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[(1S,2R,5S,6S,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-acetyloxy-6-(furan-3-yl)-12,19,21-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 09e96aec-0799-4e98-a76f-93cd8e01efb7
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name [(1S,2R,5S,6S,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-acetyloxy-6-(furan-3-yl)-12,19,21-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(C(C2O)OC(=O)C)O)C(=O)CC5(C46C(O6)CC5C7=COC=C7)C)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@H]([C@H]2O)OC(=O)C)O)C(=O)C[C@@]5([C@]46[C@H](O6)C[C@H]5C7=COC=C7)C)C)O)C
InChI InChI=1S/C33H44O11/c1-7-15(2)27(39)43-28-30(5)20-11-21(36)31(6)24(32(20,14-41-28)26(38)23(25(30)37)42-16(3)34)19(35)12-29(4)18(17-8-9-40-13-17)10-22-33(29,31)44-22/h8-9,13,15,18,20-26,28,36-38H,7,10-12,14H2,1-6H3/t15-,18+,20+,21-,22-,23+,24+,25-,26+,28-,29+,30-,31-,32+,33-/m1/s1
InChI Key GXRJHIFVOGNSHF-NFVPAXSTSA-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 1.70
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,5S,6S,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-acetyloxy-6-(furan-3-yl)-12,19,21-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 + 0.9417 94.17%
Caco-2 - 0.8203 82.03%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.7016 70.16%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.6876 68.76%
OATP1B3 inhibitior + 0.8833 88.33%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8364 83.64%
BSEP inhibitior + 0.9426 94.26%
P-glycoprotein inhibitior + 0.7384 73.84%
P-glycoprotein substrate + 0.6785 67.85%
CYP3A4 substrate + 0.7184 71.84%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8322 83.22%
CYP3A4 inhibition + 0.6655 66.55%
CYP2C9 inhibition - 0.8104 81.04%
CYP2C19 inhibition - 0.8650 86.50%
CYP2D6 inhibition - 0.9446 94.46%
CYP1A2 inhibition - 0.9020 90.20%
CYP2C8 inhibition + 0.6596 65.96%
CYP inhibitory promiscuity - 0.8121 81.21%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6140 61.40%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9145 91.45%
Skin irritation - 0.7047 70.47%
Skin corrosion - 0.9416 94.16%
Ames mutagenesis - 0.5555 55.55%
Human Ether-a-go-go-Related Gene inhibition + 0.7292 72.92%
Micronuclear - 0.5800 58.00%
Hepatotoxicity + 0.5500 55.00%
skin sensitisation - 0.8958 89.58%
Respiratory toxicity + 0.8111 81.11%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.4582 45.82%
Acute Oral Toxicity (c) I 0.5307 53.07%
Estrogen receptor binding + 0.8039 80.39%
Androgen receptor binding + 0.7591 75.91%
Thyroid receptor binding + 0.5405 54.05%
Glucocorticoid receptor binding + 0.7414 74.14%
Aromatase binding + 0.7086 70.86%
PPAR gamma + 0.7408 74.08%
Honey bee toxicity - 0.7337 73.37%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5300 53.00%
Fish aquatic toxicity + 0.9879 98.79%

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 98.80% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.59% 96.09%
CHEMBL2581 P07339 Cathepsin D 96.56% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.99% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.31% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.18% 97.09%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 92.51% 96.77%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.93% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.64% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.53% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 89.24% 90.17%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.99% 94.00%
CHEMBL3922 P50579 Methionine aminopeptidase 2 87.75% 97.28%
CHEMBL340 P08684 Cytochrome P450 3A4 87.33% 91.19%
CHEMBL4051 P13569 Cystic fibrosis transmembrane conductance regulator 85.07% 95.71%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.43% 92.62%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 84.07% 82.69%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 83.67% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.02% 93.00%
CHEMBL2996 Q05655 Protein kinase C delta 82.70% 97.79%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.50% 99.23%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.38% 85.14%

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 163185322
LOTUS LTS0017326
wikiData Q105023309