[(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(3S,4R,4aR,6aR,6bS,8R,8aS,11R,14aR,14bS)-8-hydroxy-4,8a,11-tris(hydroxymethyl)-4,6a,6b,11,14b-pentamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] hydrogen sulfate

Details

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Internal ID f0e4fd80-db8c-4980-aaa6-2af891b0f2c7
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name [(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(3S,4R,4aR,6aR,6bS,8R,8aS,11R,14aR,14bS)-8-hydroxy-4,8a,11-tris(hydroxymethyl)-4,6a,6b,11,14b-pentamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] hydrogen sulfate
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC5=C6CC(CCC6(C(CC54C)O)CO)(C)CO)C)C)OC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(C(O8)CO)OS(=O)(=O)O)O)O)O
SMILES (Isomeric) C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]4([C@@H]3C=CC5=C6C[C@](CC[C@@]6([C@@H](C[C@]54C)O)CO)(C)CO)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)OS(=O)(=O)O)O)O)O
InChI InChI=1S/C48H78O22S/c1-22-31(55)38(68-41-36(60)34(58)37(26(18-50)66-41)70-71(61,62)63)39(69-40-35(59)33(57)32(56)25(17-49)65-40)42(64-22)67-30-10-11-44(3)27(45(30,4)20-52)9-12-46(5)28(44)8-7-23-24-15-43(2,19-51)13-14-48(24,21-53)29(54)16-47(23,46)6/h7-8,22,25-42,49-60H,9-21H2,1-6H3,(H,61,62,63)/t22-,25-,26-,27-,28-,29-,30+,31+,32-,33+,34-,35-,36-,37-,38+,39-,40+,41+,42+,43-,44+,45+,46-,47-,48-/m1/s1
InChI Key ZZEVXJGMALBHKL-FZKUTRKTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C48H78O22S
Molecular Weight 1039.20 g/mol
Exact Mass 1038.47054529 g/mol
Topological Polar Surface Area (TPSA) 370.00 Ų
XlogP -1.40
Atomic LogP (AlogP) -1.70
H-Bond Acceptor 21
H-Bond Donor 13
Rotatable Bonds 13

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(3S,4R,4aR,6aR,6bS,8R,8aS,11R,14aR,14bS)-8-hydroxy-4,8a,11-tris(hydroxymethyl)-4,6a,6b,11,14b-pentamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] hydrogen sulfate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7425 74.25%
Caco-2 - 0.8791 87.91%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.4841 48.41%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8265 82.65%
OATP1B3 inhibitior + 0.9188 91.88%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.6521 65.21%
BSEP inhibitior + 0.6803 68.03%
P-glycoprotein inhibitior + 0.7486 74.86%
P-glycoprotein substrate + 0.6169 61.69%
CYP3A4 substrate + 0.7447 74.47%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8586 85.86%
CYP3A4 inhibition - 0.8429 84.29%
CYP2C9 inhibition - 0.7684 76.84%
CYP2C19 inhibition - 0.7231 72.31%
CYP2D6 inhibition - 0.8708 87.08%
CYP1A2 inhibition - 0.7445 74.45%
CYP2C8 inhibition + 0.7360 73.60%
CYP inhibitory promiscuity - 0.9296 92.96%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.6100 61.00%
Carcinogenicity (trinary) Non-required 0.5731 57.31%
Eye corrosion - 0.9788 97.88%
Eye irritation - 0.9023 90.23%
Skin irritation - 0.7473 74.73%
Skin corrosion - 0.9067 90.67%
Ames mutagenesis - 0.8000 80.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6522 65.22%
Micronuclear + 0.5900 59.00%
Hepatotoxicity + 0.7250 72.50%
skin sensitisation - 0.8351 83.51%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity - 0.5375 53.75%
Nephrotoxicity - 0.7644 76.44%
Acute Oral Toxicity (c) III 0.5913 59.13%
Estrogen receptor binding + 0.7926 79.26%
Androgen receptor binding + 0.7458 74.58%
Thyroid receptor binding - 0.5319 53.19%
Glucocorticoid receptor binding + 0.6924 69.24%
Aromatase binding + 0.6163 61.63%
PPAR gamma + 0.7881 78.81%
Honey bee toxicity - 0.6341 63.41%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9772 97.72%

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 96.18% 91.11%
CHEMBL1994 P08235 Mineralocorticoid receptor 93.30% 100.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.96% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.09% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 90.40% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 89.65% 97.36%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.29% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.90% 89.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 87.70% 95.50%
CHEMBL226 P30542 Adenosine A1 receptor 87.46% 95.93%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.31% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.99% 95.89%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 86.49% 97.33%
CHEMBL1937 Q92769 Histone deacetylase 2 86.29% 94.75%
CHEMBL3476 O15111 Inhibitor of nuclear factor kappa B kinase alpha subunit 86.15% 95.83%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 85.07% 91.24%
CHEMBL2581 P07339 Cathepsin D 84.90% 98.95%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.89% 96.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.17% 95.89%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.98% 96.90%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 80.40% 94.33%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.24% 100.00%

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 rigidum

Cross-Links

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PubChem 101084508
LOTUS LTS0078634
wikiData Q105386751