(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,10-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

Details

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Internal ID eb468f7c-9c70-469e-bb7e-5bd129510101
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,10-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC=C(C)C(=O)OC1C(C(CC2C1(C(CC3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)O)CO)(C)C)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[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)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)O)CO)(C)C)O
InChI InChI=1S/C52H82O21/c1-10-22(2)43(66)73-41-40(63)47(3,4)17-24-23-11-12-28-49(7)15-14-30(48(5,6)27(49)13-16-50(28,8)51(23,9)18-29(56)52(24,41)21-54)69-46-39(72-45-35(61)33(59)32(58)26(19-53)68-45)37(36(62)38(71-46)42(64)65)70-44-34(60)31(57)25(55)20-67-44/h10-11,24-41,44-46,53-63H,12-21H2,1-9H3,(H,64,65)/b22-10-/t24-,25-,26+,27-,28+,29+,30-,31-,32+,33-,34+,35+,36-,37-,38-,39+,40-,41-,44-,45-,46+,49-,50+,51+,52-/m0/s1
InChI Key OMZNKQCPCUOTLS-WPYHJIHXSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C52H82O21
Molecular Weight 1043.20 g/mol
Exact Mass 1042.53485962 g/mol
Topological Polar Surface Area (TPSA) 342.00 Ų
XlogP 1.90
Atomic LogP (AlogP) -0.23
H-Bond Acceptor 20
H-Bond Donor 12
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,10-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7601 76.01%
Caco-2 - 0.8796 87.96%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7714 77.14%
Subcellular localzation Mitochondria 0.8703 87.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7374 73.74%
OATP1B3 inhibitior - 0.4610 46.10%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5026 50.26%
BSEP inhibitior + 0.9037 90.37%
P-glycoprotein inhibitior + 0.7507 75.07%
P-glycoprotein substrate - 0.5087 50.87%
CYP3A4 substrate + 0.7423 74.23%
CYP2C9 substrate - 0.8018 80.18%
CYP2D6 substrate - 0.8966 89.66%
CYP3A4 inhibition - 0.8310 83.10%
CYP2C9 inhibition - 0.8704 87.04%
CYP2C19 inhibition - 0.9216 92.16%
CYP2D6 inhibition - 0.9491 94.91%
CYP1A2 inhibition - 0.9009 90.09%
CYP2C8 inhibition + 0.7788 77.88%
CYP inhibitory promiscuity - 0.9733 97.33%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6024 60.24%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.9009 90.09%
Skin irritation - 0.5876 58.76%
Skin corrosion - 0.9441 94.41%
Ames mutagenesis - 0.7078 70.78%
Human Ether-a-go-go-Related Gene inhibition + 0.6986 69.86%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation - 0.9013 90.13%
Respiratory toxicity - 0.5889 58.89%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity - 0.6250 62.50%
Nephrotoxicity - 0.7692 76.92%
Acute Oral Toxicity (c) III 0.8023 80.23%
Estrogen receptor binding + 0.7844 78.44%
Androgen receptor binding + 0.7518 75.18%
Thyroid receptor binding + 0.5185 51.85%
Glucocorticoid receptor binding + 0.7830 78.30%
Aromatase binding + 0.5976 59.76%
PPAR gamma + 0.8165 81.65%
Honey bee toxicity - 0.6299 62.99%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9585 95.85%

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 98.15% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.07% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 94.46% 94.45%
CHEMBL1937 Q92769 Histone deacetylase 2 90.24% 94.75%
CHEMBL221 P23219 Cyclooxygenase-1 89.02% 90.17%
CHEMBL2581 P07339 Cathepsin D 88.74% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.24% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.65% 95.56%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 86.37% 93.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.61% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.06% 95.89%
CHEMBL5255 O00206 Toll-like receptor 4 84.27% 92.50%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.07% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 83.96% 94.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.78% 99.17%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 83.46% 95.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.98% 91.07%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.15% 95.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 82.02% 89.00%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 81.45% 89.67%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.45% 91.24%

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.
Eryngium yuccifolium

Cross-Links

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PubChem 162888493
LOTUS LTS0182468
wikiData Q105194549