[(3R,4S,5R)-5-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl furan-2-carboxylate

Details

• Internal ID: 089ddb8c-1707-4916-8b12-dc157c190791
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(3R,4S,5R)-5-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl furan-2-carboxylate
• SMILES (Canonical): C1C(C(C(O1)OC2C(C(C(OC2OC3=CC=C(C=C3)O)CO)O)O)O)(COC(=O)C4=CC=CO4)O
• SMILES (Isomeric): C1[C@]([C@@H]([C@H](O1)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2OC3=CC=C(C=C3)O)CO)O)O)O)(COC(=O)C4=CC=CO4)O
• InChI: InChI=1S/C22H26O13/c23-8-14-15(25)16(26)17(20(34-14)33-12-5-3-11(24)4-6-12)35-21-18(27)22(29,10-32-21)9-31-19(28)13-2-1-7-30-13/h1-7,14-18,20-21,23-27,29H,8-10H2/t14-,15-,16+,17-,18+,20-,21+,22-/m0/s1
• InChI Key: OOMRRHXBUCKSRD-ASRPDNLVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆O₁₃
• Molecular Weight: 498.40 g/mol
• Exact Mass: 498.13734088 g/mol
• Topological Polar Surface Area (TPSA): 198.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.51
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7539	75.39%
Caco-2	-	0.8832	88.32%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7112	71.12%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.8855	88.55%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5424	54.24%
P-glycoprotein inhibitior	-	0.6083	60.83%
P-glycoprotein substrate	-	0.7119	71.19%
CYP3A4 substrate	+	0.6834	68.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8615	86.15%
CYP3A4 inhibition	-	0.8641	86.41%
CYP2C9 inhibition	-	0.9188	91.88%
CYP2C19 inhibition	-	0.8982	89.82%
CYP2D6 inhibition	-	0.9064	90.64%
CYP1A2 inhibition	-	0.9280	92.80%
CYP2C8 inhibition	+	0.6437	64.37%
CYP inhibitory promiscuity	-	0.8069	80.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5514	55.14%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9190	91.90%
Skin irritation	-	0.8319	83.19%
Skin corrosion	-	0.9578	95.78%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4362	43.62%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	-	0.7341	73.41%
skin sensitisation	-	0.8541	85.41%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.6901	69.01%
Acute Oral Toxicity (c)	III	0.6613	66.13%
Estrogen receptor binding	+	0.8233	82.33%
Androgen receptor binding	+	0.6141	61.41%
Thyroid receptor binding	+	0.5467	54.67%
Glucocorticoid receptor binding	+	0.5803	58.03%
Aromatase binding	+	0.7571	75.71%
PPAR gamma	+	0.7388	73.88%
Honey bee toxicity	-	0.7554	75.54%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.6407	64.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	98.95%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.93%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.37%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.97%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.60%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.99%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.72%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.06%	95.89%
CHEMBL4208	P20618	Proteasome component C5	86.99%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.19%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.53%	89.00%
CHEMBL2581	P07339	Cathepsin D	85.46%	98.95%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.91%	92.67%
CHEMBL221	P23219	Cyclooxygenase-1	84.83%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.39%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.71%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.34%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	80.77%	94.73%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.63%	94.00%

Plants that contains it

• Myrsine seguinii

Cross-Links

• PubChem: 163186912
• LOTUS: LTS0242417
• wikiData: Q105195481