[(3aR,4R,6S,8Z,10R,11S,11aS)-6-acetyloxy-11-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate

Details

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Internal ID 7c0350c1-8abc-494a-80e0-a7415c6812ea
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4R,6S,8Z,10R,11S,11aS)-6-acetyloxy-11-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(C(=O)C=CC(C(C2C1C(=C)C(=O)O2)O)C)(C)OC(=O)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1C[C@](C(=O)/C=C\[C@H]([C@@H]([C@@H]2[C@@H]1C(=C)C(=O)O2)O)C)(C)OC(=O)C
InChI InChI=1S/C22H28O8/c1-7-11(2)20(26)28-15-10-22(6,30-14(5)23)16(24)9-8-12(3)18(25)19-17(15)13(4)21(27)29-19/h7-9,12,15,17-19,25H,4,10H2,1-3,5-6H3/b9-8-,11-7-/t12-,15-,17-,18+,19+,22+/m1/s1
InChI Key NROPEXBVWKMTHZ-FABACOQKSA-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) 116.00 Ų
XlogP 2.40
Atomic LogP (AlogP) 1.81
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,4R,6S,8Z,10R,11S,11aS)-6-acetyloxy-11-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (Z)-2-methylbut-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 + 0.9738 97.38%
Caco-2 + 0.5268 52.68%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.5589 55.89%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8481 84.81%
OATP1B3 inhibitior + 0.8521 85.21%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8420 84.20%
P-glycoprotein inhibitior + 0.7167 71.67%
P-glycoprotein substrate - 0.6148 61.48%
CYP3A4 substrate + 0.6684 66.84%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9088 90.88%
CYP3A4 inhibition - 0.6461 64.61%
CYP2C9 inhibition - 0.9169 91.69%
CYP2C19 inhibition - 0.9029 90.29%
CYP2D6 inhibition - 0.9656 96.56%
CYP1A2 inhibition - 0.7169 71.69%
CYP2C8 inhibition - 0.6022 60.22%
CYP inhibitory promiscuity - 0.9300 93.00%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9143 91.43%
Carcinogenicity (trinary) Non-required 0.4145 41.45%
Eye corrosion - 0.9635 96.35%
Eye irritation - 0.9277 92.77%
Skin irritation - 0.5969 59.69%
Skin corrosion - 0.9026 90.26%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4737 47.37%
Micronuclear - 0.5600 56.00%
Hepatotoxicity + 0.6302 63.02%
skin sensitisation - 0.5953 59.53%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.5889 58.89%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.6814 68.14%
Acute Oral Toxicity (c) III 0.3971 39.71%
Estrogen receptor binding + 0.7328 73.28%
Androgen receptor binding + 0.6135 61.35%
Thyroid receptor binding + 0.5884 58.84%
Glucocorticoid receptor binding + 0.7042 70.42%
Aromatase binding - 0.5729 57.29%
PPAR gamma + 0.6643 66.43%
Honey bee toxicity - 0.6184 61.84%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5400 54.00%
Fish aquatic toxicity + 0.9390 93.90%

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 98.81% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 92.66% 90.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 92.49% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.17% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.95% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.92% 86.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 89.34% 91.07%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.42% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.10% 99.23%
CHEMBL2581 P07339 Cathepsin D 84.73% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.62% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.62% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 83.50% 94.73%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.15% 97.14%

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.
Piptolepis ericoides

Cross-Links

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PubChem 162986557
LOTUS LTS0239677
wikiData Q105184699