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[(3aS,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 3-methylbutanoate

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID f5f6e3bd-1343-4274-8497-ec8ce0e5e20e
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
IUPAC Name [(3aS,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 3-methylbutanoate
SMILES (Canonical) CC(C)CC(=O)OC1C2C(CC(C=CC(=O)C(C1OC(=O)C)(C)O)CO)OC(=O)C2=C
SMILES (Isomeric) CC(C)CC(=O)O[C@H]1[C@@H]2[C@@H](C[C@H](/C=C\C(=O)[C@]([C@@H]1OC(=O)C)(C)O)CO)OC(=O)C2=C
InChI InChI=1S/C22H30O9/c1-11(2)8-17(26)31-19-18-12(3)21(27)30-15(18)9-14(10-23)6-7-16(25)22(5,28)20(19)29-13(4)24/h6-7,11,14-15,18-20,23,28H,3,8-10H2,1-2,4-5H3/b7-6-/t14-,15+,18-,19-,20+,22-/m0/s1
InChI Key QPBUKUPRAWUHCJ-NWYNSBMJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H30O9
Molecular Weight 438.50 g/mol
Exact Mass 438.18898253 g/mol
Topological Polar Surface Area (TPSA) 136.00 Ų
XlogP 1.20
Atomic LogP (AlogP) 0.86
H-Bond Acceptor 9
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,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-10-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] 3-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9720 97.20%
Caco-2 - 0.6134 61.34%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7296 72.96%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8287 82.87%
OATP1B3 inhibitior + 0.8769 87.69%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.4923 49.23%
P-glycoprotein inhibitior + 0.6618 66.18%
P-glycoprotein substrate + 0.5218 52.18%
CYP3A4 substrate + 0.6483 64.83%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9136 91.36%
CYP3A4 inhibition - 0.7873 78.73%
CYP2C9 inhibition - 0.7469 74.69%
CYP2C19 inhibition - 0.8246 82.46%
CYP2D6 inhibition - 0.9355 93.55%
CYP1A2 inhibition - 0.7750 77.50%
CYP2C8 inhibition - 0.6596 65.96%
CYP inhibitory promiscuity - 0.8415 84.15%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9143 91.43%
Carcinogenicity (trinary) Non-required 0.5400 54.00%
Eye corrosion - 0.9751 97.51%
Eye irritation - 0.9339 93.39%
Skin irritation - 0.7132 71.32%
Skin corrosion - 0.9300 93.00%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5208 52.08%
Micronuclear - 0.7000 70.00%
Hepatotoxicity + 0.7000 70.00%
skin sensitisation - 0.7118 71.18%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity + 0.7638 76.38%
Acute Oral Toxicity (c) III 0.4924 49.24%
Estrogen receptor binding + 0.6905 69.05%
Androgen receptor binding + 0.5622 56.22%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.7846 78.46%
Aromatase binding + 0.6202 62.02%
PPAR gamma + 0.5530 55.30%
Honey bee toxicity - 0.6978 69.78%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.9229 92.29%

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
CHEMBL2996 Q05655 Protein kinase C delta 98.37% 97.79%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.14% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.37% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.26% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.07% 97.25%
CHEMBL299 P17252 Protein kinase C alpha 94.36% 98.03%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.24% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.10% 95.56%
CHEMBL2581 P07339 Cathepsin D 91.04% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.74% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.92% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 87.36% 97.14%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 86.01% 95.50%
CHEMBL340 P08684 Cytochrome P450 3A4 85.84% 91.19%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.66% 91.07%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.81% 89.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 82.22% 89.50%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 81.19% 82.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.63% 99.23%
CHEMBL5028 O14672 ADAM10 80.27% 97.50%

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.
Neurolaena lobata

Cross-Links

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PubChem 101921668
LOTUS LTS0237444
wikiData Q105225298