[(3aS,4S,5S,6E,10Z,11aR)-6-formyl-5-methoxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate

Details

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Internal ID 3088cc83-d162-4dc7-b290-e99c8e1fadab
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aS,4S,5S,6E,10Z,11aR)-6-formyl-5-methoxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate
SMILES (Canonical) CC1=CC2C(C(C(C(=CCC1)C=O)OC)OC(=O)C(C)C)C(=C)C(=O)O2
SMILES (Isomeric) C/C/1=C/[C@@H]2[C@@H]([C@@H]([C@H](/C(=C\CC1)/C=O)OC)OC(=O)C(C)C)C(=C)C(=O)O2
InChI InChI=1S/C20H26O6/c1-11(2)19(22)26-18-16-13(4)20(23)25-15(16)9-12(3)7-6-8-14(10-21)17(18)24-5/h8-11,15-18H,4,6-7H2,1-3,5H3/b12-9-,14-8-/t15-,16+,17+,18+/m1/s1
InChI Key SKCDPGIEMVQDCR-VBMXKYFYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H26O6
Molecular Weight 362.40 g/mol
Exact Mass 362.17293854 g/mol
Topological Polar Surface Area (TPSA) 78.90 Ų
XlogP 2.20
Atomic LogP (AlogP) 2.53
H-Bond Acceptor 6
H-Bond Donor 0
Rotatable Bonds 4

Synonyms

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75744-64-8
[(3aS,4S,5S,6E,10E,11aR)-6-formyl-5-methoxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate

2D Structure

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2D Structure of [(3aS,4S,5S,6E,10Z,11aR)-6-formyl-5-methoxy-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9870 98.70%
Caco-2 + 0.7510 75.10%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.5652 56.52%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8619 86.19%
OATP1B3 inhibitior + 0.8933 89.33%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.5896 58.96%
P-glycoprotein inhibitior + 0.6341 63.41%
P-glycoprotein substrate - 0.7240 72.40%
CYP3A4 substrate + 0.6140 61.40%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9012 90.12%
CYP3A4 inhibition - 0.7389 73.89%
CYP2C9 inhibition - 0.8364 83.64%
CYP2C19 inhibition - 0.7189 71.89%
CYP2D6 inhibition - 0.9080 90.80%
CYP1A2 inhibition + 0.6259 62.59%
CYP2C8 inhibition - 0.6880 68.80%
CYP inhibitory promiscuity - 0.8483 84.83%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.8600 86.00%
Carcinogenicity (trinary) Non-required 0.5719 57.19%
Eye corrosion - 0.9351 93.51%
Eye irritation - 0.8970 89.70%
Skin irritation - 0.6859 68.59%
Skin corrosion - 0.9324 93.24%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6737 67.37%
Micronuclear - 0.8100 81.00%
Hepatotoxicity + 0.6918 69.18%
skin sensitisation - 0.7036 70.36%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity - 0.5333 53.33%
Mitochondrial toxicity + 0.7000 70.00%
Nephrotoxicity + 0.5568 55.68%
Acute Oral Toxicity (c) III 0.4496 44.96%
Estrogen receptor binding + 0.7354 73.54%
Androgen receptor binding + 0.5516 55.16%
Thyroid receptor binding - 0.5237 52.37%
Glucocorticoid receptor binding + 0.7432 74.32%
Aromatase binding + 0.5478 54.78%
PPAR gamma + 0.6314 63.14%
Honey bee toxicity - 0.6654 66.54%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9735 97.35%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.05% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.92% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.12% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.26% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.02% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 87.22% 94.73%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.89% 99.23%
CHEMBL2581 P07339 Cathepsin D 83.23% 98.95%
CHEMBL3714130 P46095 G-protein coupled receptor 6 82.88% 97.36%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.45% 89.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.33% 93.03%
CHEMBL4040 P28482 MAP kinase ERK2 81.96% 83.82%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.63% 95.50%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.06% 86.33%
CHEMBL4208 P20618 Proteasome component C5 80.69% 90.00%
CHEMBL5028 O14672 ADAM10 80.24% 97.50%

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.
Acanthospermum australe

Cross-Links

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PubChem 93959096
LOTUS LTS0062693
wikiData Q105254727