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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,11R,12S,12aS,14S,14aR,14bS)-8,14-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-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 905ad26d-39ab-4e64-847e-e5b12ee9cb5c
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,11R,12S,12aS,14S,14aR,14bS)-8,14-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-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) CC1CCC2(C(CC3(C(=CC(C4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C)O)O)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(CO8)O)O)O)C)C)O)C2C1C)C)O)CO
SMILES (Isomeric) C[C@@H]1CC[C@@]2([C@@H](C[C@@]3(C(=C[C@@H]([C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)C)O)O)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)C)C)O)[C@@H]2[C@H]1C)C)O)CO
InChI InChI=1S/C47H78O17/c1-20-9-14-47(19-49)28(52)16-46(8)23(30(47)21(20)2)15-24(50)39-44(6)12-11-29(43(4,5)27(44)10-13-45(39,46)7)62-41-37(34(56)31(53)22(3)60-41)64-42-38(35(57)33(55)26(17-48)61-42)63-40-36(58)32(54)25(51)18-59-40/h15,20-22,24-42,48-58H,9-14,16-19H2,1-8H3/t20-,21+,22-,24+,25-,26-,27+,28-,29+,30+,31+,32+,33-,34+,35+,36-,37-,38-,39-,40+,41+,42+,44+,45-,46-,47+/m1/s1
InChI Key DVWGWTHVNBZXHK-WQLDGIPISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C47H78O17
Molecular Weight 915.10 g/mol
Exact Mass 914.52390102 g/mol
Topological Polar Surface Area (TPSA) 278.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 0.08
H-Bond Acceptor 17
H-Bond Donor 11
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,11R,12S,12aS,14S,14aR,14bS)-8,14-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-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 - 0.8969 89.69%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.7876 78.76%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7392 73.92%
OATP1B3 inhibitior - 0.4367 43.67%
MATE1 inhibitior - 0.9612 96.12%
OCT2 inhibitior - 0.5500 55.00%
BSEP inhibitior + 0.5726 57.26%
P-glycoprotein inhibitior + 0.7502 75.02%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7407 74.07%
CYP2C9 substrate - 0.8025 80.25%
CYP2D6 substrate - 0.8264 82.64%
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 + 0.7092 70.92%
CYP inhibitory promiscuity - 0.9600 96.00%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6252 62.52%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.9074 90.74%
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 + 0.7781 77.81%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.7052 70.52%
skin sensitisation - 0.8896 88.96%
Respiratory toxicity - 0.5778 57.78%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity - 0.7750 77.50%
Nephrotoxicity - 0.9269 92.69%
Acute Oral Toxicity (c) III 0.7434 74.34%
Estrogen receptor binding + 0.7884 78.84%
Androgen receptor binding + 0.7379 73.79%
Thyroid receptor binding - 0.5742 57.42%
Glucocorticoid receptor binding + 0.6339 63.39%
Aromatase binding + 0.6807 68.07%
PPAR gamma + 0.7648 76.48%
Honey bee toxicity - 0.6470 64.70%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5300 53.00%
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 98.47% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.63% 96.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 93.91% 97.36%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.93% 97.09%
CHEMBL226 P30542 Adenosine A1 receptor 89.86% 95.93%
CHEMBL1937 Q92769 Histone deacetylase 2 89.14% 94.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.80% 86.33%
CHEMBL1994 P08235 Mineralocorticoid receptor 87.03% 100.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 86.78% 92.94%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.84% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.80% 94.00%
CHEMBL221 P23219 Cyclooxygenase-1 83.20% 90.17%
CHEMBL3589 P55263 Adenosine kinase 83.19% 98.05%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.14% 95.89%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 81.86% 95.50%
CHEMBL2581 P07339 Cathepsin D 81.56% 98.95%

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 163050827
LOTUS LTS0124522
wikiData Q104990387