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

Details

• Internal ID: 9f61fb3d-8c56-4a7a-8dec-4b72418da499
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-chromen-5-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(OC2=C1C(=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H](OC2=C1C(=CC(=C2)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)O
• InChI: InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-5-9(23)4-14-10(15)6-13(26)20(30-14)8-1-2-11(24)12(25)3-8/h1-5,13,16-29H,6-7H2/t13-,16-,17-,18+,19-,20-,21-/m1/s1
• InChI Key: ZESJTWVSXGZYTD-NJOLZHPTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₁₁
• Molecular Weight: 452.40 g/mol
• Exact Mass: 452.13186158 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -0.98
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• DTXSID701031661
• (?)-Epicatechin-5-O-beta-D-glucopyranoside
• (2S,3R,4S,5S,6R)-2-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-chroman-5-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5547	55.47%
Caco-2	-	0.9293	92.93%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.4774	47.74%
OATP2B1 inhibitior	-	0.5731	57.31%
OATP1B1 inhibitior	+	0.9256	92.56%
OATP1B3 inhibitior	+	0.9229	92.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6842	68.42%
P-glycoprotein inhibitior	-	0.7550	75.50%
P-glycoprotein substrate	-	0.8756	87.56%
CYP3A4 substrate	+	0.5681	56.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7608	76.08%
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	+	0.5654	56.54%
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	-	0.8904	89.04%
Skin irritation	-	0.8035	80.35%
Skin corrosion	-	0.9654	96.54%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6977	69.77%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	-	0.8927	89.27%
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	-	0.6478	64.78%
Acute Oral Toxicity (c)	III	0.4873	48.73%
Estrogen receptor binding	+	0.6772	67.72%
Androgen receptor binding	+	0.5576	55.76%
Thyroid receptor binding	+	0.6767	67.67%
Glucocorticoid receptor binding	-	0.5565	55.65%
Aromatase binding	+	0.5915	59.15%
PPAR gamma	+	0.7785	77.85%
Honey bee toxicity	-	0.7765	77.65%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5799	57.99%
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	99.68%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.91%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.38%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.38%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.63%	99.15%
CHEMBL2581	P07339	Cathepsin D	86.90%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.87%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.82%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.30%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.59%	99.17%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.57%	96.37%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.54%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.39%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.31%	90.00%
CHEMBL3194	P02766	Transthyretin	82.37%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.99%	95.83%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.95%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.23%	94.45%

Plants that contains it

• Apocynum venetum
• Elaeagnus angustifolia
• Ginkgo biloba
• Hippophae rhamnoides
• Machilus thunbergii
• Prunus tomentosa
• Reynoutria japonica
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum
• Senegalia catechu
• Tripterygium wilfordii
• Ziziphus jujuba

Cross-Links

• PubChem: 10343835
• NPASS: NPC192173
• LOTUS: LTS0081093
• wikiData: Q105373654