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(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2S,3R,5S)-2-butoxy-3-hydroxy-5-(2-methylprop-1-enyl)oxolan-3-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

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 b8ad4aaa-d135-42dd-9486-e8c75b5282f1
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2S,3R,5S)-2-butoxy-3-hydroxy-5-(2-methylprop-1-enyl)oxolan-3-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
SMILES (Canonical) CCCCOC1C(CC(O1)C=C(C)C)(C2CCC3(C2CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)C)O
SMILES (Isomeric) CCCCO[C@@H]1[C@@](C[C@H](O1)C=C(C)C)([C@H]2CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)C)O
InChI InChI=1S/C51H86O17/c1-10-11-20-61-46-51(60,22-27(64-46)21-25(2)3)29-14-18-49(8)28(29)12-13-33-48(7)17-16-34(47(5,6)32(48)15-19-50(33,49)9)66-45-42(68-44-40(59)38(57)35(54)26(4)63-44)41(37(56)31(23-52)65-45)67-43-39(58)36(55)30(53)24-62-43/h21,26-46,52-60H,10-20,22-24H2,1-9H3/t26-,27+,28+,29-,30+,31+,32-,33+,34-,35-,36-,37+,38+,39+,40+,41-,42+,43-,44-,45-,46-,48-,49+,50+,51+/m0/s1
InChI Key XCYYAAAJROIVTP-JDEUSJJSSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C51H86O17
Molecular Weight 971.20 g/mol
Exact Mass 970.58650127 g/mol
Topological Polar Surface Area (TPSA) 256.00 Ų
XlogP 4.40
Atomic LogP (AlogP) 2.80
H-Bond Acceptor 17
H-Bond Donor 9
Rotatable Bonds 13

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(2S,3R,5S)-2-butoxy-3-hydroxy-5-(2-methylprop-1-enyl)oxolan-3-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8762 87.62%
Caco-2 - 0.8904 89.04%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7367 73.67%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8202 82.02%
OATP1B3 inhibitior + 0.9171 91.71%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.8568 85.68%
P-glycoprotein inhibitior + 0.7586 75.86%
P-glycoprotein substrate + 0.6436 64.36%
CYP3A4 substrate + 0.7551 75.51%
CYP2C9 substrate - 0.7890 78.90%
CYP2D6 substrate - 0.8406 84.06%
CYP3A4 inhibition - 0.7868 78.68%
CYP2C9 inhibition - 0.8293 82.93%
CYP2C19 inhibition - 0.8732 87.32%
CYP2D6 inhibition - 0.9197 91.97%
CYP1A2 inhibition - 0.8993 89.93%
CYP2C8 inhibition + 0.7904 79.04%
CYP inhibitory promiscuity - 0.8228 82.28%
UGT catelyzed - 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5695 56.95%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9052 90.52%
Skin irritation - 0.5958 59.58%
Skin corrosion - 0.9421 94.21%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7933 79.33%
Micronuclear - 0.8300 83.00%
Hepatotoxicity - 0.8375 83.75%
skin sensitisation - 0.9020 90.20%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity - 0.5250 52.50%
Nephrotoxicity - 0.9378 93.78%
Acute Oral Toxicity (c) I 0.6136 61.36%
Estrogen receptor binding + 0.7935 79.35%
Androgen receptor binding + 0.7430 74.30%
Thyroid receptor binding - 0.5480 54.80%
Glucocorticoid receptor binding + 0.7016 70.16%
Aromatase binding + 0.6641 66.41%
PPAR gamma + 0.7821 78.21%
Honey bee toxicity - 0.6159 61.59%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity + 0.6191 61.91%
Fish aquatic toxicity + 0.9620 96.20%

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 97.55% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.30% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.70% 97.25%
CHEMBL226 P30542 Adenosine A1 receptor 95.13% 95.93%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.92% 96.61%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 94.66% 91.24%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 92.74% 92.86%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.73% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.71% 97.09%
CHEMBL2243 O00519 Anandamide amidohydrolase 92.18% 97.53%
CHEMBL241 Q14432 Phosphodiesterase 3A 92.10% 92.94%
CHEMBL2581 P07339 Cathepsin D 91.07% 98.95%
CHEMBL279 P35968 Vascular endothelial growth factor receptor 2 90.91% 95.52%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 90.76% 92.88%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 90.22% 95.50%
CHEMBL3892 Q99500 Sphingosine 1-phosphate receptor Edg-3 90.05% 97.29%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 89.85% 97.86%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.62% 100.00%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 89.45% 100.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.50% 99.17%
CHEMBL1974 P36888 Tyrosine-protein kinase receptor FLT3 87.96% 91.83%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.43% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.36% 89.00%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 87.15% 96.77%
CHEMBL202 P00374 Dihydrofolate reductase 86.86% 89.92%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.53% 95.89%
CHEMBL3589 P55263 Adenosine kinase 86.10% 98.05%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 85.69% 91.03%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 85.64% 92.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.63% 95.89%
CHEMBL2534 O15530 3-phosphoinositide dependent protein kinase-1 84.42% 95.36%
CHEMBL5255 O00206 Toll-like receptor 4 83.90% 92.50%
CHEMBL3714130 P46095 G-protein coupled receptor 6 83.62% 97.36%
CHEMBL4302 P08183 P-glycoprotein 1 83.32% 92.98%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 83.20% 100.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.87% 96.21%
CHEMBL1075162 Q13304 Uracil nucleotide/cysteinyl leukotriene receptor 82.52% 80.33%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.41% 100.00%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 82.15% 89.05%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 80.45% 93.00%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 80.35% 95.83%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 80.24% 92.32%
CHEMBL242 Q92731 Estrogen receptor beta 80.12% 98.35%

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.
Gynostemma pentaphyllum

Cross-Links

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PubChem 162944070
LOTUS LTS0087558
wikiData Q105325564