[(3R,3aR,4R,9aS,9bR)-6-(hydroxymethyl)-3,9-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate

Details

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Internal ID b9d8be8f-f38b-48d4-9996-e81582454800
Taxonomy Lipids and lipid-like molecules > Fatty Acyls > Fatty acid esters
IUPAC Name [(3R,3aR,4R,9aS,9bR)-6-(hydroxymethyl)-3,9-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(=C2C(C3C1C(C(=O)O3)C)C(=CC2=O)C)CO
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@@H]1CC(=C2[C@@H]([C@@H]3[C@@H]1[C@H](C(=O)O3)C)C(=CC2=O)C)CO
InChI InChI=1S/C20H24O6/c1-5-9(2)19(23)25-14-7-12(8-21)17-13(22)6-10(3)15(17)18-16(14)11(4)20(24)26-18/h5-6,11,14-16,18,21H,7-8H2,1-4H3/b9-5+/t11-,14-,15+,16-,18-/m1/s1
InChI Key MPSLOJNTSSQWHP-NKSQJKDXSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H24O6
Molecular Weight 360.40 g/mol
Exact Mass 360.15728848 g/mol
Topological Polar Surface Area (TPSA) 89.90 Ų
XlogP 1.20
Atomic LogP (AlogP) 1.88
H-Bond Acceptor 6
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 [(3R,3aR,4R,9aS,9bR)-6-(hydroxymethyl)-3,9-dimethyl-2,7-dioxo-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] (E)-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 + 0.9872 98.72%
Caco-2 + 0.7883 78.83%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7126 71.26%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8794 87.94%
OATP1B3 inhibitior + 0.9191 91.91%
MATE1 inhibitior - 0.7812 78.12%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior - 0.5192 51.92%
P-glycoprotein inhibitior - 0.5796 57.96%
P-glycoprotein substrate - 0.6086 60.86%
CYP3A4 substrate + 0.6148 61.48%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9063 90.63%
CYP3A4 inhibition - 0.7650 76.50%
CYP2C9 inhibition - 0.7795 77.95%
CYP2C19 inhibition - 0.8489 84.89%
CYP2D6 inhibition - 0.9492 94.92%
CYP1A2 inhibition - 0.6031 60.31%
CYP2C8 inhibition - 0.7318 73.18%
CYP inhibitory promiscuity - 0.8338 83.38%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9343 93.43%
Carcinogenicity (trinary) Non-required 0.5752 57.52%
Eye corrosion - 0.9656 96.56%
Eye irritation - 0.9309 93.09%
Skin irritation - 0.6849 68.49%
Skin corrosion - 0.9343 93.43%
Ames mutagenesis + 0.5818 58.18%
Human Ether-a-go-go-Related Gene inhibition + 0.6778 67.78%
Micronuclear - 0.6100 61.00%
Hepatotoxicity + 0.6245 62.45%
skin sensitisation - 0.7954 79.54%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity + 0.5567 55.67%
Acute Oral Toxicity (c) III 0.4686 46.86%
Estrogen receptor binding + 0.6872 68.72%
Androgen receptor binding + 0.6458 64.58%
Thyroid receptor binding - 0.5526 55.26%
Glucocorticoid receptor binding + 0.6472 64.72%
Aromatase binding - 0.7950 79.50%
PPAR gamma + 0.5527 55.27%
Honey bee toxicity - 0.7535 75.35%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.7744 77.44%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.92% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.34% 96.09%
CHEMBL2581 P07339 Cathepsin D 90.23% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.07% 94.45%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 88.63% 94.80%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.47% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.13% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.42% 97.25%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.88% 99.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.54% 99.23%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.54% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.50% 97.09%

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.
Eupatorium perfoliatum
Hunteria zeylanica
Pseudognaphalium affine
Vernonia pachyclada

Cross-Links

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PubChem 101794216
NPASS NPC146566
LOTUS LTS0188860
wikiData Q105169714