methyl (1S,4S,5R,6S,7S,8R,11S,12R,14R,15S)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-(3-methylbutanoyloxy)-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-11-carboxylate

Details

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Internal ID 6650edf5-a457-42df-9d68-242efde16db0
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name methyl (1S,4S,5R,6S,7S,8R,11S,12R,14R,15S)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-(3-methylbutanoyloxy)-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-11-carboxylate
SMILES (Canonical) CC(C)CC(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)O)C(=O)OC)OC(=O)C
SMILES (Isomeric) CC(C)CC(=O)O[C@@H]1C[C@H]([C@]2(CO[C@@H]3[C@H]2[C@]14CO[C@@H]([C@H]4[C@]([C@@H]3O)(C)[C@@]56[C@@H]7C[C@H]([C@@]5(O6)C)[C@@]8(C=CO[C@H]8O7)O)O)C(=O)OC)OC(=O)C
InChI InChI=1S/C33H44O14/c1-14(2)9-20(35)45-17-11-18(44-15(3)34)31(26(38)40-6)13-42-21-22(31)30(17)12-43-25(37)23(30)28(4,24(21)36)33-19-10-16(29(33,5)47-33)32(39)7-8-41-27(32)46-19/h7-8,14,16-19,21-25,27,36-37,39H,9-13H2,1-6H3/t16-,17-,18-,19+,21-,22+,23+,24-,25+,27+,28+,29+,30+,31+,32-,33+/m1/s1
InChI Key OLVMXZKTRMVIJY-LEXJWOSASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C33H44O14
Molecular Weight 664.70 g/mol
Exact Mass 664.27310607 g/mol
Topological Polar Surface Area (TPSA) 189.00 Ų
XlogP -0.30
Atomic LogP (AlogP) 0.33
H-Bond Acceptor 14
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,4S,5R,6S,7S,8R,11S,12R,14R,15S)-12-acetyloxy-4,7-dihydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-(3-methylbutanoyloxy)-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-11-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9282 92.82%
Caco-2 - 0.8412 84.12%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.7896 78.96%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8093 80.93%
OATP1B3 inhibitior + 0.8665 86.65%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8768 87.68%
P-glycoprotein inhibitior + 0.7100 71.00%
P-glycoprotein substrate + 0.7309 73.09%
CYP3A4 substrate + 0.7303 73.03%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8693 86.93%
CYP3A4 inhibition - 0.7278 72.78%
CYP2C9 inhibition - 0.7619 76.19%
CYP2C19 inhibition - 0.7890 78.90%
CYP2D6 inhibition - 0.9412 94.12%
CYP1A2 inhibition - 0.9122 91.22%
CYP2C8 inhibition + 0.7113 71.13%
CYP inhibitory promiscuity - 0.8739 87.39%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5885 58.85%
Eye corrosion - 0.9865 98.65%
Eye irritation - 0.9137 91.37%
Skin irritation - 0.7490 74.90%
Skin corrosion - 0.9397 93.97%
Ames mutagenesis + 0.6200 62.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5480 54.80%
Micronuclear - 0.6200 62.00%
Hepatotoxicity - 0.6390 63.90%
skin sensitisation - 0.8605 86.05%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity + 0.4585 45.85%
Acute Oral Toxicity (c) I 0.7222 72.22%
Estrogen receptor binding + 0.7662 76.62%
Androgen receptor binding + 0.7518 75.18%
Thyroid receptor binding + 0.5147 51.47%
Glucocorticoid receptor binding + 0.6789 67.89%
Aromatase binding + 0.7072 70.72%
PPAR gamma + 0.7370 73.70%
Honey bee toxicity - 0.8910 89.10%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9842 98.42%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.14% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.90% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.52% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.29% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.35% 89.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 90.59% 89.50%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 90.54% 92.62%
CHEMBL2581 P07339 Cathepsin D 90.26% 98.95%
CHEMBL253 P34972 Cannabinoid CB2 receptor 89.09% 97.25%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 88.63% 91.07%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 86.90% 95.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.16% 97.09%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 84.75% 97.14%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 84.68% 96.47%
CHEMBL340 P08684 Cytochrome P450 3A4 84.56% 91.19%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.94% 99.17%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 82.96% 82.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.95% 96.00%
CHEMBL1914 P06276 Butyrylcholinesterase 80.97% 95.00%
CHEMBL3401 O75469 Pregnane X receptor 80.76% 94.73%
CHEMBL3776 Q14790 Caspase-8 80.55% 97.06%
CHEMBL5028 O14672 ADAM10 80.37% 97.50%
CHEMBL221 P23219 Cyclooxygenase-1 80.36% 90.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.35% 95.89%

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.
Azadirachta excelsa

Cross-Links

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PubChem 163028330
LOTUS LTS0095023
wikiData Q105194161