[6-(Hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3a,4,5,6,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 4-acetyloxy-2-methylbut-2-enoate

Details

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Internal ID db50e001-eb01-4ab5-92ad-24fbe4fef201
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [6-(hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3a,4,5,6,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 4-acetyloxy-2-methylbut-2-enoate
SMILES (Canonical) CC1=CCC2C1C3C(C(CC2CO)OC(=O)C(=CCOC(=O)C)C)C(=C)C(=O)O3
SMILES (Isomeric) CC1=CCC2C1C3C(C(CC2CO)OC(=O)C(=CCOC(=O)C)C)C(=C)C(=O)O3
InChI InChI=1S/C22H28O7/c1-11-5-6-16-15(10-23)9-17(19-13(3)22(26)29-20(19)18(11)16)28-21(25)12(2)7-8-27-14(4)24/h5,7,15-20,23H,3,6,8-10H2,1-2,4H3
InChI Key NBAVQZMELBZDQW-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H28O7
Molecular Weight 404.50 g/mol
Exact Mass 404.18350323 g/mol
Topological Polar Surface Area (TPSA) 99.10 Ų
XlogP 1.90
Atomic LogP (AlogP) 2.10
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [6-(Hydroxymethyl)-9-methyl-3-methylidene-2-oxo-3a,4,5,6,6a,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 4-acetyloxy-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 + 0.9597 95.97%
Caco-2 - 0.6013 60.13%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.6556 65.56%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8922 89.22%
OATP1B3 inhibitior + 0.9442 94.42%
MATE1 inhibitior - 0.8212 82.12%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.6715 67.15%
P-glycoprotein inhibitior + 0.5752 57.52%
P-glycoprotein substrate - 0.6636 66.36%
CYP3A4 substrate + 0.6390 63.90%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9071 90.71%
CYP3A4 inhibition - 0.5582 55.82%
CYP2C9 inhibition - 0.7911 79.11%
CYP2C19 inhibition - 0.7494 74.94%
CYP2D6 inhibition - 0.9396 93.96%
CYP1A2 inhibition - 0.6564 65.64%
CYP2C8 inhibition - 0.6430 64.30%
CYP inhibitory promiscuity - 0.8508 85.08%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6615 66.15%
Eye corrosion - 0.9737 97.37%
Eye irritation - 0.8796 87.96%
Skin irritation - 0.6674 66.74%
Skin corrosion - 0.9265 92.65%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4941 49.41%
Micronuclear - 0.7800 78.00%
Hepatotoxicity + 0.6803 68.03%
skin sensitisation - 0.8105 81.05%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.6444 64.44%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity + 0.7594 75.94%
Acute Oral Toxicity (c) III 0.4159 41.59%
Estrogen receptor binding + 0.7867 78.67%
Androgen receptor binding + 0.6523 65.23%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.6540 65.40%
Aromatase binding - 0.6613 66.13%
PPAR gamma + 0.6245 62.45%
Honey bee toxicity - 0.7113 71.13%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9650 96.50%

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 93.10% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.82% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.50% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.69% 94.45%
CHEMBL3401 O75469 Pregnane X receptor 88.26% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.61% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 87.09% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.28% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.91% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.26% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.15% 99.17%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.96% 95.50%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.88% 97.25%

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.
Stevia breviaristata

Cross-Links

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PubChem 162897150
LOTUS LTS0090986
wikiData Q105176682