5,8-Dihydroxy-3,6,7-trimethoxyflavone

Details

• Internal ID: a61bca4a-8a76-4c04-a93b-59be0510843f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5,8-dihydroxy-3,6,7-trimethoxy-2-phenylchromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1O)C(=O)C(=C(O2)C3=CC=CC=C3)OC)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1O)C(=O)C(=C(O2)C3=CC=CC=C3)OC)O)OC
• InChI: InChI=1S/C18H16O7/c1-22-16-11(19)10-12(20)17(23-2)18(24-3)13(21)15(10)25-14(16)9-7-5-4-6-8-9/h4-8,20-21H,1-3H3
• InChI Key: UJPCZWVHMQYZNR-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₇
• Molecular Weight: 344.30 g/mol
• Exact Mass: 344.08960285 g/mol
• Topological Polar Surface Area (TPSA): 94.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• LMPK12113293

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	-	0.5793	57.93%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.7195	71.95%
OATP1B1 inhibitior	+	0.9363	93.63%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6230	62.30%
P-glycoprotein inhibitior	+	0.8619	86.19%
P-glycoprotein substrate	-	0.9313	93.13%
CYP3A4 substrate	-	0.5620	56.20%
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	+	0.5208	52.08%
CYP inhibitory promiscuity	+	0.7231	72.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9825	98.25%
Eye irritation	+	0.6878	68.78%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.5337	53.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5195	51.95%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.7053	70.53%
Androgen receptor binding	+	0.6112	61.12%
Thyroid receptor binding	+	0.5882	58.82%
Glucocorticoid receptor binding	+	0.7927	79.27%
Aromatase binding	+	0.6031	60.31%
PPAR gamma	+	0.7891	78.91%
Honey bee toxicity	-	0.9138	91.38%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.92%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.47%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.67%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.29%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.93%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.89%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.73%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.03%	89.00%
CHEMBL3959	P16083	Quinone reductase 2	83.87%	89.49%

Plants that contains it

• Pseudognaphalium gaudichaudianum

Cross-Links

• PubChem: 15290567
• LOTUS: LTS0155447
• wikiData: Q105274081