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(2S,3R,4S,4aR,6aR,6bR,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4-hydroxy-6-methyloxan-2-yl]oxycarbonyl-2-hydroxy-6b-(hydroxymethyl)-4,6a,11,11,14b-pentamethyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid

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 bad55b11-c3cc-49f1-b305-36592a8b75bd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3R,4S,4aR,6aR,6bR,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4-hydroxy-6-methyloxan-2-yl]oxycarbonyl-2-hydroxy-6b-(hydroxymethyl)-4,6a,11,11,14b-pentamethyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(C(OC2OC(=O)C34CCC(CC3C5=CCC6C(C5(CC4)CO)(CCC7C6(CC(C(C7(C)C(=O)O)OC8C(C(C(C(O8)CO)O)O)O)O)C)C)(C)C)C)OC(=O)C=CC9=CC(=C(C=C9)OC)OC)O)O)O)OC1C(C(C(CO1)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2OC(=O)[C@@]34CC[C@@]5(C(=CC[C@H]6[C@]5(CC[C@@H]7[C@@]6(C[C@@H]([C@@H]([C@@]7(C)C(=O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O)O)C)C)[C@@H]3CC(CC4)(C)C)CO)C)OC(=O)/C=C/C9=CC(=C(C=C9)OC)OC)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O
InChI InChI=1S/C64H94O27/c1-28-49(88-53-45(74)41(70)34(68)26-83-53)44(73)47(76)54(84-28)89-51-48(77)50(87-40(69)15-11-30-10-13-35(81-8)36(22-30)82-9)29(2)85-56(51)91-58(80)63-19-18-59(3,4)23-32(63)31-12-14-38-60(5)24-33(67)52(90-55-46(75)43(72)42(71)37(25-65)86-55)62(7,57(78)79)39(60)16-17-61(38,6)64(31,27-66)21-20-63/h10-13,15,22,28-29,32-34,37-39,41-56,65-68,70-77H,14,16-21,23-27H2,1-9H3,(H,78,79)/b15-11+/t28-,29+,32-,33-,34+,37+,38+,39+,41-,42-,43-,44-,45+,46+,47+,48-,49-,50-,51+,52-,53-,54-,55-,56-,60+,61+,62-,63-,64-/m0/s1
InChI Key BFZSPLROFPCIFL-YTRPWXPDSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C64H94O27
Molecular Weight 1295.40 g/mol
Exact Mass 1294.59824772 g/mol
Topological Polar Surface Area (TPSA) 416.00 Ų
XlogP 0.90
Atomic LogP (AlogP) -0.05
H-Bond Acceptor 26
H-Bond Donor 13
Rotatable Bonds 16

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,4aR,6aR,6bR,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-5-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]oxy-4-hydroxy-6-methyloxan-2-yl]oxycarbonyl-2-hydroxy-6b-(hydroxymethyl)-4,6a,11,11,14b-pentamethyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8680 86.80%
Caco-2 - 0.8608 86.08%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.7598 75.98%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8009 80.09%
OATP1B3 inhibitior - 0.2595 25.95%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.9683 96.83%
P-glycoprotein inhibitior + 0.7431 74.31%
P-glycoprotein substrate + 0.7228 72.28%
CYP3A4 substrate + 0.7442 74.42%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8706 87.06%
CYP3A4 inhibition - 0.7405 74.05%
CYP2C9 inhibition - 0.8191 81.91%
CYP2C19 inhibition - 0.8017 80.17%
CYP2D6 inhibition - 0.9173 91.73%
CYP1A2 inhibition - 0.7097 70.97%
CYP2C8 inhibition + 0.8402 84.02%
CYP inhibitory promiscuity - 0.9547 95.47%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9400 94.00%
Carcinogenicity (trinary) Non-required 0.6274 62.74%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.8966 89.66%
Skin irritation - 0.7231 72.31%
Skin corrosion - 0.9432 94.32%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7529 75.29%
Micronuclear - 0.7400 74.00%
Hepatotoxicity - 0.7591 75.91%
skin sensitisation - 0.8834 88.34%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.9255 92.55%
Acute Oral Toxicity (c) III 0.5612 56.12%
Estrogen receptor binding + 0.6309 63.09%
Androgen receptor binding + 0.7618 76.18%
Thyroid receptor binding + 0.7307 73.07%
Glucocorticoid receptor binding + 0.8109 81.09%
Aromatase binding + 0.7130 71.30%
PPAR gamma + 0.8316 83.16%
Honey bee toxicity - 0.6413 64.13%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9815 98.15%

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 99.69% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 98.95% 86.33%
CHEMBL4302 P08183 P-glycoprotein 1 97.76% 92.98%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.69% 96.09%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 96.06% 96.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 95.32% 97.36%
CHEMBL241 Q14432 Phosphodiesterase 3A 94.24% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.98% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.15% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.07% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 90.55% 91.07%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.69% 94.45%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 89.65% 89.62%
CHEMBL221 P23219 Cyclooxygenase-1 87.75% 90.17%
CHEMBL5028 O14672 ADAM10 86.93% 97.50%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 86.22% 95.17%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 84.47% 96.21%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.15% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.07% 100.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.57% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.57% 97.14%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 82.84% 93.00%
CHEMBL2581 P07339 Cathepsin D 82.70% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.56% 92.62%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.16% 86.92%
CHEMBL4829 O00763 Acetyl-CoA carboxylase 2 81.55% 98.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.19% 99.17%
CHEMBL340 P08684 Cytochrome P450 3A4 80.14% 91.19%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 162909159
LOTUS LTS0153481
wikiData Q104935116