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(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8,10-trihydroxy-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]-3,4-dihydroxy-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid

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 3d2e99c5-7e86-41f7-a4c9-4b5422c33b71
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,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8,10-trihydroxy-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]-3,4-dihydroxy-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC=C(C)C(=O)OC1C(C(CC2C1(C(C(C3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)O)OC7C(C(C(C(O7)C)O)O)O)C)C)C)O)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@@H]([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)O[C@@H]7[C@H]([C@H]([C@@H]([C@H](O7)C)O)O)O)C)C)C)O)O)CO)(C)C)O
InChI InChI=1S/C47H74O17/c1-11-20(2)39(59)64-37-36(56)42(4,5)18-23-22-12-13-25-44(8)16-15-26(43(6,7)24(44)14-17-45(25,9)46(22,10)34(54)35(55)47(23,37)19-48)61-41-33(30(52)29(51)32(62-41)38(57)58)63-40-31(53)28(50)27(49)21(3)60-40/h11-12,21,23-37,40-41,48-56H,13-19H2,1-10H3,(H,57,58)/b20-11-/t21-,23+,24+,25-,26+,27-,28+,29+,30+,31+,32+,33-,34+,35-,36+,37+,40-,41-,44+,45-,46+,47+/m1/s1
InChI Key XXVNQOOHCDAFKO-YTINUVENSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C47H74O17
Molecular Weight 911.10 g/mol
Exact Mass 910.49260089 g/mol
Topological Polar Surface Area (TPSA) 283.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 1.31
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,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8,10-trihydroxy-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]-3,4-dihydroxy-5-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-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 + 0.7941 79.41%
Caco-2 - 0.8808 88.08%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.8948 89.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7867 78.67%
OATP1B3 inhibitior - 0.5056 50.56%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior + 0.6474 64.74%
BSEP inhibitior + 0.7335 73.35%
P-glycoprotein inhibitior + 0.7569 75.69%
P-glycoprotein substrate + 0.5000 50.00%
CYP3A4 substrate + 0.7328 73.28%
CYP2C9 substrate - 0.8018 80.18%
CYP2D6 substrate - 0.8966 89.66%
CYP3A4 inhibition - 0.8459 84.59%
CYP2C9 inhibition - 0.8380 83.80%
CYP2C19 inhibition - 0.9220 92.20%
CYP2D6 inhibition - 0.9493 94.93%
CYP1A2 inhibition - 0.8499 84.99%
CYP2C8 inhibition + 0.7583 75.83%
CYP inhibitory promiscuity - 0.9381 93.81%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6298 62.98%
Eye corrosion - 0.9898 98.98%
Eye irritation - 0.9050 90.50%
Skin irritation - 0.5723 57.23%
Skin corrosion - 0.9450 94.50%
Ames mutagenesis - 0.8078 80.78%
Human Ether-a-go-go-Related Gene inhibition + 0.6938 69.38%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.7814 78.14%
skin sensitisation - 0.9064 90.64%
Respiratory toxicity - 0.5778 57.78%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity - 0.6125 61.25%
Nephrotoxicity - 0.8050 80.50%
Acute Oral Toxicity (c) III 0.7628 76.28%
Estrogen receptor binding + 0.7861 78.61%
Androgen receptor binding + 0.7477 74.77%
Thyroid receptor binding - 0.5104 51.04%
Glucocorticoid receptor binding + 0.7593 75.93%
Aromatase binding + 0.6381 63.81%
PPAR gamma + 0.8040 80.40%
Honey bee toxicity - 0.6857 68.57%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity + 0.5200 52.00%
Fish aquatic toxicity + 0.9778 97.78%

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 98.30% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.27% 96.09%
CHEMBL221 P23219 Cyclooxygenase-1 94.84% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.10% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.34% 95.56%
CHEMBL3714130 P46095 G-protein coupled receptor 6 90.63% 97.36%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.60% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.08% 89.00%
CHEMBL2581 P07339 Cathepsin D 87.91% 98.95%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.11% 91.07%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.41% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.84% 100.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.65% 99.17%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.19% 93.00%
CHEMBL4208 P20618 Proteasome component C5 80.76% 90.00%

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.
Eryngium campestre

Cross-Links

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PubChem 44583928
LOTUS LTS0268877
wikiData Q105344225