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(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9S,10R,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(E)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-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 6d04375f-5f8c-4c72-b164-e949ff97bd5d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9S,10R,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(E)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES (Canonical) CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)O)O)O)C)CO)OC(=O)C(=CC)C
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]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O)C)C)C)O)CO)(C)C)OC(=O)/C(=C/C)/C
InChI InChI=1S/C46H70O14/c1-11-23(3)38(55)59-35-36(60-39(56)24(4)12-2)46(22-48)26(19-41(35,5)6)25-13-14-28-42(7)17-16-30(57-40-33(52)31(50)32(51)34(58-40)37(53)54)43(8,21-47)27(42)15-18-44(28,9)45(25,10)20-29(46)49/h11-13,26-36,40,47-52H,14-22H2,1-10H3,(H,53,54)/b23-11+,24-12+/t26-,27+,28+,29-,30-,31-,32-,33+,34-,35-,36+,40+,42-,43-,44+,45+,46-/m0/s1
InChI Key HCTZEWPNCZGSAE-RLPAESDYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C46H70O14
Molecular Weight 847.00 g/mol
Exact Mass 846.47655690 g/mol
Topological Polar Surface Area (TPSA) 230.00 Ų
XlogP 5.60
Atomic LogP (AlogP) 3.98
H-Bond Acceptor 13
H-Bond Donor 7
Rotatable Bonds 9

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,4R,4aR,6aR,6bS,8S,8aR,9S,10R,12aS,14aR,14bR)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(E)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-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 + 0.8010 80.10%
Caco-2 - 0.8665 86.65%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.6857 68.57%
Subcellular localzation Mitochondria 0.8748 87.48%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8353 83.53%
OATP1B3 inhibitior - 0.3922 39.22%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5276 52.76%
BSEP inhibitior + 0.7608 76.08%
P-glycoprotein inhibitior + 0.7760 77.60%
P-glycoprotein substrate - 0.5702 57.02%
CYP3A4 substrate + 0.7255 72.55%
CYP2C9 substrate - 0.8018 80.18%
CYP2D6 substrate - 0.8966 89.66%
CYP3A4 inhibition - 0.7914 79.14%
CYP2C9 inhibition - 0.8443 84.43%
CYP2C19 inhibition - 0.8871 88.71%
CYP2D6 inhibition - 0.9429 94.29%
CYP1A2 inhibition - 0.8403 84.03%
CYP2C8 inhibition + 0.7506 75.06%
CYP inhibitory promiscuity - 0.9631 96.31%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6861 68.61%
Eye corrosion - 0.9899 98.99%
Eye irritation - 0.9064 90.64%
Skin irritation - 0.6003 60.03%
Skin corrosion - 0.9461 94.61%
Ames mutagenesis - 0.7548 75.48%
Human Ether-a-go-go-Related Gene inhibition + 0.6477 64.77%
Micronuclear - 0.7700 77.00%
Hepatotoxicity - 0.7642 76.42%
skin sensitisation - 0.8982 89.82%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity - 0.5000 50.00%
Nephrotoxicity + 0.7119 71.19%
Acute Oral Toxicity (c) III 0.8021 80.21%
Estrogen receptor binding + 0.7597 75.97%
Androgen receptor binding + 0.7470 74.70%
Thyroid receptor binding + 0.5233 52.33%
Glucocorticoid receptor binding + 0.7927 79.27%
Aromatase binding + 0.6554 65.54%
PPAR gamma + 0.8035 80.35%
Honey bee toxicity - 0.7337 73.37%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.6000 60.00%
Fish aquatic toxicity + 0.9649 96.49%

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 97.18% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.71% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 92.73% 90.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.39% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.59% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 90.46% 91.07%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.99% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.85% 99.17%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 86.84% 94.33%
CHEMBL2782 P35610 Acyl coenzyme A:cholesterol acyltransferase 1 86.78% 91.65%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.15% 86.33%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 85.74% 93.00%
CHEMBL5028 O14672 ADAM10 82.16% 97.50%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.08% 95.50%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.96% 89.00%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.04% 92.62%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.68% 100.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 80.60% 100.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 80.58% 97.36%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.56% 97.09%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 80.35% 95.50%

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.
Gymnema sylvestre

Cross-Links

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PubChem 102069190
LOTUS LTS0111952
wikiData Q105025993