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(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-12-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,12,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,11,12a,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 92eab0da-9a5a-4ff1-8454-a47dc02d91b6
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,8aS,11R,12R,12aS,14aR,14bR)-12-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,12,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES (Canonical) CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(C(O6)C(=O)O)O)O)O)C)C)C2C1(C)O)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O
SMILES (Isomeric) C[C@@H]1CC[C@@]2(CC[C@@]3(C(=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@@H]2[C@]1(C)O)C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
InChI InChI=1S/C42H66O16/c1-19-9-14-42(36(53)58-34-29(49)26(46)25(45)21(17-43)55-34)16-15-39(4)20(32(42)41(19,6)54)7-8-23-37(2)12-11-24(38(3,18-44)22(37)10-13-40(23,39)5)56-35-30(50)27(47)28(48)31(57-35)33(51)52/h7,19,21-32,34-35,43-50,54H,8-18H2,1-6H3,(H,51,52)/t19-,21-,22-,23-,24+,25-,26+,27+,28+,29-,30-,31+,32-,34+,35-,37+,38+,39-,40-,41-,42+/m1/s1
InChI Key DROUAZJCVDKKRH-BNFNWNNASA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C42H66O16
Molecular Weight 827.00 g/mol
Exact Mass 826.43508601 g/mol
Topological Polar Surface Area (TPSA) 273.00 Ų
XlogP 1.60
Atomic LogP (AlogP) 0.35
H-Bond Acceptor 15
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,4R,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-12-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,12,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,11,12a,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 + 0.6512 65.12%
Caco-2 - 0.8818 88.18%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.8681 86.81%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8301 83.01%
OATP1B3 inhibitior - 0.3733 37.33%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior + 0.5452 54.52%
BSEP inhibitior + 0.5669 56.69%
P-glycoprotein inhibitior + 0.7497 74.97%
P-glycoprotein substrate - 0.6553 65.53%
CYP3A4 substrate + 0.7200 72.00%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8811 88.11%
CYP3A4 inhibition - 0.9116 91.16%
CYP2C9 inhibition - 0.9240 92.40%
CYP2C19 inhibition - 0.9287 92.87%
CYP2D6 inhibition - 0.9557 95.57%
CYP1A2 inhibition - 0.8761 87.61%
CYP2C8 inhibition + 0.7259 72.59%
CYP inhibitory promiscuity - 0.9598 95.98%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6152 61.52%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9079 90.79%
Skin irritation - 0.5790 57.90%
Skin corrosion - 0.9471 94.71%
Ames mutagenesis - 0.8000 80.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6790 67.90%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.7625 76.25%
skin sensitisation - 0.9261 92.61%
Respiratory toxicity - 0.5111 51.11%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity - 0.5500 55.00%
Nephrotoxicity - 0.8491 84.91%
Acute Oral Toxicity (c) III 0.6932 69.32%
Estrogen receptor binding + 0.7128 71.28%
Androgen receptor binding + 0.7419 74.19%
Thyroid receptor binding - 0.5963 59.63%
Glucocorticoid receptor binding + 0.6750 67.50%
Aromatase binding + 0.6175 61.75%
PPAR gamma + 0.7515 75.15%
Honey bee toxicity - 0.7438 74.38%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.9625 96.25%

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
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.36% 95.56%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.24% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.26% 96.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 91.61% 97.36%
CHEMBL2581 P07339 Cathepsin D 90.86% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.77% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 86.62% 86.33%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 86.35% 93.00%
CHEMBL5255 O00206 Toll-like receptor 4 84.94% 92.50%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 83.57% 91.07%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.80% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.67% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.64% 99.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.59% 89.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.60% 100.00%
CHEMBL5028 O14672 ADAM10 80.56% 97.50%

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.
Ilex rotunda

Cross-Links

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PubChem 162946519
LOTUS LTS0127489
wikiData Q104987549