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(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8S,8aR,9S,12aS,14aR,14bR)-9-acetyloxy-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-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 92720f5b-3931-488f-9262-a9b65c4e22cd
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,8S,8aR,9S,12aS,14aR,14bR)-9-acetyloxy-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-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) CC1C(C(C(C(O1)OCC23C(CC(CC2OC(=O)C)(C)C)C4=CCC5C6(CCC(C(C6CCC5(C4(CC3O)C)C)(C)C)OC7C(C(C(C(O7)C(=O)O)O)O)O)C)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@]23[C@H](C[C@@]4(C(=CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)C)C)[C@@H]2CC(C[C@@H]3OC(=O)C)(C)C)C)O)O)O)O
InChI InChI=1S/C44H70O15/c1-20-29(47)30(48)33(51)37(56-20)55-19-44-23(16-39(3,4)18-28(44)57-21(2)45)22-10-11-25-41(7)14-13-27(58-38-34(52)31(49)32(50)35(59-38)36(53)54)40(5,6)24(41)12-15-42(25,8)43(22,9)17-26(44)46/h10,20,23-35,37-38,46-52H,11-19H2,1-9H3,(H,53,54)/t20-,23-,24-,25+,26-,27-,28-,29-,30+,31-,32-,33+,34+,35-,37+,38+,41-,42+,43+,44-/m0/s1
InChI Key KDXSYGCLDPLGBO-LGCIVVFFSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C44H70O15
Molecular Weight 839.00 g/mol
Exact Mass 838.47147152 g/mol
Topological Polar Surface Area (TPSA) 242.00 Ų
XlogP 3.40
Atomic LogP (AlogP) 2.42
H-Bond Acceptor 14
H-Bond Donor 8
Rotatable Bonds 7

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,8S,8aR,9S,12aS,14aR,14bR)-9-acetyloxy-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]-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 + 0.8575 85.75%
Caco-2 - 0.8782 87.82%
Blood Brain Barrier - 0.5750 57.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8802 88.02%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7351 73.51%
OATP1B3 inhibitior - 0.3086 30.86%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.5526 55.26%
BSEP inhibitior - 0.5452 54.52%
P-glycoprotein inhibitior + 0.7677 76.77%
P-glycoprotein substrate - 0.6501 65.01%
CYP3A4 substrate + 0.7154 71.54%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8876 88.76%
CYP3A4 inhibition - 0.8128 81.28%
CYP2C9 inhibition - 0.8455 84.55%
CYP2C19 inhibition - 0.9268 92.68%
CYP2D6 inhibition - 0.9477 94.77%
CYP1A2 inhibition - 0.8962 89.62%
CYP2C8 inhibition + 0.7484 74.84%
CYP inhibitory promiscuity - 0.9609 96.09%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6259 62.59%
Eye corrosion - 0.9903 99.03%
Eye irritation - 0.9068 90.68%
Skin irritation + 0.4896 48.96%
Skin corrosion - 0.9425 94.25%
Ames mutagenesis - 0.8454 84.54%
Human Ether-a-go-go-Related Gene inhibition + 0.6833 68.33%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.8944 89.44%
skin sensitisation - 0.8909 89.09%
Respiratory toxicity - 0.5333 53.33%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity - 0.8882 88.82%
Acute Oral Toxicity (c) III 0.6896 68.96%
Estrogen receptor binding + 0.6967 69.67%
Androgen receptor binding + 0.7262 72.62%
Thyroid receptor binding - 0.5649 56.49%
Glucocorticoid receptor binding + 0.7153 71.53%
Aromatase binding + 0.6462 64.62%
PPAR gamma + 0.7646 76.46%
Honey bee toxicity - 0.7055 70.55%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5045 50.45%
Fish aquatic toxicity + 0.9817 98.17%

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 96.90% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.37% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.63% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 91.51% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.07% 95.56%
CHEMBL5028 O14672 ADAM10 87.30% 97.50%
CHEMBL2581 P07339 Cathepsin D 85.46% 98.95%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 85.25% 89.44%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.02% 94.45%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.77% 93.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.44% 100.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.70% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.39% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 80.76% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 80.43% 97.36%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.07% 100.00%

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.
Gymnema sylvestre

Cross-Links

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PubChem 101948663
LOTUS LTS0236089
wikiData Q105139661