[(1R,2S,3R,7S,8S,9S,13S)-9-acetyloxy-13-(hydroxymethyl)-6-methylidene-5-oxo-4,12-dioxatetracyclo[8.5.0.02,13.03,7]pentadec-10-en-8-yl] (Z)-2-methylbut-2-enoate

Details

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Internal ID 761c6f14-16df-4c04-bd5c-c79d5b1aab5d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(1R,2S,3R,7S,8S,9S,13S)-9-acetyloxy-13-(hydroxymethyl)-6-methylidene-5-oxo-4,12-dioxatetracyclo[8.5.0.02,13.03,7]pentadec-10-en-8-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1C2C(C3C4CCC3(OC=C4C1OC(=O)C)CO)OC(=O)C2=C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@H]([C@@H]3[C@H]4CC[C@@]3(OC=C4[C@@H]1OC(=O)C)CO)OC(=O)C2=C
InChI InChI=1S/C22H26O8/c1-5-10(2)20(25)30-19-15-11(3)21(26)29-18(15)16-13-6-7-22(16,9-23)27-8-14(13)17(19)28-12(4)24/h5,8,13,15-19,23H,3,6-7,9H2,1-2,4H3/b10-5-/t13-,15-,16-,17-,18+,19-,22+/m0/s1
InChI Key NZVIXXXLIPEQIO-BKYRMVCVSA-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) 108.00 Ų
XlogP 1.10
Atomic LogP (AlogP) 1.58
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,2S,3R,7S,8S,9S,13S)-9-acetyloxy-13-(hydroxymethyl)-6-methylidene-5-oxo-4,12-dioxatetracyclo[8.5.0.02,13.03,7]pentadec-10-en-8-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 + 0.9308 93.08%
Caco-2 - 0.6443 64.43%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.8684 86.84%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7822 78.22%
OATP1B3 inhibitior + 0.8929 89.29%
MATE1 inhibitior - 0.8012 80.12%
OCT2 inhibitior - 0.6771 67.71%
BSEP inhibitior - 0.5000 50.00%
P-glycoprotein inhibitior + 0.5958 59.58%
P-glycoprotein substrate - 0.5388 53.88%
CYP3A4 substrate + 0.6598 65.98%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9026 90.26%
CYP3A4 inhibition - 0.8172 81.72%
CYP2C9 inhibition - 0.8148 81.48%
CYP2C19 inhibition - 0.8640 86.40%
CYP2D6 inhibition - 0.9432 94.32%
CYP1A2 inhibition - 0.7990 79.90%
CYP2C8 inhibition + 0.4567 45.67%
CYP inhibitory promiscuity - 0.8914 89.14%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5746 57.46%
Eye corrosion - 0.9791 97.91%
Eye irritation - 0.9060 90.60%
Skin irritation - 0.6169 61.69%
Skin corrosion - 0.9342 93.42%
Ames mutagenesis - 0.6370 63.70%
Human Ether-a-go-go-Related Gene inhibition - 0.4710 47.10%
Micronuclear - 0.8400 84.00%
Hepatotoxicity + 0.5302 53.02%
skin sensitisation - 0.8664 86.64%
Respiratory toxicity + 0.6889 68.89%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.7837 78.37%
Acute Oral Toxicity (c) III 0.4631 46.31%
Estrogen receptor binding + 0.6976 69.76%
Androgen receptor binding + 0.6726 67.26%
Thyroid receptor binding + 0.5533 55.33%
Glucocorticoid receptor binding + 0.6519 65.19%
Aromatase binding - 0.5416 54.16%
PPAR gamma + 0.6019 60.19%
Honey bee toxicity - 0.6766 67.66%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9272 92.72%

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 96.95% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.54% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.19% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.87% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.84% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.48% 95.56%
CHEMBL2581 P07339 Cathepsin D 90.18% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.16% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.12% 86.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.92% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.42% 99.23%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 84.94% 94.62%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.88% 100.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 81.73% 93.03%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.95% 93.04%

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 162816038
LOTUS LTS0152200
wikiData Q105188470