(2S)-7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

Details

• Internal ID: 98bbc7a4-5e28-4de7-8638-5cff9d9ce64f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=CC(=CC(=C2C1=O)O)OC3C(C(C(C(O3)CO)O)O)OC4C(C(CO4)(CO)O)O)C5=CC=C(C=C5)O
• SMILES (Isomeric): C1[C@H](OC2=CC(=CC(=C2C1=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O[C@H]4[C@@H]([C@](CO4)(CO)O)O)C5=CC=C(C=C5)O
• InChI: InChI=1S/C26H30O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-6,16,18,20-25,27-30,32-35H,7-10H2/t16-,18+,20+,21-,22+,23-,24+,25-,26+/m0/s1
• InChI Key: RZNUULHKDQNOPC-WJPYRASCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₁₄
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.55
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6445	64.45%
Caco-2	-	0.9146	91.46%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Mitochondria	0.6268	62.68%
OATP2B1 inhibitior	-	0.8478	84.78%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.9377	93.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6225	62.25%
P-glycoprotein inhibitior	-	0.6507	65.07%
P-glycoprotein substrate	-	0.6569	65.69%
CYP3A4 substrate	+	0.6771	67.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8457	84.57%
CYP3A4 inhibition	-	0.8434	84.34%
CYP2C9 inhibition	-	0.9185	91.85%
CYP2C19 inhibition	-	0.8482	84.82%
CYP2D6 inhibition	-	0.8986	89.86%
CYP1A2 inhibition	-	0.9073	90.73%
CYP2C8 inhibition	+	0.5678	56.78%
CYP inhibitory promiscuity	-	0.8029	80.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5523	55.23%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.8084	80.84%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.5154	51.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7125	71.25%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8757	87.57%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5915	59.15%
Acute Oral Toxicity (c)	III	0.5556	55.56%
Estrogen receptor binding	+	0.7968	79.68%
Androgen receptor binding	+	0.5766	57.66%
Thyroid receptor binding	+	0.5244	52.44%
Glucocorticoid receptor binding	-	0.5155	51.55%
Aromatase binding	+	0.7402	74.02%
PPAR gamma	+	0.7694	76.94%
Honey bee toxicity	-	0.6400	64.00%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5150	51.50%
Fish aquatic toxicity	+	0.7847	78.47%

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	99.70%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.24%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.92%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	96.39%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.83%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.11%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.99%	86.92%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.96%	94.00%
CHEMBL2581	P07339	Cathepsin D	91.37%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.01%	95.89%
CHEMBL4208	P20618	Proteasome component C5	89.81%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.16%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.30%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.10%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.79%	96.21%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.71%	91.07%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.13%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.97%	86.33%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.00%	85.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.95%	94.80%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.96%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.47%	94.73%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.33%	97.53%

Plants that contains it

• Apium graveolens
• Holarrhena pubescens

Cross-Links

• PubChem: 46882563
• LOTUS: LTS0116558
• wikiData: Q105248477