4-[4-hydroxy-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]butan-2-one

Details

• Internal ID: af04a4a5-1d99-43bc-9d83-963fda5526aa
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 4-[4-hydroxy-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]butan-2-one
• SMILES (Canonical): CC(=O)CCC1=CC(=C(C=C1)O)OC2C(C(C(C(O2)CO)O)O)O
• SMILES (Isomeric): CC(=O)CCC1=CC(=C(C=C1)O)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)CO)O)O)O
• InChI: InChI=1S/C16H22O8/c1-8(18)2-3-9-4-5-10(19)11(6-9)23-16-15(22)14(21)13(20)12(7-17)24-16/h4-6,12-17,19-22H,2-3,7H2,1H3/t12-,13-,14+,15-,16-/m0/s1
• InChI Key: LMPCSMHAJDXHSV-QMHWVQJVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₈
• Molecular Weight: 342.34 g/mol
• Exact Mass: 342.13146766 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -0.91
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5384	53.84%
Caco-2	-	0.8934	89.34%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8087	80.87%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9036	90.36%
OATP1B3 inhibitior	+	0.9244	92.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8379	83.79%
P-glycoprotein inhibitior	-	0.9460	94.60%
P-glycoprotein substrate	-	0.8758	87.58%
CYP3A4 substrate	+	0.5325	53.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8365	83.65%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.6344	63.44%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9131	91.31%
CYP1A2 inhibition	-	0.7201	72.01%
CYP2C8 inhibition	+	0.4879	48.79%
CYP inhibitory promiscuity	-	0.7749	77.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7481	74.81%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.8877	88.77%
Skin irritation	-	0.7550	75.50%
Skin corrosion	-	0.9474	94.74%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7593	75.93%
Micronuclear	-	0.8026	80.26%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8094	80.94%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.7798	77.98%
Acute Oral Toxicity (c)	III	0.7658	76.58%
Estrogen receptor binding	-	0.5063	50.63%
Androgen receptor binding	-	0.6586	65.86%
Thyroid receptor binding	-	0.5635	56.35%
Glucocorticoid receptor binding	-	0.4659	46.59%
Aromatase binding	-	0.5478	54.78%
PPAR gamma	+	0.6043	60.43%
Honey bee toxicity	-	0.8351	83.51%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6854	68.54%
Fish aquatic toxicity	+	0.8347	83.47%

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	99.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.31%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.84%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.07%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.15%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.49%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.55%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.80%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.21%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.34%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.13%	95.89%

Plants that contains it

• Baccharis dracunculifolia
• Vitex agnus-castus

Cross-Links

• PubChem: 101260815
• LOTUS: LTS0142798
• wikiData: Q105154097