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[(3aR,4S,4aS,5S,8S,8aR,9aS)-4-acetyloxy-8a-methyl-3-methylidene-2-oxospiro[3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-5,2'-oxirane]-8-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

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 c1202893-a94b-4251-bd04-c232a4430ccb
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,4aS,5S,8S,8aR,9aS)-4-acetyloxy-8a-methyl-3-methylidene-2-oxospiro[3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-5,2'-oxirane]-8-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
SMILES (Canonical) CC1C(O1)(C)C(=O)OC2CCC3(CO3)C4C2(CC5C(C4OC(=O)C)C(=C)C(=O)O5)C
SMILES (Isomeric) C[C@H]1[C@@](O1)(C)C(=O)O[C@H]2CC[C@@]3(CO3)[C@H]4[C@]2(C[C@H]5[C@H]([C@@H]4OC(=O)C)C(=C)C(=O)O5)C
InChI InChI=1S/C22H28O8/c1-10-15-13(28-18(10)24)8-20(4)14(29-19(25)21(5)11(2)30-21)6-7-22(9-26-22)17(20)16(15)27-12(3)23/h11,13-17H,1,6-9H2,2-5H3/t11-,13-,14-,15+,16-,17+,20-,21-,22+/m0/s1
InChI Key CMZLEIIWKXKLMG-FSQLGYFPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28O8
Molecular Weight 420.50 g/mol
Exact Mass 420.17841785 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 1.90
Atomic LogP (AlogP) 1.69
H-Bond Acceptor 8
H-Bond Donor 0
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,4aS,5S,8S,8aR,9aS)-4-acetyloxy-8a-methyl-3-methylidene-2-oxospiro[3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-5,2'-oxirane]-8-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9875 98.75%
Caco-2 + 0.5000 50.00%
Blood Brain Barrier + 0.8000 80.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7758 77.58%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8780 87.80%
OATP1B3 inhibitior + 0.9368 93.68%
MATE1 inhibitior - 0.8200 82.00%
OCT2 inhibitior - 0.5250 52.50%
BSEP inhibitior - 0.4762 47.62%
P-glycoprotein inhibitior - 0.4640 46.40%
P-glycoprotein substrate - 0.7036 70.36%
CYP3A4 substrate + 0.6849 68.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8834 88.34%
CYP3A4 inhibition - 0.6843 68.43%
CYP2C9 inhibition - 0.8305 83.05%
CYP2C19 inhibition - 0.8692 86.92%
CYP2D6 inhibition - 0.9402 94.02%
CYP1A2 inhibition - 0.6448 64.48%
CYP2C8 inhibition - 0.6008 60.08%
CYP inhibitory promiscuity - 0.8615 86.15%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5348 53.48%
Eye corrosion - 0.9850 98.50%
Eye irritation - 0.8941 89.41%
Skin irritation - 0.5435 54.35%
Skin corrosion - 0.9141 91.41%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4533 45.33%
Micronuclear - 0.6100 61.00%
Hepatotoxicity + 0.6835 68.35%
skin sensitisation - 0.8087 80.87%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity + 0.7160 71.60%
Acute Oral Toxicity (c) III 0.4898 48.98%
Estrogen receptor binding + 0.8247 82.47%
Androgen receptor binding + 0.6762 67.62%
Thyroid receptor binding + 0.5764 57.64%
Glucocorticoid receptor binding + 0.6598 65.98%
Aromatase binding + 0.5990 59.90%
PPAR gamma + 0.7302 73.02%
Honey bee toxicity - 0.7630 76.30%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5250 52.50%
Fish aquatic toxicity + 0.9967 99.67%

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 94.95% 91.11%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 93.45% 99.23%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.67% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.64% 85.14%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 89.28% 97.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.84% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 88.79% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.87% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.47% 89.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 86.47% 82.69%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.35% 95.89%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.80% 94.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.71% 92.94%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 85.18% 93.03%
CHEMBL3922 P50579 Methionine aminopeptidase 2 85.01% 97.28%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.94% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.71% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.11% 96.09%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 82.76% 94.42%
CHEMBL221 P23219 Cyclooxygenase-1 82.32% 90.17%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.15% 94.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 81.60% 97.25%
CHEMBL259 P32245 Melanocortin receptor 4 81.55% 95.38%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 81.00% 98.99%
CHEMBL5255 O00206 Toll-like receptor 4 80.59% 92.50%
CHEMBL2581 P07339 Cathepsin D 80.46% 98.95%

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.
Dimerostemma asperatum

Cross-Links

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PubChem 162843563
LOTUS LTS0086207
wikiData Q104965461