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[(1R,4R,5R,7S,8R,9R,10R,11S,12R)-10-[(3R,5S)-5-acetyloxy-3-(furan-3-yl)-2-methylcyclopenten-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-7,11-bis[[(E)-2-methylbut-2-enoyl]oxy]-2-oxatricyclo[6.3.1.04,12]dodecan-5-yl] (E)-2-methylbut-2-enoate

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 5ac3fc43-b661-48ae-b22b-32cb7843ae13
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name [(1R,4R,5R,7S,8R,9R,10R,11S,12R)-10-[(3R,5S)-5-acetyloxy-3-(furan-3-yl)-2-methylcyclopenten-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-7,11-bis[[(E)-2-methylbut-2-enoyl]oxy]-2-oxatricyclo[6.3.1.04,12]dodecan-5-yl] (E)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(C2(C(C(C(C3C2C1(CO3)C)OC(=O)C(=CC)C)(C)C4=C(C(CC4OC(=O)C)C5=COC=C5)C)CC(=O)OC)C)OC(=O)C(=CC)C
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@@H]1C[C@@H]([C@@]2([C@H]([C@]([C@@H]([C@H]3[C@H]2[C@@]1(CO3)C)OC(=O)/C(=C/C)/C)(C)C4=C([C@@H](C[C@@H]4OC(=O)C)C5=COC=C5)C)CC(=O)OC)C)OC(=O)/C(=C/C)/C
InChI InChI=1S/C44H58O12/c1-13-23(4)39(47)54-32-20-33(55-40(48)24(5)14-2)43(10)31(19-34(46)50-12)44(11,35-26(7)29(28-16-17-51-21-28)18-30(35)53-27(8)45)38(56-41(49)25(6)15-3)36-37(43)42(32,9)22-52-36/h13-17,21,29-33,36-38H,18-20,22H2,1-12H3/b23-13+,24-14+,25-15+/t29-,30+,31-,32-,33+,36-,37+,38-,42-,43+,44-/m1/s1
InChI Key QCFBMZLALFSLDU-BRTRSVSESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C44H58O12
Molecular Weight 778.90 g/mol
Exact Mass 778.39282728 g/mol
Topological Polar Surface Area (TPSA) 154.00 Ų
XlogP 6.50
Atomic LogP (AlogP) 7.28
H-Bond Acceptor 12
H-Bond Donor 0
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1R,4R,5R,7S,8R,9R,10R,11S,12R)-10-[(3R,5S)-5-acetyloxy-3-(furan-3-yl)-2-methylcyclopenten-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-7,11-bis[[(E)-2-methylbut-2-enoyl]oxy]-2-oxatricyclo[6.3.1.04,12]dodecan-5-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 + 0.9949 99.49%
Caco-2 - 0.8199 81.99%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.7752 77.52%
OATP2B1 inhibitior - 0.5671 56.71%
OATP1B1 inhibitior + 0.7060 70.60%
OATP1B3 inhibitior + 0.8848 88.48%
MATE1 inhibitior - 0.6800 68.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 1.0000 100.00%
P-glycoprotein inhibitior + 0.8750 87.50%
P-glycoprotein substrate + 0.7262 72.62%
CYP3A4 substrate + 0.7139 71.39%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8924 89.24%
CYP3A4 inhibition + 0.5594 55.94%
CYP2C9 inhibition - 0.7959 79.59%
CYP2C19 inhibition - 0.8235 82.35%
CYP2D6 inhibition - 0.9542 95.42%
CYP1A2 inhibition - 0.8713 87.13%
CYP2C8 inhibition + 0.8547 85.47%
CYP inhibitory promiscuity + 0.5000 50.00%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4882 48.82%
Eye corrosion - 0.9895 98.95%
Eye irritation - 0.9028 90.28%
Skin irritation - 0.7338 73.38%
Skin corrosion - 0.9615 96.15%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7681 76.81%
Micronuclear - 0.5300 53.00%
Hepatotoxicity + 0.5677 56.77%
skin sensitisation - 0.8297 82.97%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity + 0.5929 59.29%
Acute Oral Toxicity (c) I 0.5096 50.96%
Estrogen receptor binding + 0.8031 80.31%
Androgen receptor binding + 0.7202 72.02%
Thyroid receptor binding + 0.6015 60.15%
Glucocorticoid receptor binding + 0.8139 81.39%
Aromatase binding + 0.6486 64.86%
PPAR gamma + 0.7907 79.07%
Honey bee toxicity - 0.6281 62.81%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity + 0.9974 99.74%

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 98.76% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.20% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.26% 86.33%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 91.76% 81.11%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 91.37% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.76% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 90.69% 90.17%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 90.49% 87.67%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.83% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.83% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.89% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.55% 94.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 86.98% 93.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.32% 92.62%
CHEMBL2581 P07339 Cathepsin D 85.85% 98.95%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 85.22% 94.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.27% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 82.54% 85.14%
CHEMBL2243 O00519 Anandamide amidohydrolase 82.18% 97.53%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.74% 100.00%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.04% 97.14%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.34% 91.24%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.34% 100.00%

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.
Melia azedarach

Cross-Links

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PubChem 101690767
LOTUS LTS0149626
wikiData Q105218202