[(2R,3S,4S,5R,6S)-4,5-dihydroxy-6-[4-hydroxy-2-[[(1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl]oxymethyl]phenoxy]-2-(hydroxymethyl)oxan-3-yl] benzoate

Details

• Internal ID: d78cb27d-6553-4f50-a370-ab258e3bf18c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-4,5-dihydroxy-6-[4-hydroxy-2-[[(1R)-1-hydroxy-6-oxocyclohex-2-ene-1-carbonyl]oxymethyl]phenoxy]-2-(hydroxymethyl)oxan-3-yl] benzoate
• SMILES (Canonical): C1CC(=O)C(C=C1)(C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)CO)OC(=O)C4=CC=CC=C4)O)O)O
• SMILES (Isomeric): C1CC(=O)[C@](C=C1)(C(=O)OCC2=C(C=CC(=C2)O)O[C@H]3[C@@H]([C@@H]([C@@H]([C@H](O3)CO)OC(=O)C4=CC=CC=C4)O)O)O
• InChI: InChI=1S/C27H28O12/c28-13-19-23(39-24(33)15-6-2-1-3-7-15)21(31)22(32)25(38-19)37-18-10-9-17(29)12-16(18)14-36-26(34)27(35)11-5-4-8-20(27)30/h1-3,5-7,9-12,19,21-23,25,28-29,31-32,35H,4,8,13-14H2/t19-,21+,22-,23-,25-,27-/m1/s1
• InChI Key: XBIKYSOVRUWWOS-GYARYYMISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₁₂
• Molecular Weight: 544.50 g/mol
• Exact Mass: 544.15807632 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5410	54.10%
Caco-2	-	0.8929	89.29%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8435	84.35%
OATP2B1 inhibitior	-	0.8463	84.63%
OATP1B1 inhibitior	+	0.8724	87.24%
OATP1B3 inhibitior	+	0.9501	95.01%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5763	57.63%
P-glycoprotein inhibitior	+	0.6580	65.80%
P-glycoprotein substrate	-	0.6540	65.40%
CYP3A4 substrate	+	0.6704	67.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.8539	85.39%
CYP2C9 inhibition	-	0.5791	57.91%
CYP2C19 inhibition	-	0.6897	68.97%
CYP2D6 inhibition	-	0.9215	92.15%
CYP1A2 inhibition	-	0.8328	83.28%
CYP2C8 inhibition	+	0.7430	74.30%
CYP inhibitory promiscuity	-	0.8655	86.55%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6269	62.69%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.8453	84.53%
Skin corrosion	-	0.9486	94.86%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6267	62.67%
Hepatotoxicity	-	0.5927	59.27%
skin sensitisation	-	0.8342	83.42%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6648	66.48%
Acute Oral Toxicity (c)	III	0.6273	62.73%
Estrogen receptor binding	+	0.7374	73.74%
Androgen receptor binding	+	0.7255	72.55%
Thyroid receptor binding	-	0.5806	58.06%
Glucocorticoid receptor binding	+	0.6134	61.34%
Aromatase binding	+	0.5879	58.79%
PPAR gamma	+	0.6216	62.16%
Honey bee toxicity	-	0.7689	76.89%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.8930	89.30%

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	98.84%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.63%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.93%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.10%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.89%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.94%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.81%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.65%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.08%	94.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.63%	83.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.48%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.64%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.81%	91.07%
CHEMBL4208	P20618	Proteasome component C5	84.72%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.86%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.83%	92.62%
CHEMBL3891	P07384	Calpain 1	83.70%	93.04%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.69%	94.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.21%	95.83%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.15%	97.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.93%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.88%	94.62%

Plants that contains it

• Itoa orientalis

Cross-Links

• PubChem: 163026484
• LOTUS: LTS0161382
• wikiData: Q105324504