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(5Z)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.02,6.03,9]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one

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 11e9a8d8-0574-42ac-b4d9-45ec68c1bf5c
Taxonomy Organoheterocyclic compounds > Pyrrolizidines
IUPAC Name (5Z)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.02,6.03,9]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one
SMILES (Canonical) CCCCC12C3CCN1C4CC2OC3(C4C(C)C=C5C(=C(C(=O)O5)C)OC)O
SMILES (Isomeric) CCCC[C@@]12[C@H]3CCN1[C@H]4C[C@@H]2O[C@@]3([C@@H]4[C@H](C)/C=C\5/C(=C(C(=O)O5)C)OC)O
InChI InChI=1S/C22H31NO5/c1-5-6-8-21-16-7-9-23(21)14-11-17(21)28-22(16,25)18(14)12(2)10-15-19(26-4)13(3)20(24)27-15/h10,12,14,16-18,25H,5-9,11H2,1-4H3/b15-10-/t12-,14+,16-,17+,18-,21+,22+/m1/s1
InChI Key LLRUDQNWYFSTOW-JBRPLHHRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H31NO5
Molecular Weight 389.50 g/mol
Exact Mass 389.22022309 g/mol
Topological Polar Surface Area (TPSA) 68.20 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.72
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (5Z)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.02,6.03,9]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-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 + 0.8794 87.94%
Caco-2 + 0.5579 55.79%
Blood Brain Barrier + 0.7750 77.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.5206 52.06%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8621 86.21%
OATP1B3 inhibitior + 0.9204 92.04%
MATE1 inhibitior - 0.8409 84.09%
OCT2 inhibitior - 0.6250 62.50%
BSEP inhibitior + 0.9157 91.57%
P-glycoprotein inhibitior - 0.5137 51.37%
P-glycoprotein substrate + 0.6250 62.50%
CYP3A4 substrate + 0.6865 68.65%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8111 81.11%
CYP3A4 inhibition - 0.9557 95.57%
CYP2C9 inhibition - 0.8925 89.25%
CYP2C19 inhibition - 0.9253 92.53%
CYP2D6 inhibition - 0.8984 89.84%
CYP1A2 inhibition - 0.8858 88.58%
CYP2C8 inhibition - 0.6417 64.17%
CYP inhibitory promiscuity - 0.8212 82.12%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4727 47.27%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9821 98.21%
Skin irritation - 0.7301 73.01%
Skin corrosion - 0.9284 92.84%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4278 42.78%
Micronuclear + 0.5300 53.00%
Hepatotoxicity - 0.6102 61.02%
skin sensitisation - 0.8629 86.29%
Respiratory toxicity + 0.7556 75.56%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity + 0.9000 90.00%
Nephrotoxicity + 0.5228 52.28%
Acute Oral Toxicity (c) III 0.6282 62.82%
Estrogen receptor binding + 0.8146 81.46%
Androgen receptor binding + 0.6581 65.81%
Thyroid receptor binding + 0.6852 68.52%
Glucocorticoid receptor binding + 0.6450 64.50%
Aromatase binding + 0.6292 62.92%
PPAR gamma + 0.5722 57.22%
Honey bee toxicity - 0.8567 85.67%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9011 90.11%

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
CHEMBL2581 P07339 Cathepsin D 96.82% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.78% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.99% 97.25%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 92.70% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.26% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.01% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.75% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.06% 94.45%
CHEMBL4072 P07858 Cathepsin B 89.93% 93.67%
CHEMBL221 P23219 Cyclooxygenase-1 89.26% 90.17%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 88.93% 92.86%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 87.99% 90.24%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 87.01% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.17% 99.23%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 86.01% 96.47%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.54% 93.00%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 85.05% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.01% 95.89%
CHEMBL4588 P22894 Matrix metalloproteinase 8 84.70% 94.66%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.62% 86.33%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 83.19% 95.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.17% 92.62%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.11% 97.14%
CHEMBL3359 P21462 Formyl peptide receptor 1 82.97% 93.56%
CHEMBL4835 P00338 L-lactate dehydrogenase A chain 82.94% 95.34%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 82.01% 91.03%
CHEMBL6136 O60341 Lysine-specific histone demethylase 1 81.07% 95.58%
CHEMBL218 P21554 Cannabinoid CB1 receptor 80.51% 96.61%
CHEMBL1795139 Q8IU80 Transmembrane protease serine 6 80.39% 98.33%

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.
Stemona burkillii

Cross-Links

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PubChem 102286592
LOTUS LTS0068707
wikiData Q105153692