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[(3aR,4S,5R,6E,10E,11aS)-5-acetyloxy-3a-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-5,8,9,11a-tetrahydro-4H-cyclodeca[b]furan-4-yl] (2R,3R)-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 fae1000d-d838-4260-a5e2-a4c092d1dcfb
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4S,5R,6E,10E,11aS)-5-acetyloxy-3a-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-5,8,9,11a-tetrahydro-4H-cyclodeca[b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
SMILES (Canonical) CC1C(O1)(C)C(=O)OC2C(C(=CCCC(=CC3C2(C(=C)C(=O)O3)O)C)C)OC(=O)C
SMILES (Isomeric) C[C@@H]1[C@](O1)(C)C(=O)O[C@H]2[C@@H](/C(=C/CC/C(=C/[C@H]3[C@@]2(C(=C)C(=O)O3)O)/C)/C)OC(=O)C
InChI InChI=1S/C22H28O8/c1-11-8-7-9-12(2)17(27-15(5)23)18(29-20(25)21(6)14(4)30-21)22(26)13(3)19(24)28-16(22)10-11/h9-10,14,16-18,26H,3,7-8H2,1-2,4-6H3/b11-10+,12-9+/t14-,16+,17-,18+,21-,22-/m1/s1
InChI Key OZRDSBAJYKLXCX-AGXHWNHCSA-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) 112.00 Ų
XlogP 1.10
Atomic LogP (AlogP) 1.91
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,5R,6E,10E,11aS)-5-acetyloxy-3a-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-5,8,9,11a-tetrahydro-4H-cyclodeca[b]furan-4-yl] (2R,3R)-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 + 0.9709 97.09%
Caco-2 + 0.5338 53.38%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.5670 56.70%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9108 91.08%
OATP1B3 inhibitior + 0.8749 87.49%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7771 77.71%
BSEP inhibitior + 0.6751 67.51%
P-glycoprotein inhibitior + 0.7460 74.60%
P-glycoprotein substrate - 0.6765 67.65%
CYP3A4 substrate + 0.6703 67.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8831 88.31%
CYP3A4 inhibition - 0.6565 65.65%
CYP2C9 inhibition - 0.8259 82.59%
CYP2C19 inhibition - 0.8664 86.64%
CYP2D6 inhibition - 0.9273 92.73%
CYP1A2 inhibition + 0.6029 60.29%
CYP2C8 inhibition - 0.6390 63.90%
CYP inhibitory promiscuity - 0.9269 92.69%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4429 44.29%
Eye corrosion - 0.9749 97.49%
Eye irritation - 0.8908 89.08%
Skin irritation - 0.5291 52.91%
Skin corrosion - 0.8408 84.08%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6255 62.55%
Micronuclear - 0.6100 61.00%
Hepatotoxicity + 0.6002 60.02%
skin sensitisation - 0.7018 70.18%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.5444 54.44%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.6288 62.88%
Acute Oral Toxicity (c) III 0.4830 48.30%
Estrogen receptor binding + 0.7551 75.51%
Androgen receptor binding + 0.6013 60.13%
Thyroid receptor binding + 0.5852 58.52%
Glucocorticoid receptor binding + 0.7592 75.92%
Aromatase binding + 0.6271 62.71%
PPAR gamma + 0.7446 74.46%
Honey bee toxicity - 0.7544 75.44%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9694 96.94%

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 98.63% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.44% 97.25%
CHEMBL2581 P07339 Cathepsin D 92.98% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.05% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.26% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.45% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.25% 95.56%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 87.23% 81.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.96% 94.45%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.85% 95.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.29% 94.00%
CHEMBL230 P35354 Cyclooxygenase-2 85.18% 89.63%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.07% 89.00%
CHEMBL340 P08684 Cytochrome P450 3A4 83.36% 91.19%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.88% 93.03%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.87% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.87% 100.00%
CHEMBL4208 P20618 Proteasome component C5 80.18% 90.00%

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.
Montanoa hibiscifolia

Cross-Links

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PubChem 162923567
LOTUS LTS0176100
wikiData Q105204044