(2R,3S,4S,5R,6S)-2-[[(2R,3R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-(4-hydroxy-3,5-dimethoxyphenoxy)oxane-3,4,5-triol

Details

• Internal ID: 806fb187-dde9-497b-8a39-3be53ff396e7
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-2-[[(2R,3R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-(4-hydroxy-3,5-dimethoxyphenoxy)oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)OC2C(C(C(C(O2)COC3C(C(CO3)(CO)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H](C(CO3)(CO)O)O)O)O)O
• InChI: InChI=1S/C19H28O13/c1-27-9-3-8(4-10(28-2)12(9)21)31-17-15(24)14(23)13(22)11(32-17)5-29-18-16(25)19(26,6-20)7-30-18/h3-4,11,13-18,20-26H,5-7H2,1-2H3/t11-,13-,14+,15-,16+,17-,18-,19?/m1/s1
• InChI Key: BPSJMBKZSUTYNF-YFDGBNAXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₁₃
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.15299094 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.95
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7416	74.16%
Caco-2	-	0.8637	86.37%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6794	67.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9028	90.28%
OATP1B3 inhibitior	+	0.9566	95.66%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7729	77.29%
P-glycoprotein inhibitior	-	0.7147	71.47%
P-glycoprotein substrate	-	0.6567	65.67%
CYP3A4 substrate	+	0.6073	60.73%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.8097	80.97%
CYP3A4 inhibition	-	0.9082	90.82%
CYP2C9 inhibition	-	0.8872	88.72%
CYP2C19 inhibition	-	0.8506	85.06%
CYP2D6 inhibition	-	0.9048	90.48%
CYP1A2 inhibition	-	0.8688	86.88%
CYP2C8 inhibition	+	0.4833	48.33%
CYP inhibitory promiscuity	-	0.8040	80.40%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9336	93.36%
Skin irritation	-	0.8339	83.39%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4083	40.83%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8434	84.34%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.7554	75.54%
Acute Oral Toxicity (c)	III	0.6898	68.98%
Estrogen receptor binding	+	0.7083	70.83%
Androgen receptor binding	-	0.6112	61.12%
Thyroid receptor binding	+	0.6391	63.91%
Glucocorticoid receptor binding	+	0.5765	57.65%
Aromatase binding	+	0.7335	73.35%
PPAR gamma	+	0.6677	66.77%
Honey bee toxicity	-	0.8490	84.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.5316	53.16%

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	99.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.02%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.28%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.64%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	92.95%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.78%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.86%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.82%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.75%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.72%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.17%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.91%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.29%	92.62%
CHEMBL4208	P20618	Proteasome component C5	84.74%	90.00%
CHEMBL4581	P52732	Kinesin-like protein 1	83.91%	93.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.40%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.33%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.62%	89.62%

Plants that contains it

• Canthium berberidifolium

Cross-Links

• PubChem: 6324881
• NPASS: NPC226640