4',5-Dihydroxy-3',5',6,7-tetramethoxyflavone

Details

• Internal ID: d4c20e88-59c3-4177-941d-aa24ee1cf8b3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dimethoxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C(=C(C=C3O2)OC)OC)O
• InChI: InChI=1S/C19H18O8/c1-23-13-5-9(6-14(24-2)17(13)21)11-7-10(20)16-12(27-11)8-15(25-3)19(26-4)18(16)22/h5-8,21-22H,1-4H3
• InChI Key: XEHLDSAKZSXOFK-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 83133-17-9
• 5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dimethoxychromen-4-one
• 5,4'-Dihidroxy-6,7,3',5'-tetramethoxyflavone
• 5-Hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one
• MLS000863593
• MEGxp0_001427
• CHEMBL1524286
• ACon1_000425
• HMS2271N03
• LMPK12111272
• AKOS022184619
• NCGC00169092-01
• SMR000440715
• 4/',5-Dihydroxy-3/',5/',6,7-tetramethoxyflavone
• 5,4'-di-hydroxy 6,7,3',5'-tetramethoxy flavone
• BRD-K82024797-001-01-1
• 5-hydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-6,7-dimethoxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.7485	74.85%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.7154	71.54%
OATP1B1 inhibitior	+	0.9065	90.65%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5340	53.40%
P-glycoprotein inhibitior	+	0.7148	71.48%
P-glycoprotein substrate	-	0.7617	76.17%
CYP3A4 substrate	+	0.5132	51.32%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7237	72.37%
CYP2C9 inhibition	-	0.6863	68.63%
CYP2C19 inhibition	+	0.6566	65.66%
CYP2D6 inhibition	-	0.8329	83.29%
CYP1A2 inhibition	+	0.8642	86.42%
CYP2C8 inhibition	+	0.6247	62.47%
CYP inhibitory promiscuity	+	0.7231	72.31%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9825	98.25%
Eye irritation	+	0.5846	58.46%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.6864	68.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.8001	80.01%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8345	83.45%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.8725	87.25%
Androgen receptor binding	+	0.7255	72.55%
Thyroid receptor binding	+	0.6603	66.03%
Glucocorticoid receptor binding	+	0.7834	78.34%
Aromatase binding	+	0.6451	64.51%
PPAR gamma	+	0.7412	74.12%
Honey bee toxicity	-	0.8166	81.66%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.8969	89.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	35481.3 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	28183.8 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.02%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.70%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.53%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.75%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.61%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.86%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.57%	98.95%
CHEMBL3194	P02766	Transthyretin	82.96%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.94%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.00%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.71%	90.71%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.36%	94.42%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.12%	99.15%

Plants that contains it

• Artemisia mesatlantica
• Lantana montevidensis
• Mulguraea tridens
• Pachylobus normandii
• Riccia fluitans
• Scutellaria barbata

Cross-Links

• PubChem: 16681753
• NPASS: NPC276409
• ChEMBL: CHEMBL1524286
• LOTUS: LTS0059048
• wikiData: Q105326347