[(3aS,4S,5S,6Z,10Z,11aR)-5-acetyloxy-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate

Details

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Internal ID 89e5791e-0e31-4946-be63-a7dd78c33090
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aS,4S,5S,6Z,10Z,11aR)-5-acetyloxy-6,10-bis(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-methylpropanoate
SMILES (Canonical) CC(C)C(=O)OC1C2C(C=C(CCC=C(C1OC(=O)C)CO)CO)OC(=O)C2=C
SMILES (Isomeric) CC(C)C(=O)O[C@H]1[C@@H]2[C@@H](/C=C(/CC/C=C(\[C@@H]1OC(=O)C)/CO)\CO)OC(=O)C2=C
InChI InChI=1S/C21H28O8/c1-11(2)20(25)29-19-17-12(3)21(26)28-16(17)8-14(9-22)6-5-7-15(10-23)18(19)27-13(4)24/h7-8,11,16-19,22-23H,3,5-6,9-10H2,1-2,4H3/b14-8-,15-7-/t16-,17+,18+,19+/m1/s1
InChI Key YOXQRQIFAYSGMZ-AMVJFLEGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C21H28O8
Molecular Weight 408.40 g/mol
Exact Mass 408.17841785 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 0.40
Atomic LogP (AlogP) 1.21
H-Bond Acceptor 8
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,4S,5S,6Z,10Z,11aR)-5-acetyloxy-6,10-bis(hydroxymethyl)-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 + 0.9112 91.12%
Caco-2 - 0.6764 67.64%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.8234 82.34%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8850 88.50%
OATP1B3 inhibitior + 0.9312 93.12%
MATE1 inhibitior - 0.8812 88.12%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior - 0.4816 48.16%
P-glycoprotein inhibitior - 0.4832 48.32%
P-glycoprotein substrate - 0.6779 67.79%
CYP3A4 substrate + 0.6073 60.73%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8889 88.89%
CYP3A4 inhibition - 0.7739 77.39%
CYP2C9 inhibition - 0.6770 67.70%
CYP2C19 inhibition - 0.6978 69.78%
CYP2D6 inhibition - 0.8743 87.43%
CYP1A2 inhibition - 0.5838 58.38%
CYP2C8 inhibition - 0.6790 67.90%
CYP inhibitory promiscuity - 0.7944 79.44%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 0.9443 94.43%
Carcinogenicity (trinary) Non-required 0.6235 62.35%
Eye corrosion - 0.9699 96.99%
Eye irritation - 0.8257 82.57%
Skin irritation - 0.7182 71.82%
Skin corrosion - 0.9430 94.30%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5754 57.54%
Micronuclear - 0.8600 86.00%
Hepatotoxicity + 0.5500 55.00%
skin sensitisation - 0.8289 82.89%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.5778 57.78%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.6359 63.59%
Acute Oral Toxicity (c) III 0.5299 52.99%
Estrogen receptor binding + 0.6639 66.39%
Androgen receptor binding + 0.5547 55.47%
Thyroid receptor binding - 0.6230 62.30%
Glucocorticoid receptor binding + 0.6985 69.85%
Aromatase binding - 0.5926 59.26%
PPAR gamma - 0.5865 58.65%
Honey bee toxicity - 0.7514 75.14%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6800 68.00%
Fish aquatic toxicity + 0.9698 96.98%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.06% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.09% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.23% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.29% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.15% 95.56%
CHEMBL2581 P07339 Cathepsin D 88.65% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 86.39% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.93% 89.00%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 84.28% 98.75%
CHEMBL3137262 O60341 LSD1/CoREST complex 81.76% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.67% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.42% 99.23%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.98% 86.33%

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 hispidum

Cross-Links

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PubChem 163018699
LOTUS LTS0261390
wikiData Q105351586