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(4aR,6aR,6aR,6bR,8aS,10S,12aS,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-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 e97cd9da-fb1a-4337-8333-eae18b6968f5
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (4aR,6aR,6aR,6bR,8aS,10S,12aS,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)COC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O)O)O)O)C)C)C2C1)C)C(=O)O)C
SMILES (Isomeric) C[C@@]12CC[C@@H](C([C@H]1CC[C@@]3([C@@H]2CC=C4[C@@]3(CC[C@]5([C@@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O[C@@H]6[C@@H]([C@H]([C@H]([C@@H](O6)CO[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)CO[C@@H]8[C@@H]([C@H]([C@H](CO8)O)O)O)O)O)O)O)O)O
InChI InChI=1S/C47H76O17/c1-42(2)14-16-47(41(57)58)17-15-45(6)22(23(47)18-42)8-9-28-44(5)12-11-29(43(3,4)27(44)10-13-46(28,45)7)64-40-37(56)34(53)32(51)26(63-40)21-61-39-36(55)33(52)31(50)25(62-39)20-60-38-35(54)30(49)24(48)19-59-38/h8,23-40,48-56H,9-21H2,1-7H3,(H,57,58)/t23-,24+,25+,26+,27-,28-,29+,30+,31+,32+,33-,34+,35-,36-,37-,38-,39-,40-,44-,45+,46-,47-/m1/s1
InChI Key SAPHLLAJXWRHLX-QZNIOXFBSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C47H76O17
Molecular Weight 913.10 g/mol
Exact Mass 912.50825095 g/mol
Topological Polar Surface Area (TPSA) 275.00 Ų
XlogP 1.70
Atomic LogP (AlogP) 1.35
H-Bond Acceptor 16
H-Bond Donor 10
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (4aR,6aR,6aR,6bR,8aS,10S,12aS,14bR)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-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 + 0.8271 82.71%
Caco-2 - 0.8854 88.54%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.8653 86.53%
OATP2B1 inhibitior - 0.8784 87.84%
OATP1B1 inhibitior + 0.7284 72.84%
OATP1B3 inhibitior - 0.4215 42.15%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6776 67.76%
BSEP inhibitior + 0.8117 81.17%
P-glycoprotein inhibitior + 0.7466 74.66%
P-glycoprotein substrate - 0.7568 75.68%
CYP3A4 substrate + 0.7171 71.71%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.9495 94.95%
CYP2C9 inhibition - 0.8812 88.12%
CYP2C19 inhibition - 0.8995 89.95%
CYP2D6 inhibition - 0.9413 94.13%
CYP1A2 inhibition - 0.8966 89.66%
CYP2C8 inhibition + 0.6469 64.69%
CYP inhibitory promiscuity - 0.9650 96.50%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6211 62.11%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9072 90.72%
Skin irritation - 0.5934 59.34%
Skin corrosion - 0.9470 94.70%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7793 77.93%
Micronuclear - 0.8500 85.00%
Hepatotoxicity - 0.9125 91.25%
skin sensitisation - 0.8767 87.67%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity - 0.7000 70.00%
Nephrotoxicity - 0.8994 89.94%
Acute Oral Toxicity (c) III 0.7349 73.49%
Estrogen receptor binding + 0.7971 79.71%
Androgen receptor binding + 0.7196 71.96%
Thyroid receptor binding - 0.5480 54.80%
Glucocorticoid receptor binding + 0.6722 67.22%
Aromatase binding + 0.6433 64.33%
PPAR gamma + 0.7779 77.79%
Honey bee toxicity - 0.7554 75.54%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity - 0.6105 61.05%
Fish aquatic toxicity + 0.9671 96.71%

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 97.01% 91.11%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 96.83% 95.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.63% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.72% 97.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.16% 94.45%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 89.97% 96.77%
CHEMBL221 P23219 Cyclooxygenase-1 89.24% 90.17%
CHEMBL5255 O00206 Toll-like receptor 4 86.65% 92.50%
CHEMBL2581 P07339 Cathepsin D 86.59% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.81% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.81% 86.33%
CHEMBL5028 O14672 ADAM10 82.90% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.95% 95.89%

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 162986385
LOTUS LTS0202397
wikiData Q105249029