8-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

Details

• Internal ID: 8a3d46a5-4d63-45eb-96cc-f3652507703d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 8-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(C(OC2C3=C(C=C(C4=C3OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H]([C@@H]([C@H](O1)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2C3=C(C=C(C4=C3OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C26H28O15/c27-6-16-20(35)21(36)25(41-26-22(37)19(34)14(33)7-38-26)24(40-16)18-12(31)4-11(30)17-13(32)5-15(39-23(17)18)8-1-2-9(28)10(29)3-8/h1-5,14,16,19-22,24-31,33-37H,6-7H2/t14-,16+,19-,20+,21-,22+,24-,25+,26-/m1/s1
• InChI Key: RQLWDYSEFWBFBP-VXSQXEALSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₅
• Molecular Weight: 580.50 g/mol
• Exact Mass: 580.14282018 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.74
• H-Bond Acceptor: 15
• H-Bond Donor: 10
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5110	51.10%
Caco-2	-	0.9294	92.94%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5571	55.71%
OATP1B1 inhibitior	+	0.8904	89.04%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8013	80.13%
P-glycoprotein inhibitior	-	0.5930	59.30%
P-glycoprotein substrate	-	0.6328	63.28%
CYP3A4 substrate	+	0.6450	64.50%
CYP2C9 substrate	-	0.6621	66.21%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9644	96.44%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.9304	93.04%
CYP2C8 inhibition	+	0.6147	61.47%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.9028	90.28%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.6272	62.72%
Human Ether-a-go-go-Related Gene inhibition	-	0.4108	41.08%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7538	75.38%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8951	89.51%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.8345	83.45%
Androgen receptor binding	+	0.7314	73.14%
Thyroid receptor binding	+	0.5584	55.84%
Glucocorticoid receptor binding	+	0.5528	55.28%
Aromatase binding	+	0.6679	66.79%
PPAR gamma	+	0.7522	75.22%
Honey bee toxicity	-	0.6833	68.33%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7253	72.53%

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	99.79%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.93%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.79%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.32%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.65%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.30%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.44%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.71%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.64%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.18%	86.33%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.94%	95.83%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.65%	91.24%
CHEMBL308	P06493	Cyclin-dependent kinase 1	85.92%	91.73%
CHEMBL3401	O75469	Pregnane X receptor	85.45%	94.73%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.36%	80.33%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	84.04%	89.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.78%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.25%	95.89%

Plants that contains it

• Adonis vernalis

Cross-Links

• PubChem: 162974569
• LOTUS: LTS0015470
• wikiData: Q105243413