2-Phenylethyl beta-primeveroside

Details

• Internal ID: 21e34ef5-473b-4c60-b6b4-1540e76763c1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2R,3R,4S,5S,6R)-2-(2-phenylethoxy)-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C(O1)OCC2C(C(C(C(O2)OCCC3=CC=CC=C3)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OCCC3=CC=CC=C3)O)O)O)O)O)O
• InChI: InChI=1S/C19H28O10/c20-11-8-27-18(16(24)13(11)21)28-9-12-14(22)15(23)17(25)19(29-12)26-7-6-10-4-2-1-3-5-10/h1-5,11-25H,6-9H2/t11-,12-,13+,14-,15+,16-,17-,18+,19-/m1/s1
• InChI Key: ZRGXCWYRIBRSQA-BMVMOQKNSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₁₀
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.16824709 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.49
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• PAXGP
• 129932-48-5
• Phenethyl alcohol xylopyranosyl-(1-6)-glucopyranoside
• (2R,3R,4S,5S,6R)-2-(2-phenylethoxy)-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• 2-phenylethyl 6-O-beta-D-xylopyranosyl-beta-D-glucopyranoside
• 2-Phenylethyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside
• (2R,3R,4S,5S,6R)-2-Phenethoxy-6-((((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triol
• SCHEMBL21853659
• DTXSID30156266
• CHEBI:136550
• C19H28O10
• C19-H28-O10
• beta-D-Xyl-(1->6)-beta-D-Glc-OCH2CH2Ph
• phenethyl beta-D-xylosyl-(1->6)-beta-D-glucoside
• 2-phenylethyl beta-D-xylosyl-(1->6)-beta-D-glucoside
• beta-D-Glucopyranoside, 2-phenylethyl 6-O-beta-D-xylopyranosyl
• 2-phenylethyl beta-D-xylopyranosyl-(1->6)-beta-D-glucopyranoside
• phenethyl alcohol beta-d-xylopyranosyl-(1-6)-beta-d-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9226	92.26%
Caco-2	-	0.8263	82.63%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8042	80.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9161	91.61%
OATP1B3 inhibitior	+	0.9272	92.72%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7291	72.91%
P-glycoprotein inhibitior	-	0.8369	83.69%
P-glycoprotein substrate	-	0.8712	87.12%
CYP3A4 substrate	+	0.5338	53.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7727	77.27%
CYP3A4 inhibition	-	0.9555	95.55%
CYP2C9 inhibition	-	0.9162	91.62%
CYP2C19 inhibition	-	0.8913	89.13%
CYP2D6 inhibition	-	0.9232	92.32%
CYP1A2 inhibition	-	0.9427	94.27%
CYP2C8 inhibition	-	0.5658	56.58%
CYP inhibitory promiscuity	-	0.9544	95.44%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6430	64.30%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9378	93.78%
Skin irritation	-	0.8469	84.69%
Skin corrosion	-	0.9680	96.80%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7046	70.46%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.8069	80.69%
skin sensitisation	-	0.9076	90.76%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9379	93.79%
Acute Oral Toxicity (c)	III	0.6076	60.76%
Estrogen receptor binding	+	0.5939	59.39%
Androgen receptor binding	-	0.7197	71.97%
Thyroid receptor binding	+	0.5765	57.65%
Glucocorticoid receptor binding	-	0.6137	61.37%
Aromatase binding	+	0.6959	69.59%
PPAR gamma	+	0.7448	74.48%
Honey bee toxicity	-	0.8208	82.08%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	-	0.6540	65.40%

Targets

Proven Targets:

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	97.07%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.80%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.69%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.00%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.76%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	87.02%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	86.90%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	84.64%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.41%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.28%	97.25%
CHEMBL3891	P07384	Calpain 1	82.65%	93.04%
CHEMBL5957	P21589	5'-nucleotidase	82.23%	97.78%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.42%	96.25%

Plants that contains it

• Alangium chinense
• Alangium platanifolium
• Camellia sinensis
• Helichrysum arenarium
• Jasminum sambac
• Rhodiola crenulata
• Stachys byzantina

Cross-Links

• PubChem: 131129
• NPASS: NPC84434
• LOTUS: LTS0238844
• wikiData: Q83024312