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(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8S,8aS,10S,12aS,14aR,14bR)-10-benzoyloxy-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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 0a0018fe-da0f-4bb8-8f9f-960eff6afc81
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,10S,12aS,14aR,14bR)-10-benzoyloxy-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
SMILES (Canonical) CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CC(C2(CC1OC(=O)C6=CC=CC=C6)CO)O)C)C)(C)C)OC7C(C(C(C(O7)C(=O)O)O)OC8C(C(C(C(O8)CO)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@H](C5)OC(=O)C6=CC=CC=C6)(C)C)CO)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O
InChI InChI=1S/C49H72O16/c1-44(2)19-26-25-13-14-29-46(5)17-16-31(63-43-37(57)38(36(56)39(65-43)40(58)59)64-42-35(55)34(54)33(53)27(22-50)61-42)45(3,4)28(46)15-18-47(29,6)48(25,7)20-30(52)49(26,23-51)21-32(44)62-41(60)24-11-9-8-10-12-24/h8-13,26-39,42-43,50-57H,14-23H2,1-7H3,(H,58,59)/t26-,27+,28-,29+,30-,31-,32-,33+,34-,35+,36-,37+,38-,39-,42-,43+,46-,47+,48+,49+/m0/s1
InChI Key BCXIIRGZVLQKIH-HUZAOJMMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C49H72O16
Molecular Weight 917.10 g/mol
Exact Mass 916.48203620 g/mol
Topological Polar Surface Area (TPSA) 262.00 Ų
XlogP 4.90
Atomic LogP (AlogP) 2.69
H-Bond Acceptor 15
H-Bond Donor 9
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,4aR,6aR,6bS,8S,8aS,10S,12aS,14aR,14bR)-10-benzoyloxy-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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 + 0.8071 80.71%
Caco-2 - 0.8731 87.31%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.8508 85.08%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7639 76.39%
OATP1B3 inhibitior - 0.4332 43.32%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.5776 57.76%
BSEP inhibitior + 0.8815 88.15%
P-glycoprotein inhibitior + 0.7505 75.05%
P-glycoprotein substrate - 0.5948 59.48%
CYP3A4 substrate + 0.7372 73.72%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8822 88.22%
CYP3A4 inhibition - 0.6485 64.85%
CYP2C9 inhibition - 0.8438 84.38%
CYP2C19 inhibition - 0.8858 88.58%
CYP2D6 inhibition - 0.9350 93.50%
CYP1A2 inhibition - 0.8417 84.17%
CYP2C8 inhibition + 0.8248 82.48%
CYP inhibitory promiscuity - 0.9590 95.90%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6075 60.75%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9031 90.31%
Skin irritation - 0.6315 63.15%
Skin corrosion - 0.9465 94.65%
Ames mutagenesis - 0.6824 68.24%
Human Ether-a-go-go-Related Gene inhibition + 0.7471 74.71%
Micronuclear - 0.7600 76.00%
Hepatotoxicity - 0.7939 79.39%
skin sensitisation - 0.8967 89.67%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.9000 90.00%
Mitochondrial toxicity - 0.6000 60.00%
Nephrotoxicity - 0.8079 80.79%
Acute Oral Toxicity (c) III 0.7534 75.34%
Estrogen receptor binding + 0.7769 77.69%
Androgen receptor binding + 0.7513 75.13%
Thyroid receptor binding + 0.5505 55.05%
Glucocorticoid receptor binding + 0.7673 76.73%
Aromatase binding + 0.5962 59.62%
PPAR gamma + 0.8034 80.34%
Honey bee toxicity - 0.6925 69.25%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9824 98.24%

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
CHEMBL221 P23219 Cyclooxygenase-1 97.39% 90.17%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.47% 86.33%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.42% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.68% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.58% 95.56%
CHEMBL2581 P07339 Cathepsin D 89.14% 98.95%
CHEMBL5028 O14672 ADAM10 88.99% 97.50%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 87.20% 89.44%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 86.04% 94.08%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.88% 99.17%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 85.51% 94.62%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.05% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.66% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.59% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.14% 100.00%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.69% 96.21%
CHEMBL4302 P08183 P-glycoprotein 1 82.06% 92.98%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 80.34% 94.23%

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 21592400
LOTUS LTS0228708
wikiData Q104923695