[(3aR,4S,6Z,10E,11aR)-6-(acetyloxymethyl)-10-formyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

Details

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Internal ID 9aae0998-e5e0-478c-840b-2b7b077c07a2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aR,4S,6Z,10E,11aR)-6-(acetyloxymethyl)-10-formyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
SMILES (Canonical) CC(=O)OCC1=CCCC(=CC2C(C(C1)OC(=O)C(=C)CO)C(=C)C(=O)O2)C=O
SMILES (Isomeric) CC(=O)OC/C/1=C\CC/C(=C\[C@@H]2[C@@H]([C@H](C1)OC(=O)C(=C)CO)C(=C)C(=O)O2)/C=O
InChI InChI=1S/C21H24O8/c1-12(9-22)20(25)28-18-8-16(11-27-14(3)24)6-4-5-15(10-23)7-17-19(18)13(2)21(26)29-17/h6-7,10,17-19,22H,1-2,4-5,8-9,11H2,3H3/b15-7+,16-6-/t17-,18+,19+/m1/s1
InChI Key NVEYSKFDXKUOIS-KNFZQGANSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H24O8
Molecular Weight 404.40 g/mol
Exact Mass 404.14711772 g/mol
Topological Polar Surface Area (TPSA) 116.00 Ų
XlogP 0.70
Atomic LogP (AlogP) 1.34
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,6Z,10E,11aR)-6-(acetyloxymethyl)-10-formyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-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 + 0.9794 97.94%
Caco-2 - 0.7065 70.65%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.7346 73.46%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8566 85.66%
OATP1B3 inhibitior + 0.9441 94.41%
MATE1 inhibitior - 0.8412 84.12%
OCT2 inhibitior - 0.6500 65.00%
BSEP inhibitior + 0.6341 63.41%
P-glycoprotein inhibitior + 0.5927 59.27%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6706 67.06%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9017 90.17%
CYP3A4 inhibition - 0.8743 87.43%
CYP2C9 inhibition - 0.8887 88.87%
CYP2C19 inhibition - 0.8199 81.99%
CYP2D6 inhibition - 0.9145 91.45%
CYP1A2 inhibition - 0.5945 59.45%
CYP2C8 inhibition + 0.4924 49.24%
CYP inhibitory promiscuity - 0.9026 90.26%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6790 67.90%
Eye corrosion - 0.9426 94.26%
Eye irritation - 0.7740 77.40%
Skin irritation - 0.6202 62.02%
Skin corrosion - 0.9163 91.63%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4031 40.31%
Micronuclear - 0.8300 83.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.7944 79.44%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.5222 52.22%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.7063 70.63%
Acute Oral Toxicity (c) III 0.6358 63.58%
Estrogen receptor binding + 0.5499 54.99%
Androgen receptor binding + 0.5466 54.66%
Thyroid receptor binding - 0.5675 56.75%
Glucocorticoid receptor binding + 0.6953 69.53%
Aromatase binding - 0.5408 54.08%
PPAR gamma + 0.5569 55.69%
Honey bee toxicity - 0.6590 65.90%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9501 95.01%

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 97.75% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 96.82% 91.49%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.60% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.45% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.61% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.02% 99.17%
CHEMBL2581 P07339 Cathepsin D 86.27% 98.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.13% 95.50%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.18% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.01% 100.00%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 82.21% 97.33%
CHEMBL5028 O14672 ADAM10 81.83% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.26% 95.89%
CHEMBL4208 P20618 Proteasome component C5 81.03% 90.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.96% 89.00%
CHEMBL253 P34972 Cannabinoid CB2 receptor 80.83% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.49% 97.09%
CHEMBL217 P14416 Dopamine D2 receptor 80.16% 95.62%

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.
Calea pilosa
Calea villosa
Distephanus angulifolius
Pseudostifftia kingii
Ursinia nana

Cross-Links

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PubChem 42646678
LOTUS LTS0267162
wikiData Q105367704