[(1S,2S,6S,7R,8R,11R,13R,14S)-8-acetyloxy-14-hydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,12-dioxatetracyclo[8.4.0.02,6.011,13]tetradec-9-en-7-yl] (Z)-2-methylbut-2-enoate

Details

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Internal ID 98e6b664-9137-4394-9b34-04cd325a3a80
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(1S,2S,6S,7R,8R,11R,13R,14S)-8-acetyloxy-14-hydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,12-dioxatetracyclo[8.4.0.02,6.011,13]tetradec-9-en-7-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C2C(C3C(=C(C1OC(=O)C)C)C4C(C3(C)O)O4)OC(=O)C2=C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1[C@@H]2[C@@H]([C@@H]3C(=C([C@H]1OC(=O)C)C)[C@@H]4[C@H]([C@@]3(C)O)O4)OC(=O)C2=C
InChI InChI=1S/C22H26O8/c1-7-8(2)20(24)30-17-13-10(4)21(25)29-16(13)14-12(9(3)15(17)27-11(5)23)18-19(28-18)22(14,6)26/h7,13-19,26H,4H2,1-3,5-6H3/b8-7-/t13-,14-,15+,16-,17+,18+,19+,22-/m0/s1
InChI Key ASUISTIQHYLSGU-ACNOXPBPSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H26O8
Molecular Weight 418.40 g/mol
Exact Mass 418.16276778 g/mol
Topological Polar Surface Area (TPSA) 112.00 Ų
XlogP 0.50
Atomic LogP (AlogP) 1.37
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 [(1S,2S,6S,7R,8R,11R,13R,14S)-8-acetyloxy-14-hydroxy-9,14-dimethyl-5-methylidene-4-oxo-3,12-dioxatetracyclo[8.4.0.02,6.011,13]tetradec-9-en-7-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 + 0.9661 96.61%
Caco-2 - 0.5806 58.06%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.6806 68.06%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8476 84.76%
OATP1B3 inhibitior + 0.9030 90.30%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.7688 76.88%
P-glycoprotein inhibitior + 0.6390 63.90%
P-glycoprotein substrate - 0.5514 55.14%
CYP3A4 substrate + 0.6556 65.56%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9094 90.94%
CYP3A4 inhibition - 0.5166 51.66%
CYP2C9 inhibition - 0.9197 91.97%
CYP2C19 inhibition - 0.8338 83.38%
CYP2D6 inhibition - 0.9405 94.05%
CYP1A2 inhibition - 0.8466 84.66%
CYP2C8 inhibition - 0.6258 62.58%
CYP inhibitory promiscuity - 0.8709 87.09%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Danger 0.4280 42.80%
Eye corrosion - 0.9653 96.53%
Eye irritation - 0.7835 78.35%
Skin irritation - 0.6076 60.76%
Skin corrosion - 0.9089 90.89%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6008 60.08%
Micronuclear + 0.5700 57.00%
Hepatotoxicity + 0.6961 69.61%
skin sensitisation - 0.7036 70.36%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity + 0.7527 75.27%
Acute Oral Toxicity (c) III 0.3417 34.17%
Estrogen receptor binding + 0.7733 77.33%
Androgen receptor binding + 0.6162 61.62%
Thyroid receptor binding + 0.5818 58.18%
Glucocorticoid receptor binding + 0.5437 54.37%
Aromatase binding - 0.5244 52.44%
PPAR gamma + 0.6755 67.55%
Honey bee toxicity - 0.5825 58.25%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9411 94.11%

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 95.64% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.24% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.72% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.05% 89.00%
CHEMBL2581 P07339 Cathepsin D 88.38% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.65% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.19% 99.23%
CHEMBL3401 O75469 Pregnane X receptor 85.28% 94.73%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.09% 95.50%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.66% 97.14%
CHEMBL221 P23219 Cyclooxygenase-1 83.49% 90.17%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.45% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 82.07% 96.09%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 81.40% 97.21%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.37% 96.95%

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.
Heliopsis helianthoides

Cross-Links

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PubChem 14138870
LOTUS LTS0241820
wikiData Q104918068