Arbutin

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	155c8a12-638d-4407-86a0-3cb53daa6e9f
Taxonomy	Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
IUPAC Name	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
SMILES (Canonical)	C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
SMILES (Isomeric)	C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
InChI	InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
InChI Key	BJRNKVDFDLYUGJ-RMPHRYRLSA-N
Popularity	3,264 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₂H₁₆O₇
Molecular Weight	272.25 g/mol
Exact Mass	272.08960285 g/mol
Topological Polar Surface Area (TPSA)	120.00 Å²
XlogP	-0.70
Atomic LogP (AlogP)	-1.43
H-Bond Acceptor	7
H-Bond Donor	5
Rotatable Bonds	3

Synonyms

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497-76-7

Arbutoside

Ursin

Uvasol

p-Arbutin

beta-Arbutin

4-Hydroxyphenyl beta-D-glucopyranoside

p-Hydroxyphenyl beta-D-glucoside

Arbutine

Arbutinum

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8477	84.77%
Caco-2	-	0.7795	77.95%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6581	65.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9783	97.83%
P-glycoprotein inhibitior	-	0.9527	95.27%
P-glycoprotein substrate	-	0.9829	98.29%
CYP3A4 substrate	-	0.5643	56.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.9064	90.64%
CYP2C9 inhibition	-	0.8842	88.42%
CYP2C19 inhibition	-	0.8964	89.64%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.9469	94.69%
CYP2C8 inhibition	-	0.6568	65.68%
CYP inhibitory promiscuity	-	0.7203	72.03%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6342	63.42%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8041	80.41%
Skin irritation	-	0.8321	83.21%
Skin corrosion	-	0.9712	97.12%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7132	71.32%
Micronuclear	-	0.6141	61.41%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8479	84.79%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	-	0.5333	53.33%
Mitochondrial toxicity	-	0.8500	85.00%
Nephrotoxicity	-	0.5599	55.99%
Acute Oral Toxicity (c)	III	0.6959	69.59%
Estrogen receptor binding	-	0.8407	84.07%
Androgen receptor binding	-	0.5375	53.75%
Thyroid receptor binding	-	0.5781	57.81%
Glucocorticoid receptor binding	-	0.6081	60.81%
Aromatase binding	-	0.7771	77.71%
PPAR gamma	+	0.5756	57.56%
Honey bee toxicity	-	0.8583	85.83%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	-	0.5310	53.10%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1973	P14679	Tyrosinase	230000 nM 30260 nM	IC50 IC50	PMID: 16872137 PMID: 17693086

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.11%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.12%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.11%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	89.62%	95.93%
CHEMBL242	Q92731	Estrogen receptor beta	88.41%	98.35%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.36%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.01%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	83.64%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.09%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.80%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.33%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.54%	86.92%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.16%	85.00%

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.

Antennaria microphylla

Anthemis cretica

Antiphiona pinnatisecta

Arbutus unedo

Arctostaphylos columbiana

Arctostaphylos uva-ursi

Artocarpus altilis