[(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-2-[[(1S,2S,4S,5R,8R,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] acetate

Details

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Internal ID 0aa6ef9f-2243-4bae-a1e5-9ba2608caedf
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)-3,5-dihydroxy-2-[[(1S,2S,4S,5R,8R,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] acetate
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC56C4(CC(C7(C5CC(CC7)(C)C)CO6)O)C)C)C)O)OC8C(C(C(C(O8)CO)OC(=O)C)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=C[C@@]56[C@]4(C[C@@H]([C@@]7([C@H]5CC(CC7)(C)C)CO6)O)C)C)C)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)OC(=O)C)O)O)O
InChI InChI=1S/C44H70O14/c1-22-30(49)35(58-36-32(51)31(50)34(55-23(2)47)24(19-45)56-36)33(52)37(54-22)57-29-11-12-39(5)25(40(29,6)20-46)9-13-41(7)26(39)10-14-44-27-17-38(3,4)15-16-43(27,21-53-44)28(48)18-42(41,44)8/h10,14,22,24-37,45-46,48-52H,9,11-13,15-21H2,1-8H3/t22-,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,34-,35+,36+,37+,39+,40+,41-,42+,43-,44+/m1/s1
InChI Key PAEBOQPQAZCVKP-TVYJJVMUSA-N
Popularity 3 references in papers

Physical and Chemical Properties

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Molecular Formula C44H70O14
Molecular Weight 823.00 g/mol
Exact Mass 822.47655690 g/mol
Topological Polar Surface Area (TPSA) 214.00 Ų
XlogP 2.50
Atomic LogP (AlogP) 2.35
H-Bond Acceptor 14
H-Bond Donor 7
Rotatable Bonds 7

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)-3,5-dihydroxy-2-[[(1S,2S,4S,5R,8R,9R,10S,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.01,18.04,17.05,14.08,13]tetracos-15-en-10-yl]oxy]-6-methyloxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7235 72.35%
Caco-2 - 0.8779 87.79%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.7561 75.61%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8308 83.08%
OATP1B3 inhibitior + 0.9009 90.09%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior + 0.6525 65.25%
P-glycoprotein inhibitior + 0.7595 75.95%
P-glycoprotein substrate + 0.5600 56.00%
CYP3A4 substrate + 0.7369 73.69%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8785 87.85%
CYP3A4 inhibition - 0.9130 91.30%
CYP2C9 inhibition - 0.8588 85.88%
CYP2C19 inhibition - 0.8720 87.20%
CYP2D6 inhibition - 0.9479 94.79%
CYP1A2 inhibition - 0.9165 91.65%
CYP2C8 inhibition + 0.6896 68.96%
CYP inhibitory promiscuity - 0.9568 95.68%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6305 63.05%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.9058 90.58%
Skin irritation - 0.6279 62.79%
Skin corrosion - 0.9429 94.29%
Ames mutagenesis - 0.6670 66.70%
Human Ether-a-go-go-Related Gene inhibition + 0.6605 66.05%
Micronuclear - 0.8900 89.00%
Hepatotoxicity - 0.5887 58.87%
skin sensitisation - 0.9113 91.13%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.7222 72.22%
Mitochondrial toxicity - 0.6000 60.00%
Nephrotoxicity - 0.6248 62.48%
Acute Oral Toxicity (c) I 0.6357 63.57%
Estrogen receptor binding + 0.7509 75.09%
Androgen receptor binding + 0.7532 75.32%
Thyroid receptor binding - 0.5509 55.09%
Glucocorticoid receptor binding + 0.6984 69.84%
Aromatase binding + 0.6514 65.14%
PPAR gamma + 0.7588 75.88%
Honey bee toxicity - 0.6605 66.05%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9406 94.06%

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 96.87% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.67% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.96% 94.45%
CHEMBL3714130 P46095 G-protein coupled receptor 6 93.80% 97.36%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.01% 86.33%
CHEMBL226 P30542 Adenosine A1 receptor 90.22% 95.93%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.96% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.61% 95.89%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 88.21% 95.50%
CHEMBL4005 P42336 PI3-kinase p110-alpha subunit 87.69% 97.47%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.49% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.15% 97.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 86.56% 96.38%
CHEMBL2581 P07339 Cathepsin D 86.02% 98.95%
CHEMBL1907601 P11802 Cyclin-dependent kinase 4/cyclin D1 83.46% 98.99%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.29% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.05% 94.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.70% 95.89%
CHEMBL2842 P42345 Serine/threonine-protein kinase mTOR 82.66% 92.78%
CHEMBL1293277 O15118 Niemann-Pick C1 protein 82.49% 81.11%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.39% 86.92%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.36% 92.62%
CHEMBL2096618 P11274 Bcr/Abl fusion protein 82.32% 85.83%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.10% 94.00%
CHEMBL5028 O14672 ADAM10 82.06% 97.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.69% 91.07%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 81.10% 91.24%
CHEMBL5255 O00206 Toll-like receptor 4 80.54% 92.50%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 80.34% 93.04%
CHEMBL2274 Q9H228 Sphingosine 1-phosphate receptor Edg-8 80.30% 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 chinense
Bupleurum falcatum
Bupleurum kunmingense
Bupleurum polyclonum
Bupleurum scorzonerifolium

Cross-Links

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PubChem 101690814
NPASS NPC101218
LOTUS LTS0159118
wikiData Q105204471