5,7-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

Details

• Internal ID: 35d49a36-2ae2-4c5e-ba4d-453467f0a931
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(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): C[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/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3/t6-,14-,17+,18+,21+/m0/s1
• InChI Key: DCYOADKBABEMIQ-YIFFCZEQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09547607 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.19
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8357	83.57%
Caco-2	-	0.8068	80.68%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	+	0.5893	58.93%
OATP1B1 inhibitior	+	0.8799	87.99%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7099	70.99%
P-glycoprotein inhibitior	-	0.5484	54.84%
P-glycoprotein substrate	-	0.6164	61.64%
CYP3A4 substrate	+	0.6028	60.28%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.5306	53.06%
CYP2C8 inhibition	+	0.8057	80.57%
CYP inhibitory promiscuity	-	0.5648	56.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7532	75.32%
Skin irritation	-	0.6220	62.20%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5867	58.67%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5447	54.47%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8303	83.03%
Acute Oral Toxicity (c)	III	0.5184	51.84%
Estrogen receptor binding	+	0.7235	72.35%
Androgen receptor binding	+	0.6849	68.49%
Thyroid receptor binding	+	0.5520	55.20%
Glucocorticoid receptor binding	+	0.7165	71.65%
Aromatase binding	-	0.5301	53.01%
PPAR gamma	+	0.6887	68.87%
Honey bee toxicity	-	0.8422	84.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.9457	94.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	707.9 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	891.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.56%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.01%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.93%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	96.28%	95.64%
CHEMBL2581	P07339	Cathepsin D	95.10%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.78%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	93.15%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.79%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.01%	97.36%
CHEMBL3194	P02766	Transthyretin	89.65%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.34%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.42%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.81%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.84%	99.15%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.66%	94.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.84%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.74%	96.09%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.66%	91.38%
CHEMBL4208	P20618	Proteasome component C5	81.05%	90.00%

Plants that contains it

• Acer truncatum
• Ardisia japonica
• Bridelia ferruginea
• Cyclamen purpurascens
• Hypericum scabrum
• Moquilea pyrifolia
• Myrtus communis
• Phyllanthus emblica
• Plumbago europaea
• Sedum crassularia

Cross-Links

• PubChem: 16103933
• NPASS: NPC32226
• LOTUS: LTS0199262
• wikiData: Q104976144