methyl 2-[(1R,2S,4R,6R,9R,10R,11R,12S,15R,18S)-6-(furan-3-yl)-12-hydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-10-yl]acetate

Details

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Internal ID 9b6e23eb-845c-4ec5-a0b0-3877a7c6a28b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name methyl 2-[(1R,2S,4R,6R,9R,10R,11R,12S,15R,18S)-6-(furan-3-yl)-12-hydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-10-yl]acetate
SMILES (Canonical) CC1=C2C(CC1C3=COC=C3)OC4C2(C(C5(C(CCC6(C5C4OC6)C)O)C)CC(=O)OC)C
SMILES (Isomeric) CC1=C2[C@@H](C[C@H]1C3=COC=C3)O[C@H]4[C@@]2([C@@H]([C@]5([C@H](CC[C@@]6([C@@H]5[C@H]4OC6)C)O)C)CC(=O)OC)C
InChI InChI=1S/C27H36O6/c1-14-16(15-7-9-31-12-15)10-17-21(14)27(4)18(11-20(29)30-5)26(3)19(28)6-8-25(2)13-32-22(23(25)26)24(27)33-17/h7,9,12,16-19,22-24,28H,6,8,10-11,13H2,1-5H3/t16-,17-,18-,19+,22-,23+,24-,25+,26+,27-/m1/s1
InChI Key NAXSSFQPEXJWGN-FEEXMUEUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H36O6
Molecular Weight 456.60 g/mol
Exact Mass 456.25118886 g/mol
Topological Polar Surface Area (TPSA) 78.10 Ų
XlogP 2.60
Atomic LogP (AlogP) 4.23
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl 2-[(1R,2S,4R,6R,9R,10R,11R,12S,15R,18S)-6-(furan-3-yl)-12-hydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-10-yl]acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9945 99.45%
Caco-2 - 0.5765 57.65%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8565 85.65%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7358 73.58%
OATP1B3 inhibitior + 0.9222 92.22%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.9365 93.65%
P-glycoprotein inhibitior + 0.6466 64.66%
P-glycoprotein substrate + 0.6709 67.09%
CYP3A4 substrate + 0.7171 71.71%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8200 82.00%
CYP3A4 inhibition + 0.6233 62.33%
CYP2C9 inhibition - 0.6869 68.69%
CYP2C19 inhibition - 0.7581 75.81%
CYP2D6 inhibition - 0.9005 90.05%
CYP1A2 inhibition - 0.8248 82.48%
CYP2C8 inhibition + 0.8054 80.54%
CYP inhibitory promiscuity - 0.7056 70.56%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4860 48.60%
Eye corrosion - 0.9924 99.24%
Eye irritation - 0.9399 93.99%
Skin irritation - 0.5587 55.87%
Skin corrosion - 0.9524 95.24%
Ames mutagenesis - 0.6934 69.34%
Human Ether-a-go-go-Related Gene inhibition + 0.7979 79.79%
Micronuclear - 0.7200 72.00%
Hepatotoxicity + 0.5163 51.63%
skin sensitisation - 0.9148 91.48%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.6089 60.89%
Acute Oral Toxicity (c) I 0.4073 40.73%
Estrogen receptor binding + 0.8392 83.92%
Androgen receptor binding + 0.7199 71.99%
Thyroid receptor binding - 0.4921 49.21%
Glucocorticoid receptor binding + 0.8376 83.76%
Aromatase binding + 0.7543 75.43%
PPAR gamma + 0.7254 72.54%
Honey bee toxicity - 0.6936 69.36%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity + 0.6800 68.00%
Fish aquatic toxicity + 0.9921 99.21%

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 98.02% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 97.04% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 95.03% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.69% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.28% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.25% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.58% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.44% 85.14%
CHEMBL2243 O00519 Anandamide amidohydrolase 88.24% 97.53%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 87.45% 92.62%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.54% 95.56%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 84.81% 94.33%
CHEMBL226 P30542 Adenosine A1 receptor 84.08% 95.93%
CHEMBL5028 O14672 ADAM10 83.89% 97.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.86% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.34% 89.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.27% 100.00%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 83.21% 81.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.02% 97.14%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.38% 100.00%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.34% 93.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.63% 95.50%
CHEMBL4208 P20618 Proteasome component C5 80.44% 90.00%

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.
Azadirachta excelsa

Cross-Links

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PubChem 10718624
LOTUS LTS0026265
wikiData Q105176624