Eugenol gentiobioside

Details

• Internal ID: fcf8e05b-45de-4398-88f5-a1b60eb28fb9
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-methoxy-4-prop-2-enylphenoxy)oxan-2-yl]methoxy]oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)CC=C)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)CC=C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
• InChI: InChI=1S/C22H32O12/c1-3-4-10-5-6-11(12(7-10)30-2)32-22-20(29)18(27)16(25)14(34-22)9-31-21-19(28)17(26)15(24)13(8-23)33-21/h3,5-7,13-29H,1,4,8-9H2,2H3/t13-,14-,15-,16-,17+,18+,19-,20-,21-,22-/m1/s1
• InChI Key: WXQNHYCVTYUIEE-OALZDZJCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₁₂
• Molecular Weight: 488.50 g/mol
• Exact Mass: 488.18937645 g/mol
• Topological Polar Surface Area (TPSA): 188.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.57
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

• AKOS040735972
• 2-Methoxy-4-[2-propenyl]phenyl 6-O-beta-D-glucopyranosyl-beta-D-glucopyranoside
• 134449-61-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8286	82.86%
Caco-2	-	0.8721	87.21%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5458	54.58%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8519	85.19%
OATP1B3 inhibitior	+	0.9758	97.58%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6525	65.25%
P-glycoprotein inhibitior	-	0.7428	74.28%
P-glycoprotein substrate	-	0.7560	75.60%
CYP3A4 substrate	+	0.5624	56.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7725	77.25%
CYP3A4 inhibition	-	0.7999	79.99%
CYP2C9 inhibition	-	0.8696	86.96%
CYP2C19 inhibition	-	0.8238	82.38%
CYP2D6 inhibition	-	0.8947	89.47%
CYP1A2 inhibition	-	0.9130	91.30%
CYP2C8 inhibition	+	0.7175	71.75%
CYP inhibitory promiscuity	-	0.6620	66.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6574	65.74%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9589	95.89%
Skin irritation	-	0.8291	82.91%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7137	71.37%
Micronuclear	-	0.5741	57.41%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.7940	79.40%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.7988	79.88%
Acute Oral Toxicity (c)	III	0.7235	72.35%
Estrogen receptor binding	+	0.6340	63.40%
Androgen receptor binding	-	0.7818	78.18%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5782	57.82%
Aromatase binding	+	0.6878	68.78%
PPAR gamma	+	0.6588	65.88%
Honey bee toxicity	-	0.7311	73.11%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.6885	68.85%

Targets

Proven Targets:

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	97.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.47%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.01%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.50%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.25%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	86.61%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.87%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.83%	86.92%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.61%	97.88%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.48%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.85%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.91%	92.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.81%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.31%	96.00%
CHEMBL4208	P20618	Proteasome component C5	80.15%	90.00%

Plants that contains it

• Allium sativum
• Aniba megaphylla
• Berberis integerrima
• Calocedrus decurrens
• Digitalis sceptrum
• Herbertus sakuraii
• Nauclea latifolia
• Orthopappus angustifolius
• Scurrula parasitica

Cross-Links

• PubChem: 10390778
• NPASS: NPC98593