5,4'-Dihydroxy-6,7,8,3',5'-pentamethoxyflavone

Details

• Internal ID: de616d2f-5fc9-49bf-b357-4ccf62e0e2a6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-6,7,8-trimethoxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O
• InChI: InChI=1S/C20H20O9/c1-24-12-6-9(7-13(25-2)15(12)22)11-8-10(21)14-16(23)18(26-3)20(28-5)19(27-4)17(14)29-11/h6-8,22-23H,1-5H3
• InChI Key: GSQDOAHDMWDTMG-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₉
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.11073221 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• LMPK12111498
• 5,4'-dihydroxy 6,7,8,3',5'-penta methoxy flavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.6401	64.01%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.7176	71.76%
OATP1B1 inhibitior	+	0.8998	89.98%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6031	60.31%
P-glycoprotein inhibitior	+	0.7422	74.22%
P-glycoprotein substrate	-	0.8213	82.13%
CYP3A4 substrate	-	0.5088	50.88%
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	+	0.5547	55.47%
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	+	0.5522	55.22%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.5864	58.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.8287	82.87%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7262	72.62%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.8619	86.19%
Androgen receptor binding	+	0.7321	73.21%
Thyroid receptor binding	+	0.6999	69.99%
Glucocorticoid receptor binding	+	0.7552	75.52%
Aromatase binding	+	0.6042	60.42%
PPAR gamma	+	0.6877	68.77%
Honey bee toxicity	-	0.8294	82.94%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6449	64.49%
Fish aquatic toxicity	+	0.8969	89.69%

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	97.44%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.51%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.21%	89.00%
CHEMBL2581	P07339	Cathepsin D	89.76%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.53%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.17%	95.56%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	89.16%	98.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.22%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.17%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.56%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.41%	99.15%
CHEMBL3194	P02766	Transthyretin	81.38%	90.71%

Plants that contains it

• Cleome droserifolia

Cross-Links

• PubChem: 10386481
• LOTUS: LTS0257610
• wikiData: Q105017556