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(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8aR,12S,12aS,14aR,14bR)-12-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,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 fefaaa70-fc76-475d-ab9a-ae57a17c5243
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
IUPAC Name (2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8aR,12S,12aS,14aR,14bR)-12-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES (Canonical) CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(C(O6)C(=O)O)O)O)O)C)C)C2C1O)C)C(=O)OC7C(C(C(C(O7)CO)O)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]4[C@@H](C(CC5)(C)C)O)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)CO)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O
InChI InChI=1S/C42H66O16/c1-37(2)13-15-42(36(54)58-34-29(49)26(46)25(45)20(17-43)55-34)16-14-40(5)19(24(42)32(37)51)7-8-22-38(3)11-10-23(39(4,18-44)21(38)9-12-41(22,40)6)56-35-30(50)27(47)28(48)31(57-35)33(52)53/h7,20-32,34-35,43-51H,8-18H2,1-6H3,(H,52,53)/t20-,21-,22-,23+,24-,25-,26+,27+,28+,29-,30-,31+,32+,34+,35-,38+,39+,40-,41-,42+/m1/s1
InChI Key PVRGMAUCVQOWGZ-DDJWYDGKSA-N
Popularity 1 reference 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 1.80
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,8aR,12S,12aS,14aR,14bR)-12-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,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 + 0.7181 71.81%
Caco-2 - 0.8843 88.43%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.8914 89.14%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8381 83.81%
OATP1B3 inhibitior - 0.5187 51.87%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior + 0.5974 59.74%
BSEP inhibitior - 0.5000 50.00%
P-glycoprotein inhibitior + 0.7511 75.11%
P-glycoprotein substrate - 0.7374 73.74%
CYP3A4 substrate + 0.7153 71.53%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8776 87.76%
CYP3A4 inhibition - 0.9061 90.61%
CYP2C9 inhibition - 0.8653 86.53%
CYP2C19 inhibition - 0.9130 91.30%
CYP2D6 inhibition - 0.9498 94.98%
CYP1A2 inhibition - 0.8749 87.49%
CYP2C8 inhibition + 0.7585 75.85%
CYP inhibitory promiscuity - 0.9549 95.49%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6115 61.15%
Eye corrosion - 0.9892 98.92%
Eye irritation - 0.9071 90.71%
Skin irritation - 0.6295 62.95%
Skin corrosion - 0.9453 94.53%
Ames mutagenesis - 0.7600 76.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7263 72.63%
Micronuclear - 0.7900 79.00%
Hepatotoxicity - 0.8000 80.00%
skin sensitisation - 0.9028 90.28%
Respiratory toxicity - 0.6444 64.44%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity - 0.6250 62.50%
Nephrotoxicity - 0.6471 64.71%
Acute Oral Toxicity (c) III 0.7689 76.89%
Estrogen receptor binding + 0.7302 73.02%
Androgen receptor binding + 0.7382 73.82%
Thyroid receptor binding - 0.5900 59.00%
Glucocorticoid receptor binding + 0.6881 68.81%
Aromatase binding + 0.6299 62.99%
PPAR gamma + 0.7590 75.90%
Honey bee toxicity - 0.7443 74.43%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9722 97.22%

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 96.84% 91.11%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.82% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.96% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 88.57% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 87.21% 97.36%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.83% 94.45%
CHEMBL3060 Q9Y345 Glycine transporter 2 84.59% 99.17%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 83.70% 93.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.58% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.51% 86.33%
CHEMBL237 P41145 Kappa opioid receptor 83.36% 98.10%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.31% 100.00%
CHEMBL5028 O14672 ADAM10 82.54% 97.50%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 82.50% 94.23%
CHEMBL2581 P07339 Cathepsin D 82.45% 98.95%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.12% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.68% 100.00%
CHEMBL5255 O00206 Toll-like receptor 4 81.31% 92.50%

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 101641960
LOTUS LTS0188595
wikiData Q105215569