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(1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-9-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-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 2575b874-859e-458f-acaf-803c36212b4d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-9-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC4CCC5(C6CCC7C8C(CCC8(CCC7(C6(CCC5C4(C)C(=O)O)C)C)C(=O)OC9C(C(C(C(O9)CO)O)O)O)C(=C)C)C)O)O)O)CO)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)O[C@H]4CC[C@@]5([C@H]6CC[C@@H]7[C@H]8[C@@H](CC[C@@]8(CC[C@]7([C@@]6(CC[C@H]5[C@]4(C)C(=O)O)C)C)C(=O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)C(=C)C)C)O)O)O)CO)O)O)O
InChI InChI=1S/C54H86O24/c1-21(2)23-10-15-54(49(70)78-47-41(66)36(61)33(58)25(18-55)73-47)17-16-51(5)24(31(23)54)8-9-28-50(4)13-12-30(53(7,48(68)69)29(50)11-14-52(28,51)6)76-46-40(65)37(62)34(59)27(75-46)20-71-44-42(67)38(63)43(26(19-56)74-44)77-45-39(64)35(60)32(57)22(3)72-45/h22-47,55-67H,1,8-20H2,2-7H3,(H,68,69)/t22-,23-,24+,25+,26+,27+,28+,29+,30-,31+,32-,33+,34+,35+,36-,37-,38+,39+,40+,41+,42+,43+,44+,45-,46-,47-,50+,51+,52+,53-,54-/m0/s1
InChI Key KNUPOIPCOLQCRE-YZWKWLGBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C54H86O24
Molecular Weight 1119.20 g/mol
Exact Mass 1118.55090361 g/mol
Topological Polar Surface Area (TPSA) 391.00 Ų
XlogP -0.30
Atomic LogP (AlogP) -2.09
H-Bond Acceptor 23
H-Bond Donor 14
Rotatable Bonds 13

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (1R,3aS,5aR,5bR,7aR,8S,9S,11aR,11bR,13aR,13bR)-9-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-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 + 0.6096 60.96%
Caco-2 - 0.8783 87.83%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.8115 81.15%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8520 85.20%
OATP1B3 inhibitior + 0.8498 84.98%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6048 60.48%
BSEP inhibitior + 0.8924 89.24%
P-glycoprotein inhibitior + 0.7451 74.51%
P-glycoprotein substrate + 0.5500 55.00%
CYP3A4 substrate + 0.7334 73.34%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8776 87.76%
CYP3A4 inhibition - 0.9079 90.79%
CYP2C9 inhibition - 0.9014 90.14%
CYP2C19 inhibition - 0.9100 91.00%
CYP2D6 inhibition - 0.9530 95.30%
CYP1A2 inhibition - 0.8903 89.03%
CYP2C8 inhibition + 0.7620 76.20%
CYP inhibitory promiscuity - 0.9446 94.46%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6732 67.32%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.9005 90.05%
Skin irritation - 0.5122 51.22%
Skin corrosion - 0.9403 94.03%
Ames mutagenesis - 0.6670 66.70%
Human Ether-a-go-go-Related Gene inhibition + 0.7691 76.91%
Micronuclear - 0.8400 84.00%
Hepatotoxicity - 0.7973 79.73%
skin sensitisation - 0.9225 92.25%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.5625 56.25%
Nephrotoxicity - 0.9047 90.47%
Acute Oral Toxicity (c) III 0.4375 43.75%
Estrogen receptor binding + 0.8091 80.91%
Androgen receptor binding + 0.7574 75.74%
Thyroid receptor binding + 0.5708 57.08%
Glucocorticoid receptor binding + 0.7533 75.33%
Aromatase binding + 0.6567 65.67%
PPAR gamma + 0.8171 81.71%
Honey bee toxicity - 0.5953 59.53%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6600 66.00%
Fish aquatic toxicity + 0.9810 98.10%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.88% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.07% 91.11%
CHEMBL233 P35372 Mu opioid receptor 95.95% 97.93%
CHEMBL218 P21554 Cannabinoid CB1 receptor 94.21% 96.61%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.51% 86.33%
CHEMBL3714130 P46095 G-protein coupled receptor 6 91.64% 97.36%
CHEMBL5888 Q99558 Mitogen-activated protein kinase kinase kinase 14 88.79% 100.00%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 88.44% 96.09%
CHEMBL2581 P07339 Cathepsin D 88.40% 98.95%
CHEMBL340 P08684 Cytochrome P450 3A4 88.28% 91.19%
CHEMBL241 Q14432 Phosphodiesterase 3A 88.10% 92.94%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 87.46% 96.38%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.25% 89.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.05% 95.50%
CHEMBL5255 O00206 Toll-like receptor 4 86.58% 92.50%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 86.25% 95.89%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 85.86% 93.04%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.60% 95.83%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.56% 97.25%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.17% 97.09%
CHEMBL4618 P09960 Leukotriene A4 hydrolase 83.98% 97.86%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.87% 94.45%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 83.44% 97.33%
CHEMBL226 P30542 Adenosine A1 receptor 83.28% 95.93%
CHEMBL237 P41145 Kappa opioid receptor 83.21% 98.10%
CHEMBL5028 O14672 ADAM10 82.77% 97.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 82.36% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.11% 100.00%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 82.04% 91.24%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.74% 95.89%
CHEMBL2072 P35499 Sodium channel protein type IV alpha subunit 81.60% 92.32%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 81.60% 100.00%
CHEMBL1293316 Q9HBX9 Relaxin receptor 1 81.59% 82.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.43% 99.17%
CHEMBL2243 O00519 Anandamide amidohydrolase 81.23% 97.53%
CHEMBL2955 O95136 Sphingosine 1-phosphate receptor Edg-5 80.98% 92.86%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.10% 92.62%

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.
Bupleurum fruticescens

Cross-Links

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PubChem 102119831
LOTUS LTS0116767
wikiData Q105143579