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methyl (1S,2R,4S,6S,7R,8R,9R,10R,11S,12S,14R,15S,16R,18R)-8,12,18-triacetyloxy-6-(furan-3-yl)-9,14-dihydroxy-1,7,11,15-tetramethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecane-15-carboxylate

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 1e03cb11-864c-4250-a7df-dbed986014d6
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name methyl (1S,2R,4S,6S,7R,8R,9R,10R,11S,12S,14R,15S,16R,18R)-8,12,18-triacetyloxy-6-(furan-3-yl)-9,14-dihydroxy-1,7,11,15-tetramethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecane-15-carboxylate
SMILES (Canonical) CC(=O)OC1CC2C(C(CC(C2(C3C1(C45C(O4)CC(C5(C(C3O)OC(=O)C)C)C6=COC=C6)C)C)OC(=O)C)O)(C)C(=O)OC
SMILES (Isomeric) CC(=O)O[C@@H]1C[C@H]2[C@]([C@@H](C[C@@H]([C@@]2([C@@H]3[C@@]1([C@@]45[C@@H](O4)C[C@H]([C@@]5([C@H]([C@@H]3O)OC(=O)C)C)C6=COC=C6)C)C)OC(=O)C)O)(C)C(=O)OC
InChI InChI=1S/C33H44O12/c1-15(34)42-22-13-21(37)29(4,28(39)40-8)20-12-23(43-16(2)35)32(7)26(30(20,22)5)25(38)27(44-17(3)36)31(6)19(18-9-10-41-14-18)11-24-33(31,32)45-24/h9-10,14,19-27,37-38H,11-13H2,1-8H3/t19-,20-,21+,22-,23+,24-,25+,26+,27-,29-,30+,31+,32+,33-/m0/s1
InChI Key TWPWWURUWNUYQE-FLGYXFMESA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C33H44O12
Molecular Weight 632.70 g/mol
Exact Mass 632.28327683 g/mol
Topological Polar Surface Area (TPSA) 171.00 Ų
XlogP 2.70
Atomic LogP (AlogP) 2.67
H-Bond Acceptor 12
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (1S,2R,4S,6S,7R,8R,9R,10R,11S,12S,14R,15S,16R,18R)-8,12,18-triacetyloxy-6-(furan-3-yl)-9,14-dihydroxy-1,7,11,15-tetramethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecane-15-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9413 94.13%
Caco-2 - 0.8013 80.13%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.5143 51.43%
Subcellular localzation Mitochondria 0.6699 66.99%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7245 72.45%
OATP1B3 inhibitior + 0.8123 81.23%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9437 94.37%
P-glycoprotein inhibitior + 0.7394 73.94%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.6912 69.12%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8089 80.89%
CYP3A4 inhibition + 0.5987 59.87%
CYP2C9 inhibition - 0.8777 87.77%
CYP2C19 inhibition - 0.8912 89.12%
CYP2D6 inhibition - 0.9095 90.95%
CYP1A2 inhibition - 0.8949 89.49%
CYP2C8 inhibition + 0.6825 68.25%
CYP inhibitory promiscuity - 0.9084 90.84%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.4370 43.70%
Eye corrosion - 0.9890 98.90%
Eye irritation - 0.8929 89.29%
Skin irritation - 0.7244 72.44%
Skin corrosion - 0.9153 91.53%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7697 76.97%
Micronuclear + 0.5400 54.00%
Hepatotoxicity + 0.6250 62.50%
skin sensitisation - 0.8658 86.58%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity + 0.5602 56.02%
Acute Oral Toxicity (c) I 0.5107 51.07%
Estrogen receptor binding + 0.7850 78.50%
Androgen receptor binding + 0.7184 71.84%
Thyroid receptor binding + 0.6010 60.10%
Glucocorticoid receptor binding + 0.7524 75.24%
Aromatase binding + 0.7404 74.04%
PPAR gamma + 0.7356 73.56%
Honey bee toxicity - 0.7355 73.55%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.8771 87.71%

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 98.87% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.28% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.21% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.37% 94.45%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 91.72% 81.11%
CHEMBL340 P08684 Cytochrome P450 3A4 90.20% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.95% 97.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.88% 94.00%
CHEMBL4040 P28482 MAP kinase ERK2 85.54% 83.82%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.23% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.56% 95.56%
CHEMBL5028 O14672 ADAM10 83.46% 97.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.16% 89.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 82.59% 91.24%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.42% 100.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 82.38% 96.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 81.71% 96.77%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.36% 97.14%
CHEMBL3401 O75469 Pregnane X receptor 80.82% 94.73%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.36% 93.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.28% 86.33%

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.
Turraea heterophylla

Cross-Links

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PubChem 162944787
LOTUS LTS0095507
wikiData Q105265999