(2S,3R,4S,5S,6R)-2-[[(2S,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 559b5e06-24fe-4b33-a1c1-b8182afecf6b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(2S,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(OC2=CC(=CC(=C21)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)O)O
• SMILES (Isomeric): C1[C@H]([C@@H](OC2=CC(=CC(=C21)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC=C(C=C4)O)O
• InChI: InChI=1S/C21H24O10/c22-8-16-17(26)18(27)19(28)21(31-16)29-11-5-13(24)12-7-14(25)20(30-15(12)6-11)9-1-3-10(23)4-2-9/h1-6,14,16-28H,7-8H2/t14-,16-,17-,18+,19-,20+,21-/m1/s1
• InChI Key: BUZPALUBBJZNNV-ZZIZYRMTSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₁₀
• Molecular Weight: 436.40 g/mol
• Exact Mass: 436.13694696 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.69
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• CHEBI:182269
• AKOS040738336
• NCGC00384633-01
• (2S,3R,4S,5S,6R)-2-[[(2S,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• NCGC00384633-01_C21H24O10_(2S,3R)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-yl beta-D-threo-hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5547	55.47%
Caco-2	-	0.9148	91.48%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.4774	47.74%
OATP2B1 inhibitior	-	0.5768	57.68%
OATP1B1 inhibitior	+	0.7034	70.34%
OATP1B3 inhibitior	+	0.9229	92.29%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6772	67.72%
P-glycoprotein inhibitior	-	0.7701	77.01%
P-glycoprotein substrate	-	0.8728	87.28%
CYP3A4 substrate	+	0.5651	56.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7447	74.47%
CYP3A4 inhibition	-	0.9445	94.45%
CYP2C9 inhibition	-	0.9517	95.17%
CYP2C19 inhibition	-	0.9182	91.82%
CYP2D6 inhibition	-	0.9153	91.53%
CYP1A2 inhibition	-	0.9314	93.14%
CYP2C8 inhibition	+	0.5428	54.28%
CYP inhibitory promiscuity	-	0.8598	85.98%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6637	66.37%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8850	88.50%
Skin irritation	-	0.8035	80.35%
Skin corrosion	-	0.9654	96.54%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6836	68.36%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.9052	90.52%
skin sensitisation	-	0.9033	90.33%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6305	63.05%
Acute Oral Toxicity (c)	III	0.4873	48.73%
Estrogen receptor binding	+	0.6369	63.69%
Androgen receptor binding	+	0.5697	56.97%
Thyroid receptor binding	+	0.6463	64.63%
Glucocorticoid receptor binding	-	0.6089	60.89%
Aromatase binding	+	0.6670	66.70%
PPAR gamma	+	0.7423	74.23%
Honey bee toxicity	-	0.7722	77.22%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.6895	68.95%

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	99.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.13%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.49%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	89.44%	91.49%
CHEMBL2581	P07339	Cathepsin D	89.40%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.96%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.22%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.18%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.41%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.05%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.03%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.63%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.94%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.49%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.48%	95.83%
CHEMBL2243	O00519	Anandamide amidohydrolase	81.08%	97.53%
CHEMBL242	Q92731	Estrogen receptor beta	81.02%	98.35%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.46%	95.56%

Plants that contains it

• Stellera chamaejasme

Cross-Links

• PubChem: 75528886
• LOTUS: LTS0259708
• wikiData: Q104946414