2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 9c541892-6fce-4a65-9f6a-a89dfc5ece81
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC(=C(C=C4)O)O)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=C(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)OC
• InChI: InChI=1S/C23H24O13/c1-32-12-6-11-14(16(28)21(12)33-2)17(29)22(20(34-11)8-3-4-9(25)10(26)5-8)36-23-19(31)18(30)15(27)13(7-24)35-23/h3-6,13,15,18-19,23-28,30-31H,7H2,1-2H3/t13-,15+,18+,19-,23+/m1/s1
• InChI Key: QJJFDGNJOXCQPD-LTGKLFRMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₃
• Molecular Weight: 508.40 g/mol
• Exact Mass: 508.12169082 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5074	50.74%
Caco-2	-	0.8484	84.84%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.5539	55.39%
OATP1B1 inhibitior	+	0.9357	93.57%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6629	66.29%
P-glycoprotein inhibitior	-	0.5306	53.06%
P-glycoprotein substrate	-	0.6391	63.91%
CYP3A4 substrate	+	0.6337	63.37%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.8862	88.62%
CYP2C9 inhibition	-	0.9258	92.58%
CYP2C19 inhibition	-	0.9329	93.29%
CYP2D6 inhibition	-	0.9457	94.57%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	+	0.8267	82.67%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8394	83.94%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.5236	52.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4524	45.24%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9356	93.56%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.7893	78.93%
Androgen receptor binding	+	0.6659	66.59%
Thyroid receptor binding	+	0.5153	51.53%
Glucocorticoid receptor binding	+	0.7582	75.82%
Aromatase binding	+	0.5605	56.05%
PPAR gamma	+	0.6674	66.74%
Honey bee toxicity	-	0.7521	75.21%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6549	65.49%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.61%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.45%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.42%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.18%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.02%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.94%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.98%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.72%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.63%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.98%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	87.47%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.13%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.68%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.10%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.68%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.51%	95.83%

Plants that contains it

• Ageratina calophylla
• Brickellia baccharidea
• Brickellia vernicosa
• Brickellia veronicaefolia
• Ipomopsis aggregata

Cross-Links

• PubChem: 162936705
• LOTUS: LTS0181403
• wikiData: Q105222701