[(2R,3R,4S,5R,6S)-6-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 62fd5b41-c586-4a6f-8255-e07768d758aa
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3R,4S,5R,6S)-6-[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O
• InChI: InChI=1S/C23H22O14/c1-7(24)34-6-14-17(30)19(32)20(33)23(36-14)37-22-18(31)15-10(26)4-9(25)5-13(15)35-21(22)8-2-11(27)16(29)12(28)3-8/h2-5,14,17,19-20,23,25-30,32-33H,6H2,1H3/t14-,17+,19+,20-,23+/m1/s1
• InChI Key: SVRJGKAZQHHOSZ-UOCKATJYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₄
• Molecular Weight: 522.40 g/mol
• Exact Mass: 522.10095537 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.26
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5759	57.59%
Caco-2	-	0.9090	90.90%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6926	69.26%
OATP2B1 inhibitior	-	0.5493	54.93%
OATP1B1 inhibitior	+	0.8335	83.35%
OATP1B3 inhibitior	+	0.9515	95.15%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.6614	66.14%
P-glycoprotein inhibitior	-	0.4558	45.58%
P-glycoprotein substrate	-	0.6585	65.85%
CYP3A4 substrate	+	0.6367	63.67%
CYP2C9 substrate	+	0.5334	53.34%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.9505	95.05%
CYP2C9 inhibition	-	0.9129	91.29%
CYP2C19 inhibition	-	0.9233	92.33%
CYP2D6 inhibition	-	0.9603	96.03%
CYP1A2 inhibition	-	0.8935	89.35%
CYP2C8 inhibition	+	0.8003	80.03%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7134	71.34%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8795	87.95%
Skin irritation	-	0.8133	81.33%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6557	65.57%
Micronuclear	+	0.5892	58.92%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9339	93.39%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8439	84.39%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.8272	82.72%
Androgen receptor binding	+	0.7077	70.77%
Thyroid receptor binding	-	0.5580	55.80%
Glucocorticoid receptor binding	+	0.6459	64.59%
Aromatase binding	-	0.5285	52.85%
PPAR gamma	+	0.6038	60.38%
Honey bee toxicity	-	0.8402	84.02%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9613	96.13%

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	99.63%	91.11%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	98.02%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.56%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.84%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.53%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.70%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.57%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.51%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.08%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.02%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	89.87%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.46%	94.45%
CHEMBL3194	P02766	Transthyretin	83.98%	90.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.47%	94.42%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.24%	99.15%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	82.04%	80.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.96%	94.80%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.36%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.33%	94.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.27%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.07%	95.50%

Plants that contains it

• Austrocedrus chilensis
• Nymphaea odorata

Cross-Links

• PubChem: 101068307
• NPASS: NPC252201
• LOTUS: LTS0028819
• wikiData: Q105262393