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(2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8R,8aS,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-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 803b7cc4-af55-459d-aaac-6652a238bcfc
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8R,8aS,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C(C2(C)C)CCC4(C3C=CC5=C6CC(CCC6(C(CC54C)O)CO)(C)C)C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(CO8)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](C2(C)C)CC[C@@]4([C@@H]3C=CC5=C6CC(CC[C@@]6([C@@H](C[C@]54C)O)CO)(C)C)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O
InChI InChI=1S/C47H76O16/c1-22-31(52)34(55)37(63-41-38(35(56)33(54)26(19-48)60-41)62-39-36(57)32(53)25(50)20-58-39)40(59-22)61-30-12-13-44(6)27(43(30,4)5)11-14-45(7)28(44)10-9-23-24-17-42(2,3)15-16-47(24,21-49)29(51)18-46(23,45)8/h9-10,22,25-41,48-57H,11-21H2,1-8H3/t22-,25-,26-,27+,28-,29-,30+,31+,32+,33-,34+,35+,36-,37-,38-,39+,40+,41+,44+,45-,46-,47-/m1/s1
InChI Key GWDRPRWADKYHLP-ZCUSHYMQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C47H76O16
Molecular Weight 897.10 g/mol
Exact Mass 896.51333633 g/mol
Topological Polar Surface Area (TPSA) 258.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.17
H-Bond Acceptor 16
H-Bond Donor 10
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8R,8aS,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-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 + 0.7084 70.84%
Caco-2 - 0.8921 89.21%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8571 85.71%
Subcellular localzation Mitochondria 0.7876 78.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7638 76.38%
OATP1B3 inhibitior - 0.4367 43.67%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.7726 77.26%
P-glycoprotein inhibitior + 0.7495 74.95%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7393 73.93%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8401 84.01%
CYP3A4 inhibition - 0.9345 93.45%
CYP2C9 inhibition - 0.8819 88.19%
CYP2C19 inhibition - 0.8988 89.88%
CYP2D6 inhibition - 0.9401 94.01%
CYP1A2 inhibition - 0.8923 89.23%
CYP2C8 inhibition + 0.6864 68.64%
CYP inhibitory promiscuity - 0.9600 96.00%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6252 62.52%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9076 90.76%
Skin irritation - 0.6425 64.25%
Skin corrosion - 0.9480 94.80%
Ames mutagenesis - 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7531 75.31%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.6500 65.00%
skin sensitisation - 0.8896 88.96%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity - 0.7750 77.50%
Nephrotoxicity - 0.9290 92.90%
Acute Oral Toxicity (c) III 0.7434 74.34%
Estrogen receptor binding + 0.7940 79.40%
Androgen receptor binding + 0.7267 72.67%
Thyroid receptor binding - 0.5570 55.70%
Glucocorticoid receptor binding + 0.6584 65.84%
Aromatase binding + 0.6613 66.13%
PPAR gamma + 0.7704 77.04%
Honey bee toxicity - 0.6559 65.59%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6050 60.50%
Fish aquatic toxicity + 0.9174 91.74%

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 99.11% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.16% 96.09%
CHEMBL226 P30542 Adenosine A1 receptor 93.34% 95.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.14% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.74% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.62% 86.33%
CHEMBL1937 Q92769 Histone deacetylase 2 90.16% 94.75%
CHEMBL3714130 P46095 G-protein coupled receptor 6 89.25% 97.36%
CHEMBL2581 P07339 Cathepsin D 87.66% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.23% 95.89%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.49% 92.94%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.42% 97.25%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 84.71% 91.24%
CHEMBL221 P23219 Cyclooxygenase-1 84.18% 90.17%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 82.99% 95.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.72% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.05% 95.56%
CHEMBL2781 P19634 Sodium/hydrogen exchanger 1 80.51% 90.24%

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 16097918
LOTUS LTS0138776
wikiData Q105022257