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[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aR,5R,6aR,6aR,6bR,8aR,10S,12aS,14aS,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-sulfooxy-1,3,4,5,6,6a,7,8,8a,10,11,12,14a,14b-tetradecahydropicene-4a-carboxylate

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 c0bfbdc7-7e69-4b44-bdab-91962b91246d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aR,5R,6aR,6aR,6bR,8aR,10S,12aS,14aS,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-sulfooxy-1,3,4,5,6,6a,7,8,8a,10,11,12,14a,14b-tetradecahydropicene-4a-carboxylate
SMILES (Canonical) CC1(CCC2(C(C1)C3C=CC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OS(=O)(=O)O)C)C(=O)OC6C(C(C(C(O6)COC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)O)O)O)C
SMILES (Isomeric) C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2C=C[C@@H]4[C@]3(C[C@H]([C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O)O)O)O)O)C)C)(C)C)OS(=O)(=O)O
InChI InChI=1S/C54H88O27S/c1-49(2)14-15-54(23(16-49)22-8-9-29-51(5)12-11-31(81-82(70,71)72)50(3,4)28(51)10-13-52(29,6)53(22,7)17-30(54)57)48(69)80-46-42(68)38(64)35(61)27(78-46)20-73-44-40(66)37(63)34(60)26(77-44)21-74-47-43(39(65)33(59)25(19-56)76-47)79-45-41(67)36(62)32(58)24(18-55)75-45/h8-9,22-47,55-68H,10-21H2,1-7H3,(H,70,71,72)/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+,51-,52+,53+,54+/m0/s1
InChI Key YLQRVVSAZUCERY-KGVNXVBHSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C54H88O27S
Molecular Weight 1201.30 g/mol
Exact Mass 1200.52336870 g/mol
Topological Polar Surface Area (TPSA) 446.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -3.38
H-Bond Acceptor 26
H-Bond Donor 15
Rotatable Bonds 14

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aR,5R,6aR,6aR,6bR,8aR,10S,12aS,14aS,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-sulfooxy-1,3,4,5,6,6a,7,8,8a,10,11,12,14a,14b-tetradecahydropicene-4a-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7163 71.63%
Caco-2 - 0.8690 86.90%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.8429 84.29%
Subcellular localzation Mitochondria 0.5430 54.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8106 81.06%
OATP1B3 inhibitior + 0.9071 90.71%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.9297 92.97%
P-glycoprotein inhibitior + 0.7446 74.46%
P-glycoprotein substrate + 0.5174 51.74%
CYP3A4 substrate + 0.7399 73.99%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8680 86.80%
CYP3A4 inhibition - 0.7914 79.14%
CYP2C9 inhibition - 0.7880 78.80%
CYP2C19 inhibition - 0.7410 74.10%
CYP2D6 inhibition - 0.8841 88.41%
CYP1A2 inhibition - 0.7612 76.12%
CYP2C8 inhibition + 0.6976 69.76%
CYP inhibitory promiscuity - 0.9606 96.06%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.6100 61.00%
Carcinogenicity (trinary) Non-required 0.6056 60.56%
Eye corrosion - 0.9735 97.35%
Eye irritation - 0.8983 89.83%
Skin irritation - 0.7677 76.77%
Skin corrosion - 0.9035 90.35%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7536 75.36%
Micronuclear + 0.5500 55.00%
Hepatotoxicity - 0.7701 77.01%
skin sensitisation - 0.8436 84.36%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity - 0.5625 56.25%
Nephrotoxicity - 0.9380 93.80%
Acute Oral Toxicity (c) III 0.6021 60.21%
Estrogen receptor binding + 0.7854 78.54%
Androgen receptor binding + 0.7529 75.29%
Thyroid receptor binding + 0.6411 64.11%
Glucocorticoid receptor binding + 0.7828 78.28%
Aromatase binding + 0.6238 62.38%
PPAR gamma + 0.8204 82.04%
Honey bee toxicity - 0.6118 61.18%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5355 53.55%
Fish aquatic toxicity + 0.9819 98.19%

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 98.21% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.92% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 94.11% 95.93%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.77% 94.45%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 93.77% 96.38%
CHEMBL5255 O00206 Toll-like receptor 4 93.00% 92.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.21% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.61% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 89.80% 96.61%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 89.28% 95.50%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 87.90% 94.33%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.82% 93.04%
CHEMBL1871 P10275 Androgen Receptor 86.52% 96.43%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.85% 95.56%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 85.71% 95.83%
CHEMBL4227 P25090 Lipoxin A4 receptor 85.05% 100.00%
CHEMBL2581 P07339 Cathepsin D 84.16% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.78% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.51% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 82.36% 97.25%
CHEMBL340 P08684 Cytochrome P450 3A4 81.33% 91.19%
CHEMBL2179 P04062 Beta-glucocerebrosidase 81.22% 85.31%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 80.72% 96.21%
CHEMBL5028 O14672 ADAM10 80.65% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.50% 95.89%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 80.36% 96.77%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.34% 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.
Bupleurum rotundifolium

Cross-Links

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PubChem 163106739
LOTUS LTS0101486
wikiData Q105350250