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

Details

• Internal ID: 9a825b86-444c-4481-8c43-6a535a8e3e42
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-3,6-dimethoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(2,3,4-trihydroxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=C(C(=C(C=C3)O)O)O)OC)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=C(C(=C(C=C3)O)O)O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C23H24O14/c1-33-21-10(36-23-19(32)18(31)15(28)11(6-24)37-23)5-9-12(16(21)29)17(30)22(34-2)20(35-9)7-3-4-8(25)14(27)13(7)26/h3-5,11,15,18-19,23-29,31-32H,6H2,1-2H3/t11-,15-,18+,19-,23-/m1/s1
• InChI Key: VRDVBYFMIGJXEG-VBUZMKOSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₄O₁₄
• Molecular Weight: 524.40 g/mol
• Exact Mass: 524.11660544 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.52
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• 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	-	0.8776	87.76%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6238	62.38%
OATP2B1 inhibitior	-	0.5568	55.68%
OATP1B1 inhibitior	+	0.8511	85.11%
OATP1B3 inhibitior	+	0.9678	96.78%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6358	63.58%
P-glycoprotein inhibitior	-	0.5972	59.72%
P-glycoprotein substrate	-	0.5466	54.66%
CYP3A4 substrate	+	0.6216	62.16%
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	+	0.6540	65.40%
CYP inhibitory promiscuity	-	0.7195	71.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7238	72.38%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.8305	83.05%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	+	0.6336	63.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4342	43.42%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9389	93.89%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8967	89.67%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.8410	84.10%
Androgen receptor binding	+	0.6273	62.73%
Thyroid receptor binding	+	0.5703	57.03%
Glucocorticoid receptor binding	+	0.7271	72.71%
Aromatase binding	+	0.5362	53.62%
PPAR gamma	+	0.6718	67.18%
Honey bee toxicity	-	0.8126	81.26%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
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	99.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.33%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.24%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.75%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.18%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.46%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.34%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.13%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.22%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.12%	95.56%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.39%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.20%	99.15%
CHEMBL220	P22303	Acetylcholinesterase	87.92%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	87.31%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.59%	85.14%
CHEMBL3194	P02766	Transthyretin	83.18%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.62%	96.00%
CHEMBL4208	P20618	Proteasome component C5	82.08%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.60%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.19%	95.83%

Plants that contains it

• Tridax procumbens

Cross-Links

• PubChem: 162863079
• LOTUS: LTS0182224
• wikiData: Q105291702