(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,4R,6R)-6-hydroxy-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-4-yl]oxy]oxane-3,4,5-triol

Details

Top
Internal ID 1b26fbcf-2d1a-4184-8635-d2a9047ff554
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
IUPAC Name (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,4R,6R)-6-hydroxy-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-4-yl]oxy]oxane-3,4,5-triol
SMILES (Canonical) CC1(C2(CCC(O1)(C(C2)O)C)OC3C(C(C(C(O3)CO)O)O)O)C
SMILES (Isomeric) C[C@@]12CC[C@@](C[C@H]1O)(C(O2)(C)C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI InChI=1S/C16H28O8/c1-14(2)16(5-4-15(3,24-14)9(18)6-16)23-13-12(21)11(20)10(19)8(7-17)22-13/h8-13,17-21H,4-7H2,1-3H3/t8-,9-,10-,11+,12-,13+,15-,16-/m1/s1
InChI Key IQQCVQGVRVNZLT-WLEUBNQJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C16H28O8
Molecular Weight 348.39 g/mol
Exact Mass 348.17841785 g/mol
Topological Polar Surface Area (TPSA) 129.00 Ų
XlogP -1.40
Atomic LogP (AlogP) -1.35
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 3

Synonyms

Top
174285-77-9
(1R,4R,6R)-6-Hydroxy-1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-4-yl beta-D-glucopyranoside

2D Structure

Top
2D Structure of (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1R,4R,6R)-6-hydroxy-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-4-yl]oxy]oxane-3,4,5-triol

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6407 64.07%
Caco-2 - 0.7699 76.99%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7275 72.75%
OATP2B1 inhibitior - 0.8556 85.56%
OATP1B1 inhibitior + 0.9063 90.63%
OATP1B3 inhibitior + 0.8124 81.24%
MATE1 inhibitior - 0.9812 98.12%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior - 0.9257 92.57%
P-glycoprotein inhibitior - 0.8791 87.91%
P-glycoprotein substrate - 0.9249 92.49%
CYP3A4 substrate + 0.5976 59.76%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8411 84.11%
CYP3A4 inhibition - 0.9206 92.06%
CYP2C9 inhibition - 0.8812 88.12%
CYP2C19 inhibition - 0.9191 91.91%
CYP2D6 inhibition - 0.9610 96.10%
CYP1A2 inhibition - 0.9092 90.92%
CYP2C8 inhibition - 0.8133 81.33%
CYP inhibitory promiscuity - 0.9830 98.30%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.7187 71.87%
Eye corrosion - 0.9904 99.04%
Eye irritation - 0.9755 97.55%
Skin irritation - 0.7321 73.21%
Skin corrosion - 0.9602 96.02%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4907 49.07%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.7425 74.25%
skin sensitisation - 0.9187 91.87%
Respiratory toxicity - 0.5667 56.67%
Reproductive toxicity + 0.5333 53.33%
Mitochondrial toxicity - 0.6625 66.25%
Nephrotoxicity + 0.4808 48.08%
Acute Oral Toxicity (c) III 0.4768 47.68%
Estrogen receptor binding + 0.6425 64.25%
Androgen receptor binding - 0.5827 58.27%
Thyroid receptor binding + 0.7300 73.00%
Glucocorticoid receptor binding + 0.6737 67.37%
Aromatase binding + 0.7663 76.63%
PPAR gamma + 0.6433 64.33%
Honey bee toxicity - 0.8073 80.73%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.7800 78.00%
Fish aquatic toxicity + 0.7794 77.94%

Targets

Top

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.33% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 95.10% 91.11%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.42% 97.09%
CHEMBL218 P21554 Cannabinoid CB1 receptor 88.59% 96.61%
CHEMBL253 P34972 Cannabinoid CB2 receptor 85.77% 97.25%
CHEMBL1937 Q92769 Histone deacetylase 2 85.61% 94.75%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 85.00% 95.50%
CHEMBL226 P30542 Adenosine A1 receptor 82.92% 95.93%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.86% 86.92%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.62% 100.00%
CHEMBL2996 Q05655 Protein kinase C delta 82.56% 97.79%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 82.25% 96.21%
CHEMBL221 P23219 Cyclooxygenase-1 81.19% 90.17%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.69% 94.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.66% 95.89%
CHEMBL1907602 P06493 Cyclin-dependent kinase 1/cyclin B1 80.65% 91.24%

Plants that contains it

Top
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.
Foeniculum vulgare

Cross-Links

Top
PubChem 10712710
LOTUS LTS0035117
wikiData Q105118530