(3R,3aR,4R,6S,9E,11R,11aS)-11-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-4-[(2S)-2-methylbutoxy]-3a,4,5,6,7,8,11,11a-octahydro-3H-cyclodeca[b]furan-2-one

Details

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Internal ID c42c346e-8067-40f4-b7d3-b967f1184859
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name (3R,3aR,4R,6S,9E,11R,11aS)-11-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-4-[(2S)-2-methylbutoxy]-3a,4,5,6,7,8,11,11a-octahydro-3H-cyclodeca[b]furan-2-one
SMILES (Canonical) CCC(C)COC1CC(CCC=C(C(C2C1C(C(=O)O2)C)O)C)CO
SMILES (Isomeric) CC[C@H](C)CO[C@@H]1C[C@H](CC/C=C(/[C@H]([C@@H]2[C@@H]1[C@H](C(=O)O2)C)O)\C)CO
InChI InChI=1S/C20H34O5/c1-5-12(2)11-24-16-9-15(10-21)8-6-7-13(3)18(22)19-17(16)14(4)20(23)25-19/h7,12,14-19,21-22H,5-6,8-11H2,1-4H3/b13-7+/t12-,14+,15-,16+,17+,18+,19-/m0/s1
InChI Key IWFZPNVCTDXDMP-TVOYGJSRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H34O5
Molecular Weight 354.50 g/mol
Exact Mass 354.24062418 g/mol
Topological Polar Surface Area (TPSA) 76.00 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.70
H-Bond Acceptor 5
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 (3R,3aR,4R,6S,9E,11R,11aS)-11-hydroxy-6-(hydroxymethyl)-3,10-dimethyl-4-[(2S)-2-methylbutoxy]-3a,4,5,6,7,8,11,11a-octahydro-3H-cyclodeca[b]furan-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9694 96.94%
Caco-2 + 0.6762 67.62%
Blood Brain Barrier + 0.6750 67.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.6689 66.89%
OATP2B1 inhibitior - 0.8600 86.00%
OATP1B1 inhibitior + 0.8970 89.70%
OATP1B3 inhibitior + 0.9505 95.05%
MATE1 inhibitior - 0.9412 94.12%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior - 0.6897 68.97%
P-glycoprotein inhibitior - 0.7407 74.07%
P-glycoprotein substrate - 0.5875 58.75%
CYP3A4 substrate + 0.5901 59.01%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8473 84.73%
CYP3A4 inhibition - 0.5465 54.65%
CYP2C9 inhibition - 0.7814 78.14%
CYP2C19 inhibition - 0.6644 66.44%
CYP2D6 inhibition - 0.9027 90.27%
CYP1A2 inhibition - 0.5514 55.14%
CYP2C8 inhibition - 0.8109 81.09%
CYP inhibitory promiscuity - 0.6887 68.87%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5799 57.99%
Eye corrosion - 0.9871 98.71%
Eye irritation - 0.9643 96.43%
Skin irritation - 0.6175 61.75%
Skin corrosion - 0.9422 94.22%
Ames mutagenesis - 0.6970 69.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6538 65.38%
Micronuclear - 0.9000 90.00%
Hepatotoxicity + 0.5676 56.76%
skin sensitisation - 0.9157 91.57%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.6111 61.11%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity + 0.5705 57.05%
Acute Oral Toxicity (c) III 0.5345 53.45%
Estrogen receptor binding + 0.6651 66.51%
Androgen receptor binding - 0.5331 53.31%
Thyroid receptor binding + 0.5731 57.31%
Glucocorticoid receptor binding - 0.4692 46.92%
Aromatase binding - 0.7350 73.50%
PPAR gamma - 0.5971 59.71%
Honey bee toxicity - 0.7662 76.62%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.7000 70.00%
Fish aquatic toxicity + 0.9230 92.30%

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
CHEMBL4072 P07858 Cathepsin B 98.04% 93.67%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.49% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 95.93% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.71% 96.09%
CHEMBL2581 P07339 Cathepsin D 94.86% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.39% 95.56%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 86.49% 90.71%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.43% 93.56%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.24% 95.89%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 82.48% 91.11%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 82.35% 93.04%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 81.93% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.98% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.58% 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.
Zinnia angustifolia

Cross-Links

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PubChem 162847641
LOTUS LTS0271375
wikiData Q105121593