methyl 5-[(2R,3R,4R,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-2-hydroxybenzoate

Details

• Internal ID: d3d0c902-78c2-4e87-9580-a96a6737c465
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: methyl 5-[(2R,3R,4R,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-2-hydroxybenzoate
• SMILES (Canonical): COC(=O)C1=C(C=CC(=C1)OC2C(C(C(CO2)O)OC3C(C(CO3)(CO)O)O)O)O
• SMILES (Isomeric): COC(=O)C1=C(C=CC(=C1)O[C@@H]2[C@@H]([C@@H]([C@@H](CO2)O)O[C@H]3[C@@H]([C@](CO3)(CO)O)O)O)O
• InChI: InChI=1S/C18H24O12/c1-26-15(24)9-4-8(2-3-10(9)20)29-16-12(22)13(11(21)5-27-16)30-17-14(23)18(25,6-19)7-28-17/h2-4,11-14,16-17,19-23,25H,5-7H2,1H3/t11-,12-,13-,14+,16-,17+,18-/m1/s1
• InChI Key: RZVNYFCJWGTYBA-VQPYYTDLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₁₂
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.12677620 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.54
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6656	66.56%
Caco-2	-	0.8702	87.02%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6797	67.97%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.9173	91.73%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5208	52.08%
P-glycoprotein inhibitior	-	0.7564	75.64%
P-glycoprotein substrate	-	0.6147	61.47%
CYP3A4 substrate	+	0.6418	64.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.8586	85.86%
CYP2C9 inhibition	-	0.8806	88.06%
CYP2C19 inhibition	-	0.8661	86.61%
CYP2D6 inhibition	-	0.9101	91.01%
CYP1A2 inhibition	-	0.8912	89.12%
CYP2C8 inhibition	-	0.5863	58.63%
CYP inhibitory promiscuity	-	0.7833	78.33%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5674	56.74%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9363	93.63%
Skin irritation	-	0.8193	81.93%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4948	49.48%
Micronuclear	-	0.5367	53.67%
Hepatotoxicity	-	0.5177	51.77%
skin sensitisation	-	0.8337	83.37%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.6869	68.69%
Acute Oral Toxicity (c)	III	0.7621	76.21%
Estrogen receptor binding	+	0.7162	71.62%
Androgen receptor binding	-	0.5964	59.64%
Thyroid receptor binding	+	0.5412	54.12%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6533	65.33%
PPAR gamma	+	0.6626	66.26%
Honey bee toxicity	-	0.7714	77.14%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.6295	62.95%

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	99.58%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.36%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.07%	96.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.36%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	90.61%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.54%	91.24%
CHEMBL4208	P20618	Proteasome component C5	90.39%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.25%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	90.14%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.23%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	88.52%	91.49%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.36%	90.71%
CHEMBL2581	P07339	Cathepsin D	85.57%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.06%	97.09%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	84.99%	92.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.87%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.00%	91.19%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.23%	94.42%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.02%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.38%	92.94%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.38%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.96%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.35%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.25%	86.92%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.06%	95.17%

Plants that contains it

• Lindera neesiana

Cross-Links

• PubChem: 163029887
• LOTUS: LTS0241445
• wikiData: Q105248634