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Dimethyl (-)-(2aR,3R,4R,4aS,5R,7aS,8R,10S,10aR)-3,8,10-trihydroxy-4-[(2R,6R)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^2,6^0^9,11^]dodeca-3-en-9-yl]-4-methylperhydroisobenzofurano[5,4,3a-cd]isobenzofuran-5,10a-diacetate

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 4deeff18-8b5d-4d7b-9f5f-420e631bc627
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
IUPAC Name dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,15R)-7,12,14-trihydroxy-6-[(1S,2S,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate
SMILES (Canonical) CC12C3CC(C1(O2)C4(C5C(OCC56C(CC(C7(C6C(C4O)OC7)C(=O)OC)O)O)C(=O)OC)C)OC8C3(C=CO8)O.CC12C3CC(C1(O2)C4(C5C(OCC56C(CC(C7(C6C(C4O)OC7)C(=O)OC)O)O)C(=O)OC)C)OC8C3(C=CO8)O
SMILES (Isomeric) C[C@]12[C@H]3C[C@@H]([C@]1(O2)[C@]4([C@@H]5[C@H](OC[C@@]56[C@H](C[C@H]([C@@]7([C@@H]6[C@H]([C@H]4O)OC7)C(=O)OC)O)O)C(=O)OC)C)O[C@H]8[C@@]3(C=CO8)O.C[C@]12[C@H]3C[C@@H]([C@]1(O2)[C@]4([C@@H]5[C@H](OC[C@@]56[C@H](C[C@H]([C@@]7([C@@H]6[C@H]([C@H]4O)OC7)C(=O)OC)O)O)C(=O)OC)C)O[C@H]8[C@@]3(C=CO8)O
InChI InChI=1S/2C28H36O13/c2*1-23(28-14-7-11(24(28,2)41-28)27(34)5-6-37-22(27)40-14)17-16(20(32)35-3)39-9-25(17)12(29)8-13(30)26(21(33)36-4)10-38-15(18(25)26)19(23)31/h2*5-6,11-19,22,29-31,34H,7-10H2,1-4H3/t2*11-,12+,13-,14+,15-,16+,17+,18-,19-,22+,23+,24+,25-,26+,27+,28+/m11/s1
InChI Key XKWMYCSXXPNRMN-IYPYRUDMSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C56H72O26
Molecular Weight 1161.20 g/mol
Exact Mass 1160.43118240 g/mol
Topological Polar Surface Area (TPSA) 366.00 Ų
XlogP 0.00
Atomic LogP (AlogP) -3.22
H-Bond Acceptor 26
H-Bond Donor 8
Rotatable Bonds 6

Synonyms

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Dimethyl (-)-(2aR,3R,4R,4aS,5R,7aS,8R,10S,10aR)- 3,8,10-trihydroxy-4-[(2R,6R)-2-hydroxy-11-methyl- 5,7,10-trioxatetracyclo[6.3.1.0^2,6^0^9,11^]dodeca-3-en-9-yl]- 4-methylperhydroisobenzofurano[5,4,3a-cd]isobenzofuran-5,10a-diacetate

2D Structure

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2D Structure of Dimethyl (-)-(2aR,3R,4R,4aS,5R,7aS,8R,10S,10aR)-3,8,10-trihydroxy-4-[(2R,6R)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^2,6^0^9,11^]dodeca-3-en-9-yl]-4-methylperhydroisobenzofurano[5,4,3a-cd]isobenzofuran-5,10a-diacetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8681 86.81%
Caco-2 - 0.8537 85.37%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.6384 63.84%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8390 83.90%
OATP1B3 inhibitior + 0.9472 94.72%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.8591 85.91%
P-glycoprotein inhibitior + 0.7236 72.36%
P-glycoprotein substrate + 0.6558 65.58%
CYP3A4 substrate + 0.7227 72.27%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8621 86.21%
CYP3A4 inhibition - 0.7493 74.93%
CYP2C9 inhibition - 0.8733 87.33%
CYP2C19 inhibition - 0.8747 87.47%
CYP2D6 inhibition - 0.9378 93.78%
CYP1A2 inhibition - 0.9267 92.67%
CYP2C8 inhibition + 0.6908 69.08%
CYP inhibitory promiscuity - 0.9453 94.53%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6101 61.01%
Eye corrosion - 0.9847 98.47%
Eye irritation - 0.9018 90.18%
Skin irritation - 0.7333 73.33%
Skin corrosion - 0.9281 92.81%
Ames mutagenesis + 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4541 45.41%
Micronuclear - 0.5500 55.00%
Hepatotoxicity - 0.6625 66.25%
skin sensitisation - 0.8556 85.56%
Respiratory toxicity + 0.7222 72.22%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.5503 55.03%
Acute Oral Toxicity (c) I 0.6438 64.38%
Estrogen receptor binding + 0.7558 75.58%
Androgen receptor binding + 0.7748 77.48%
Thyroid receptor binding + 0.5562 55.62%
Glucocorticoid receptor binding + 0.6863 68.63%
Aromatase binding + 0.6449 64.49%
PPAR gamma + 0.7450 74.50%
Honey bee toxicity - 0.8591 85.91%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9232 92.32%

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 98.23% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.96% 96.09%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 90.26% 91.07%
CHEMBL221 P23219 Cyclooxygenase-1 89.63% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.44% 94.45%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.78% 85.14%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.10% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.11% 97.09%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 83.88% 85.30%
CHEMBL2094127 P06493 Cyclin-dependent kinase 1/cyclin B 83.53% 96.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.13% 92.62%
CHEMBL340 P08684 Cytochrome P450 3A4 82.81% 91.19%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.29% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 81.99% 99.23%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.61% 100.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.87% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.64% 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.
Azadirachta indica

Cross-Links

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PubChem 139058734
LOTUS LTS0112448
wikiData Q104398898