(2S,3R,4R,5R,6S)-2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-3-yl]oxy]-6-methyl-tetrahydropyran-3,4,5-triol

Details

• Internal ID: 0aad120c-2dde-46af-9833-6fd3fb6c67a0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-3-yl]oxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C21H22O10/c1-8-17(26)18(27)19(28)21(29-8)31-16-7-11-13(24)5-10(22)6-15(11)30-20(16)9-2-3-12(23)14(25)4-9/h2-6,8,17-19,21-28H,7H2,1H3/t8-,17-,18+,19+,21-/m0/s1
• InChI Key: LUGRJXSUUSMJEB-VWLKIGRWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₁₀
• Molecular Weight: 434.40 g/mol
• Exact Mass: 434.12129689 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8824	88.24%
Caco-2	-	0.7389	73.89%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5918	59.18%
OATP2B1 inhibitior	+	0.5716	57.16%
OATP1B1 inhibitior	+	0.9496	94.96%
OATP1B3 inhibitior	+	0.9249	92.49%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4796	47.96%
P-glycoprotein inhibitior	-	0.6827	68.27%
P-glycoprotein substrate	-	0.8051	80.51%
CYP3A4 substrate	+	0.5892	58.92%
CYP2C9 substrate	-	0.8036	80.36%
CYP2D6 substrate	-	0.8018	80.18%
CYP3A4 inhibition	-	0.8546	85.46%
CYP2C9 inhibition	-	0.6464	64.64%
CYP2C19 inhibition	-	0.5222	52.22%
CYP2D6 inhibition	-	0.9226	92.26%
CYP1A2 inhibition	-	0.8160	81.60%
CYP2C8 inhibition	+	0.7769	77.69%
CYP inhibitory promiscuity	+	0.5589	55.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4682	46.82%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.7636	76.36%
Skin irritation	-	0.7224	72.24%
Skin corrosion	-	0.9256	92.56%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4204	42.04%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	-	0.6591	65.91%
skin sensitisation	-	0.7940	79.40%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8534	85.34%
Acute Oral Toxicity (c)	III	0.4141	41.41%
Estrogen receptor binding	+	0.5956	59.56%
Androgen receptor binding	+	0.5787	57.87%
Thyroid receptor binding	+	0.7169	71.69%
Glucocorticoid receptor binding	+	0.6470	64.70%
Aromatase binding	-	0.5180	51.80%
PPAR gamma	+	0.7001	70.01%
Honey bee toxicity	-	0.8090	80.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5750	57.50%
Fish aquatic toxicity	+	0.9575	95.75%

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	99.17%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.63%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.99%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.40%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.09%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.01%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.11%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.05%	95.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.93%	97.36%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.36%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	87.74%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.16%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.89%	92.94%
CHEMBL4208	P20618	Proteasome component C5	86.69%	90.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.13%	93.65%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.93%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	85.69%	86.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.60%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.11%	99.23%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.14%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.98%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.46%	95.89%

Plants that contains it

• Archidendron clypearia

Cross-Links

• PubChem: 71588877
• LOTUS: LTS0037019
• wikiData: Q105157414