77
H-Bond Acceptor 10
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 [(3aR,4S,5S,6R,6aS,7R,9aR,9bR)-5-acetyloxy-7-hydroxy-9-methyl-3-methylidene-2-oxospiro[4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-6,2'-oxirane]-4-yl] (E)-2-(acetyloxymethyl)but-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 + 0.9386 93.86%
Caco-2 - 0.7377 73.77%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.6056 60.56%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8448 84.48%
OATP1B3 inhibitior + 0.9181 91.81%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8632 86.32%
P-glycoprotein inhibitior + 0.7344 73.44%
P-glycoprotein substrate - 0.5117 51.17%
CYP3A4 substrate + 0.6455 64.55%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8956 89.56%
CYP3A4 inhibition - 0.7916 79.16%
CYP2C9 inhibition - 0.7956 79.56%
CYP2C19 inhibition - 0.7463 74.63%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.7666 76.66%
CYP2C8 inhibition - 0.5692 56.92%
CYP inhibitory promiscuity - 0.8479 84.79%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.5767 57.67%
Eye corrosion - 0.9718 97.18%
Eye irritation - 0.8788 87.88%
Skin irritation - 0.6394 63.94%
Skin corrosion - 0.9118 91.18%
Ames mutagenesis - 0.7278 72.78%
Human Ether-a-go-go-Related Gene inhibition - 0.6462 64.62%
Micronuclear - 0.5900 59.00%
Hepatotoxicity + 0.6553 65.53%
skin sensitisation - 0.6712 67.12%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.5556 55.56%
Mitochondrial toxicity + 0.7500 75.00%
Nephrotoxicity + 0.8522 85.22%
Acute Oral Toxicity (c) III 0.3119 31.19%
Estrogen receptor binding + 0.7518 75.18%
Androgen receptor binding + 0.6383 63.83%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7231 72.31%
Aromatase binding - 0.5255 52.55%
PPAR gamma + 0.6374 63.74%
Honey bee toxicity - 0.6777 67.77%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9554 95.54%

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 97.43% 91.11%
CHEMBL2581 P07339 Cathepsin D 93.57% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.56% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.05% 86.33%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 91.65% 89.34%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.70% 95.56%
CHEMBL2996 Q05655 Protein kinase C delta 89.95% 97.79%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.15% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.67% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.63% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 85.99% 97.36%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.98% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.85% 99.23%
CHEMBL3401 O75469 Pregnane X receptor 85.68% 94.73%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.64% 95.50%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.56% 85.14%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.53% 95.89%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.24% 91.07%
CHEMBL230 P35354 Cyclooxygenase-2 84.07% 89.63%
CHEMBL5028 O14672 ADAM10 83.97% 97.50%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 83.45% 97.21%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.44% 97.25%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.49% 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.
Stylotrichium rotundifolium

Cross-Links

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PubChem 162864904
LOTUS LTS0275153
wikiData Q105292963