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dimethyl (1S,5R,6S,7S,8R,11S,12R,14R,15R)-7,14-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-3-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-12-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate

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 53622420-762e-4c76-ad20-fd48a1190310
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name dimethyl (1S,5R,6S,7S,8R,11S,12R,14R,15R)-7,14-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-3-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-12-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(C23COC(C2C(C(C4C3C1(CO4)C(=O)OC)O)(C)C56C7CC(C5(O6)C)C8C(O7)OC=C8O)C(=O)OC)O
SMILES (Isomeric) C/C=C(\C)/C(=O)O[C@@H]1C[C@H]([C@]23COC([C@H]2[C@]([C@@H]([C@H]4[C@H]3[C@@]1(CO4)C(=O)OC)O)(C)[C@@]56[C@@H]7C[C@H]([C@@]5(O6)C)[C@@H]8[C@H](O7)OC=C8O)C(=O)OC)O
InChI InChI=1S/C33H42O14/c1-7-13(2)25(37)45-17-9-16(35)31-11-44-21(26(38)40-5)22(31)29(3,24(36)20-23(31)32(17,12-43-20)28(39)41-6)33-18-8-14(30(33,4)47-33)19-15(34)10-42-27(19)46-18/h7,10,14,16-24,27,34-36H,8-9,11-12H2,1-6H3/b13-7+/t14-,16+,17+,18-,19-,20+,21?,22-,23+,24+,27-,29-,30-,31+,32-,33-/m0/s1
InChI Key DMQRBQYZSMVKIC-RPNFEMCRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C33H42O14
Molecular Weight 662.70 g/mol
Exact Mass 662.25745601 g/mol
Topological Polar Surface Area (TPSA) 189.00 Ų
XlogP 0.00
Atomic LogP (AlogP) 0.68
H-Bond Acceptor 14
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 dimethyl (1S,5R,6S,7S,8R,11S,12R,14R,15R)-7,14-dihydroxy-6-[(1S,2S,6S,8S,9R,11S)-3-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-12-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9567 95.67%
Caco-2 - 0.8381 83.81%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7312 73.12%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8061 80.61%
OATP1B3 inhibitior + 0.9596 95.96%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8868 88.68%
P-glycoprotein inhibitior + 0.7356 73.56%
P-glycoprotein substrate + 0.7584 75.84%
CYP3A4 substrate + 0.7305 73.05%
CYP2C9 substrate - 0.8071 80.71%
CYP2D6 substrate - 0.8829 88.29%
CYP3A4 inhibition - 0.7022 70.22%
CYP2C9 inhibition - 0.8504 85.04%
CYP2C19 inhibition - 0.8530 85.30%
CYP2D6 inhibition - 0.9395 93.95%
CYP1A2 inhibition - 0.8969 89.69%
CYP2C8 inhibition + 0.7424 74.24%
CYP inhibitory promiscuity - 0.9340 93.40%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5697 56.97%
Eye corrosion - 0.9859 98.59%
Eye irritation - 0.9165 91.65%
Skin irritation - 0.6869 68.69%
Skin corrosion - 0.9330 93.30%
Ames mutagenesis + 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4674 46.74%
Micronuclear - 0.5400 54.00%
Hepatotoxicity - 0.5375 53.75%
skin sensitisation - 0.8423 84.23%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.7271 72.71%
Acute Oral Toxicity (c) I 0.7042 70.42%
Estrogen receptor binding + 0.8005 80.05%
Androgen receptor binding + 0.7451 74.51%
Thyroid receptor binding + 0.5208 52.08%
Glucocorticoid receptor binding + 0.7210 72.10%
Aromatase binding + 0.6982 69.82%
PPAR gamma + 0.7264 72.64%
Honey bee toxicity - 0.7231 72.31%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9551 95.51%

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 99.01% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.39% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.25% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.10% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.45% 86.33%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 89.43% 91.07%
CHEMBL241 Q14432 Phosphodiesterase 3A 89.30% 92.94%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.59% 95.56%
CHEMBL284 P27487 Dipeptidyl peptidase IV 87.08% 95.69%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.01% 97.09%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.85% 99.23%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.80% 99.17%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.53% 100.00%
CHEMBL340 P08684 Cytochrome P450 3A4 84.00% 91.19%
CHEMBL221 P23219 Cyclooxygenase-1 83.79% 90.17%
CHEMBL3401 O75469 Pregnane X receptor 83.66% 94.73%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.18% 95.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.20% 94.00%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 81.44% 85.30%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.09% 96.00%

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
Azadirachta indica

Cross-Links

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PubChem 101919043
LOTUS LTS0182359
wikiData Q104392606