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[(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-21-acetyloxy-6-(furan-3-yl)-4,12,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate

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 e07071e1-3168-4d06-ae44-d3829393979d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name [(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-21-acetyloxy-6-(furan-3-yl)-4,12,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate
SMILES (Canonical) CCC(C)C(=O)OC1C2(C3CC(C4(C(C3(CO1)C(CC2OC(=O)C)O)C(=O)C(C5(C46C(O6)CC5C7=COC=C7)C)O)C)O)C
SMILES (Isomeric) CC[C@@H](C)C(=O)O[C@H]1[C@@]2([C@@H]3C[C@H]([C@@]4([C@@H]([C@@]3(CO1)[C@H](C[C@H]2OC(=O)C)O)C(=O)[C@@H]([C@@]5([C@]46[C@H](O6)C[C@H]5C7=COC=C7)C)O)C)O)C
InChI InChI=1S/C33H44O11/c1-7-15(2)27(39)43-28-29(4)19-11-20(35)31(6)25(32(19,14-41-28)21(36)12-22(29)42-16(3)34)24(37)26(38)30(5)18(17-8-9-40-13-17)10-23-33(30,31)44-23/h8-9,13,15,18-23,25-26,28,35-36,38H,7,10-12,14H2,1-6H3/t15-,18+,19+,20-,21+,22-,23-,25+,26+,28+,29-,30-,31-,32-,33-/m1/s1
InChI Key GFWAUGVHDIJBDI-NZEBTISYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C33H44O11
Molecular Weight 616.70 g/mol
Exact Mass 616.28836222 g/mol
Topological Polar Surface Area (TPSA) 165.00 Ų
XlogP 2.10
Atomic LogP (AlogP) 2.49
H-Bond Acceptor 11
H-Bond Donor 3
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2R,4R,5R,6S,8R,10S,11S,12R,14R,15R,16S,19S,21R)-21-acetyloxy-6-(furan-3-yl)-4,12,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-16-yl] (2R)-2-methylbutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9734 97.34%
Caco-2 - 0.8102 81.02%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.7591 75.91%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior - 0.3217 32.17%
OATP1B3 inhibitior + 0.8015 80.15%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8614 86.14%
BSEP inhibitior + 0.9379 93.79%
P-glycoprotein inhibitior + 0.7234 72.34%
P-glycoprotein substrate + 0.6786 67.86%
CYP3A4 substrate + 0.7082 70.82%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8322 83.22%
CYP3A4 inhibition + 0.6928 69.28%
CYP2C9 inhibition - 0.7843 78.43%
CYP2C19 inhibition - 0.8404 84.04%
CYP2D6 inhibition - 0.9504 95.04%
CYP1A2 inhibition - 0.8795 87.95%
CYP2C8 inhibition + 0.6882 68.82%
CYP inhibitory promiscuity - 0.8322 83.22%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5800 58.00%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9152 91.52%
Skin irritation - 0.6998 69.98%
Skin corrosion - 0.9447 94.47%
Ames mutagenesis - 0.5701 57.01%
Human Ether-a-go-go-Related Gene inhibition + 0.7427 74.27%
Micronuclear - 0.5800 58.00%
Hepatotoxicity + 0.6626 66.26%
skin sensitisation - 0.8993 89.93%
Respiratory toxicity + 0.7778 77.78%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity + 0.4934 49.34%
Acute Oral Toxicity (c) I 0.5420 54.20%
Estrogen receptor binding + 0.7997 79.97%
Androgen receptor binding + 0.7562 75.62%
Thyroid receptor binding + 0.5389 53.89%
Glucocorticoid receptor binding + 0.7763 77.63%
Aromatase binding + 0.7028 70.28%
PPAR gamma + 0.7415 74.15%
Honey bee toxicity - 0.7016 70.16%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9904 99.04%

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
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 98.37% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.98% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.77% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.57% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 94.69% 90.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.12% 97.09%
CHEMBL3922 P50579 Methionine aminopeptidase 2 91.65% 97.28%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.47% 97.25%
CHEMBL4040 P28482 MAP kinase ERK2 91.01% 83.82%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.14% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.42% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.36% 86.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.50% 92.62%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 85.68% 95.71%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 85.55% 85.14%
CHEMBL340 P08684 Cytochrome P450 3A4 85.37% 91.19%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.96% 94.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.67% 96.00%
CHEMBL2996 Q05655 Protein kinase C delta 82.54% 97.79%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.25% 89.50%
CHEMBL3145 P42338 PI3-kinase p110-beta subunit 80.69% 98.75%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.54% 100.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.20% 99.23%

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 162976936
LOTUS LTS0176050
wikiData Q105007833