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(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8S,8aS,9S,12aS,14aR,14bR)-8,9-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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 2ce39f8d-bdbc-40ed-bfae-31604ec735a1
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,8aS,9S,12aS,14aR,14bR)-8,9-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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) CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CC(C2(C(C1)O)COC6C(C(C(C(O6)CO)O)O)O)O)C)C)(C)C)OC7C(C(C(C(O7)C(=O)O)O)O)O)C)C
SMILES (Isomeric) C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@@H]([C@@]5([C@H]4CC(C[C@@H]5O)(C)C)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O
InChI InChI=1S/C42H68O15/c1-37(2)14-20-19-8-9-23-39(5)12-11-26(56-36-32(51)29(48)30(49)33(57-36)34(52)53)38(3,4)22(39)10-13-40(23,6)41(19,7)16-25(45)42(20,24(44)15-37)18-54-35-31(50)28(47)27(46)21(17-43)55-35/h8,20-33,35-36,43-51H,9-18H2,1-7H3,(H,52,53)/t20-,21+,22-,23+,24-,25-,26-,27+,28-,29-,30-,31+,32+,33-,35+,36+,39-,40+,41+,42+/m0/s1
InChI Key AVVLSVURAFVGRE-WLUYCGPPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C42H68O15
Molecular Weight 813.00 g/mol
Exact Mass 812.45582146 g/mol
Topological Polar Surface Area (TPSA) 256.00 Ų
XlogP 2.30
Atomic LogP (AlogP) 0.82
H-Bond Acceptor 14
H-Bond Donor 10
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,8aS,9S,12aS,14aR,14bR)-8,9-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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 + 0.7891 78.91%
Caco-2 - 0.8823 88.23%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8567 85.67%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7720 77.20%
OATP1B3 inhibitior - 0.5700 57.00%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.6276 62.76%
BSEP inhibitior - 0.5416 54.16%
P-glycoprotein inhibitior + 0.7566 75.66%
P-glycoprotein substrate - 0.8166 81.66%
CYP3A4 substrate + 0.7080 70.80%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8798 87.98%
CYP3A4 inhibition - 0.9300 93.00%
CYP2C9 inhibition - 0.8838 88.38%
CYP2C19 inhibition - 0.9101 91.01%
CYP2D6 inhibition - 0.9422 94.22%
CYP1A2 inhibition - 0.8933 89.33%
CYP2C8 inhibition + 0.7060 70.60%
CYP inhibitory promiscuity - 0.9668 96.68%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6254 62.54%
Eye corrosion - 0.9900 99.00%
Eye irritation - 0.9077 90.77%
Skin irritation - 0.6103 61.03%
Skin corrosion - 0.9480 94.80%
Ames mutagenesis - 0.8624 86.24%
Human Ether-a-go-go-Related Gene inhibition + 0.7251 72.51%
Micronuclear - 0.8600 86.00%
Hepatotoxicity - 0.9223 92.23%
skin sensitisation - 0.8917 89.17%
Respiratory toxicity - 0.5667 56.67%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity - 0.7625 76.25%
Nephrotoxicity - 0.8337 83.37%
Acute Oral Toxicity (c) III 0.7945 79.45%
Estrogen receptor binding + 0.6911 69.11%
Androgen receptor binding + 0.7266 72.66%
Thyroid receptor binding - 0.5742 57.42%
Glucocorticoid receptor binding + 0.6413 64.13%
Aromatase binding + 0.6319 63.19%
PPAR gamma + 0.7398 73.98%
Honey bee toxicity - 0.7473 74.73%
Biodegradation - 0.6750 67.50%
Crustacea aquatic toxicity - 0.5955 59.55%
Fish aquatic toxicity + 0.9411 94.11%

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 96.08% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.19% 96.09%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 91.93% 96.21%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.74% 95.56%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.74% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.45% 97.09%
CHEMBL221 P23219 Cyclooxygenase-1 86.66% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.62% 86.33%
CHEMBL5028 O14672 ADAM10 85.77% 97.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.56% 95.89%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 84.69% 93.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.83% 100.00%
CHEMBL2111367 P27986 PI3-kinase p110-alpha/p85-alpha 82.45% 94.33%
CHEMBL2581 P07339 Cathepsin D 82.17% 98.95%
CHEMBL5255 O00206 Toll-like receptor 4 81.89% 92.50%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.86% 100.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.69% 95.50%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.38% 99.17%

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 101948667
LOTUS LTS0170950
wikiData Q104919860