Michefucscalide

Details

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Internal ID ca8825be-7d23-435d-bc2a-72311f787d9d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4S,6aR,9S,9aS,9bS)-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] acetate
SMILES (Canonical) CC(=O)OC1CC(=C)C2CCC(C2C3C1C(=C)C(=O)O3)(C)O
SMILES (Isomeric) CC(=O)O[C@H]1CC(=C)[C@@H]2CC[C@]([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)(C)O
InChI InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h11-15,20H,1-2,5-7H2,3-4H3/t11-,12-,13+,14-,15-,17-/m0/s1
InChI Key BOGLHGTVFPSTPV-XSNIPSOOSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C17H22O5
Molecular Weight 306.40 g/mol
Exact Mass 306.14672380 g/mol
Topological Polar Surface Area (TPSA) 72.80 Ų
XlogP 1.40
Atomic LogP (AlogP) 1.75
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 1

Synonyms

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82461-08-3
[(3aR,4S,6aR,9S,9aS,9bS)-9-hydroxy-9-methyl-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] acetate
beta-Cyclolipiferolide
DTXSID401002693
9-Hydroxy-9-methyl-3,6-dimethylidene-2-oxododecahydroazuleno[4,5-b]furan-4-yl acetate
Azuleno(4,5-b)furan-2(3H)-one, 4-(acetyloxy)decahydro-9-hydroxy-9-methyl-3,6-bis(methylene)-, (3aR-(3aalpha,4alpha,6aalpha,9alpha,9aalpha,9bbeta))-

2D Structure

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2D Structure of Michefucscalide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9824 98.24%
Caco-2 + 0.5263 52.63%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.6819 68.19%
OATP2B1 inhibitior - 0.8568 85.68%
OATP1B1 inhibitior + 0.8812 88.12%
OATP1B3 inhibitior + 0.8756 87.56%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6842 68.42%
BSEP inhibitior - 0.9642 96.42%
P-glycoprotein inhibitior - 0.7738 77.38%
P-glycoprotein substrate - 0.7878 78.78%
CYP3A4 substrate + 0.6652 66.52%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8958 89.58%
CYP3A4 inhibition - 0.6763 67.63%
CYP2C9 inhibition - 0.7403 74.03%
CYP2C19 inhibition - 0.7576 75.76%
CYP2D6 inhibition - 0.9502 95.02%
CYP1A2 inhibition + 0.6310 63.10%
CYP2C8 inhibition - 0.7147 71.47%
CYP inhibitory promiscuity - 0.9576 95.76%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.6002 60.02%
Eye corrosion - 0.9827 98.27%
Eye irritation - 0.8021 80.21%
Skin irritation + 0.5197 51.97%
Skin corrosion - 0.8881 88.81%
Ames mutagenesis - 0.6300 63.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5864 58.64%
Micronuclear - 0.7600 76.00%
Hepatotoxicity + 0.7119 71.19%
skin sensitisation - 0.8024 80.24%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.8875 88.75%
Nephrotoxicity + 0.8644 86.44%
Acute Oral Toxicity (c) II 0.4822 48.22%
Estrogen receptor binding + 0.7456 74.56%
Androgen receptor binding + 0.6277 62.77%
Thyroid receptor binding + 0.5486 54.86%
Glucocorticoid receptor binding + 0.7069 70.69%
Aromatase binding - 0.5837 58.37%
PPAR gamma - 0.5574 55.74%
Honey bee toxicity - 0.7267 72.67%
Biodegradation - 0.6500 65.00%
Crustacea aquatic toxicity - 0.5050 50.50%
Fish aquatic toxicity + 0.9914 99.14%

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 96.62% 91.11%
CHEMBL2996 Q05655 Protein kinase C delta 91.92% 97.79%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.00% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 90.07% 85.14%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.24% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 86.10% 91.19%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.05% 96.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.47% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.20% 95.56%
CHEMBL2581 P07339 Cathepsin D 83.43% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.09% 97.09%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 82.91% 95.71%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.64% 97.25%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.73% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.67% 86.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.25% 92.94%

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.
Liriodendron tulipifera

Cross-Links

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PubChem 133912
LOTUS LTS0224026
wikiData Q82996931