[(1R,2E,4S,8R,9R,11R,12S)-1,12-dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (2S)-2-methylbutanoate

Details

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Internal ID fda077f7-a1de-4eed-aace-a3f7fc81de18
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name [(1R,2E,4S,8R,9R,11R,12S)-1,12-dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (2S)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1CC2(C(CC(O2)(C(=CC3C1C(=C)C(=O)O3)CO)O)O)C
SMILES (Isomeric) CC[C@H](C)C(=O)O[C@@H]1C[C@@]2([C@H](C[C@@](O2)(/C(=C/[C@H]3[C@@H]1C(=C)C(=O)O3)/CO)O)O)C
InChI InChI=1S/C20H28O8/c1-5-10(2)17(23)27-14-7-19(4)15(22)8-20(25,28-19)12(9-21)6-13-16(14)11(3)18(24)26-13/h6,10,13-16,21-22,25H,3,5,7-9H2,1-2,4H3/b12-6+/t10-,13-,14+,15-,16-,19+,20+/m0/s1
InChI Key PBHKMDBIOFKKFO-GVNZZBAOSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H28O8
Molecular Weight 396.40 g/mol
Exact Mass 396.17841785 g/mol
Topological Polar Surface Area (TPSA) 123.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 0.59
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,2E,4S,8R,9R,11R,12S)-1,12-dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.04,8]tetradec-2-en-9-yl] (2S)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9581 95.81%
Caco-2 - 0.5986 59.86%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.6111 61.11%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8675 86.75%
OATP1B3 inhibitior + 0.9546 95.46%
MATE1 inhibitior - 0.9212 92.12%
OCT2 inhibitior - 0.9114 91.14%
BSEP inhibitior - 0.5869 58.69%
P-glycoprotein inhibitior - 0.6826 68.26%
P-glycoprotein substrate - 0.5718 57.18%
CYP3A4 substrate + 0.6499 64.99%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8860 88.60%
CYP3A4 inhibition + 0.5816 58.16%
CYP2C9 inhibition - 0.7821 78.21%
CYP2C19 inhibition - 0.8649 86.49%
CYP2D6 inhibition - 0.9474 94.74%
CYP1A2 inhibition - 0.8546 85.46%
CYP2C8 inhibition - 0.6058 60.58%
CYP inhibitory promiscuity - 0.8984 89.84%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5485 54.85%
Eye corrosion - 0.9877 98.77%
Eye irritation - 0.9359 93.59%
Skin irritation + 0.4917 49.17%
Skin corrosion - 0.9392 93.92%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4188 41.88%
Micronuclear - 0.7400 74.00%
Hepatotoxicity + 0.6250 62.50%
skin sensitisation - 0.8888 88.88%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity - 0.7043 70.43%
Acute Oral Toxicity (c) III 0.5079 50.79%
Estrogen receptor binding + 0.8398 83.98%
Androgen receptor binding + 0.5936 59.36%
Thyroid receptor binding + 0.6233 62.33%
Glucocorticoid receptor binding + 0.8320 83.20%
Aromatase binding + 0.5859 58.59%
PPAR gamma + 0.5652 56.52%
Honey bee toxicity - 0.7633 76.33%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 0.9825 98.25%

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
CHEMBL221 P23219 Cyclooxygenase-1 95.47% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.92% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 92.31% 83.82%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 91.81% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.78% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 91.58% 97.79%
CHEMBL2581 P07339 Cathepsin D 91.24% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.41% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.79% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.54% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.18% 95.56%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.74% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.68% 89.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.60% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.39% 95.89%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 80.13% 95.71%

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.
Aldama bracteata

Cross-Links

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PubChem 162952848
LOTUS LTS0240012
wikiData Q105205191