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[(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-14-hydroxy-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-12-yl] (Z)-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 0cb76e54-1f70-4965-8658-d0cd16726cb8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name [(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-14-hydroxy-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-12-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(C2(COC3C2C1(C(C4(C3OC5C4=C(C(C5)C6=COC=C6)C)C)CC(=O)OC)C)C)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1C[C@H]([C@]2(CO[C@@H]3[C@@H]2[C@]1([C@H]([C@]4([C@@H]3O[C@H]5C4=C([C@@H](C5)C6=COC=C6)C)C)CC(=O)OC)C)C)O
InChI InChI=1S/C32H42O8/c1-8-16(2)29(35)40-23-13-22(33)30(4)15-38-26-27(30)31(23,5)21(12-24(34)36-7)32(6)25-17(3)19(18-9-10-37-14-18)11-20(25)39-28(26)32/h8-10,14,19-23,26-28,33H,11-13,15H2,1-7H3/b16-8-/t19-,20-,21-,22-,23+,26-,27+,28-,30-,31+,32-/m1/s1
InChI Key MJNRBOGIPLCVIM-JLDAJYGSSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C32H42O8
Molecular Weight 554.70 g/mol
Exact Mass 554.28796829 g/mol
Topological Polar Surface Area (TPSA) 104.00 Ų
XlogP 3.40
Atomic LogP (AlogP) 4.72
H-Bond Acceptor 8
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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CHEMBL1774413

2D Structure

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2D Structure of [(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-14-hydroxy-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.02,9.04,8.015,18]octadec-7-en-12-yl] (Z)-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 + 0.9963 99.63%
Caco-2 - 0.6894 68.94%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8001 80.01%
OATP2B1 inhibitior - 0.8601 86.01%
OATP1B1 inhibitior + 0.7259 72.59%
OATP1B3 inhibitior + 0.8986 89.86%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8114 81.14%
BSEP inhibitior + 0.9945 99.45%
P-glycoprotein inhibitior + 0.7868 78.68%
P-glycoprotein substrate + 0.7249 72.49%
CYP3A4 substrate + 0.7196 71.96%
CYP2C9 substrate - 0.7958 79.58%
CYP2D6 substrate - 0.8820 88.20%
CYP3A4 inhibition + 0.5710 57.10%
CYP2C9 inhibition - 0.7269 72.69%
CYP2C19 inhibition - 0.8919 89.19%
CYP2D6 inhibition - 0.9574 95.74%
CYP1A2 inhibition - 0.9007 90.07%
CYP2C8 inhibition + 0.8199 81.99%
CYP inhibitory promiscuity - 0.8472 84.72%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.4484 44.84%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9141 91.41%
Skin irritation - 0.6344 63.44%
Skin corrosion - 0.9524 95.24%
Ames mutagenesis - 0.5864 58.64%
Human Ether-a-go-go-Related Gene inhibition + 0.8215 82.15%
Micronuclear - 0.5400 54.00%
Hepatotoxicity + 0.5968 59.68%
skin sensitisation - 0.8690 86.90%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9556 95.56%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.5583 55.83%
Acute Oral Toxicity (c) I 0.6495 64.95%
Estrogen receptor binding + 0.8217 82.17%
Androgen receptor binding + 0.7146 71.46%
Thyroid receptor binding + 0.5510 55.10%
Glucocorticoid receptor binding + 0.8406 84.06%
Aromatase binding + 0.7113 71.13%
PPAR gamma + 0.7720 77.20%
Honey bee toxicity - 0.6200 62.00%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.6600 66.00%
Fish aquatic toxicity + 0.9952 99.52%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 33 nM
 Kd
 via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.38% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.80% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.78% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.65% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.37% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 91.63% 90.17%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.55% 94.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.11% 96.00%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 89.36% 81.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.36% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.85% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.65% 95.50%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.88% 85.14%
CHEMBL2243 O00519 Anandamide amidohydrolase 87.01% 97.53%
CHEMBL1293294 P51151 Ras-related protein Rab-9A 86.84% 87.67%
CHEMBL5028 O14672 ADAM10 86.45% 97.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.29% 99.17%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.35% 92.62%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.01% 93.00%
CHEMBL3401 O75469 Pregnane X receptor 84.35% 94.73%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 84.34% 89.67%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 82.72% 89.44%
CHEMBL3492 P49721 Proteasome Macropain subunit 82.31% 90.24%
CHEMBL2581 P07339 Cathepsin D 81.73% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.39% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.28% 94.33%

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 indica

Cross-Links

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PubChem 54583361
LOTUS LTS0066599
wikiData Q105165528