(2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-(3-methylbut-2-enoxy)oxane-3,4,5-triol

Details

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Internal ID cd3b2b31-728e-4d8d-80ec-7da5a2183f52
Taxonomy Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
IUPAC Name (2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-(3-methylbut-2-enoxy)oxane-3,4,5-triol
SMILES (Canonical) CC(=CCOC1C(C(C(C(O1)COC2C(C(CO2)(CO)O)O)O)O)O)C
SMILES (Isomeric) CC(=CCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@](CO2)(CO)O)O)O)O)O)C
InChI InChI=1S/C16H28O10/c1-8(2)3-4-23-14-12(20)11(19)10(18)9(26-14)5-24-15-13(21)16(22,6-17)7-25-15/h3,9-15,17-22H,4-7H2,1-2H3/t9-,10-,11+,12-,13+,14-,15-,16-/m1/s1
InChI Key IBDIFTBEAJHIPD-NOJQTOCASA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C16H28O10
Molecular Weight 380.39 g/mol
Exact Mass 380.16824709 g/mol
Topological Polar Surface Area (TPSA) 158.00 Ų
XlogP -2.30
Atomic LogP (AlogP) -2.77
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 7

Synonyms

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3-Methyl-2-buten-1-yl 6-O-D-apio-beta-D-furanosyl-beta-D-glucopyranoside
3-Methyl-2-butenyl 6-O-D-apio-beta-D-furanosyl-beta-D-glucopyranoside
198832-70-1

2D Structure

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2D Structure of (2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-(3-methylbut-2-enoxy)oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6500 65.00%
Caco-2 - 0.8031 80.31%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.7886 78.86%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9285 92.85%
OATP1B3 inhibitior + 0.9421 94.21%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior - 0.8155 81.55%
P-glycoprotein inhibitior - 0.8438 84.38%
P-glycoprotein substrate - 0.8671 86.71%
CYP3A4 substrate + 0.5746 57.46%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8579 85.79%
CYP3A4 inhibition - 0.9849 98.49%
CYP2C9 inhibition - 0.8932 89.32%
CYP2C19 inhibition - 0.8808 88.08%
CYP2D6 inhibition - 0.9148 91.48%
CYP1A2 inhibition - 0.8892 88.92%
CYP2C8 inhibition - 0.7902 79.02%
CYP inhibitory promiscuity - 0.8962 89.62%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6879 68.79%
Eye corrosion - 0.9887 98.87%
Eye irritation - 0.9498 94.98%
Skin irritation - 0.7961 79.61%
Skin corrosion - 0.9488 94.88%
Ames mutagenesis + 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4694 46.94%
Micronuclear - 0.8700 87.00%
Hepatotoxicity - 0.6308 63.08%
skin sensitisation - 0.8409 84.09%
Respiratory toxicity - 0.6778 67.78%
Reproductive toxicity + 0.5444 54.44%
Mitochondrial toxicity - 0.6750 67.50%
Nephrotoxicity + 0.5899 58.99%
Acute Oral Toxicity (c) III 0.4716 47.16%
Estrogen receptor binding + 0.5641 56.41%
Androgen receptor binding - 0.6868 68.68%
Thyroid receptor binding + 0.6305 63.05%
Glucocorticoid receptor binding - 0.5361 53.61%
Aromatase binding + 0.7081 70.81%
PPAR gamma + 0.7319 73.19%
Honey bee toxicity - 0.8435 84.35%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7500 75.00%
Fish aquatic toxicity - 0.3706 37.06%

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 98.07% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 96.55% 95.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.67% 97.09%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.76% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 85.95% 94.73%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.78% 94.45%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.33% 100.00%
CHEMBL4187 Q99250 Sodium channel protein type II alpha subunit 83.97% 95.50%
CHEMBL5957 P21589 5'-nucleotidase 81.98% 97.78%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.73% 95.89%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.43% 86.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 80.32% 92.94%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.13% 96.90%

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.
Atractylodes lancea
Bupleurum falcatum

Cross-Links

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PubChem 10786012
NPASS NPC241171
LOTUS LTS0133417
wikiData Q105036441