5,5'-Dihydroxy-8,2',4'-trimethoxyflavone

Details

• Internal ID: aa4f9ee6-06d1-4679-bcdd-c10c7e51a729
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-(5-hydroxy-2,4-dimethoxyphenyl)-8-methoxychromen-4-one
• SMILES (Canonical): COC1=C2C(=C(C=C1)O)C(=O)C=C(O2)C3=CC(=C(C=C3OC)OC)O
• SMILES (Isomeric): COC1=C2C(=C(C=C1)O)C(=O)C=C(O2)C3=CC(=C(C=C3OC)OC)O
• InChI: InChI=1S/C18H16O7/c1-22-13-5-4-10(19)17-12(21)7-15(25-18(13)17)9-6-11(20)16(24-3)8-14(9)23-2/h4-8,19-20H,1-3H3
• InChI Key: PXDGVALZEAFXRJ-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: 2.90
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.8994	89.94%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.5723	57.23%
OATP1B1 inhibitior	+	0.8821	88.21%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6511	65.11%
P-glycoprotein inhibitior	+	0.7008	70.08%
P-glycoprotein substrate	-	0.8112	81.12%
CYP3A4 substrate	+	0.5104	51.04%
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	+	0.5327	53.27%
CYP inhibitory promiscuity	+	0.7231	72.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9825	98.25%
Eye irritation	+	0.8172	81.72%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	+	0.6136	61.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.5701	57.01%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5186	51.86%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.9179	91.79%
Androgen receptor binding	+	0.8492	84.92%
Thyroid receptor binding	+	0.7590	75.90%
Glucocorticoid receptor binding	+	0.8600	86.00%
Aromatase binding	+	0.6901	69.01%
PPAR gamma	+	0.8135	81.35%
Honey bee toxicity	-	0.8561	85.61%
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
CHEMBL1951	P21397	Monoamine oxidase A	95.50%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.79%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.67%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.32%	95.56%
CHEMBL3194	P02766	Transthyretin	92.57%	90.71%
CHEMBL2581	P07339	Cathepsin D	90.24%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.06%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.78%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.11%	99.15%
CHEMBL1255126	O15151	Protein Mdm4	84.85%	90.20%
CHEMBL2535	P11166	Glucose transporter	83.56%	98.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.20%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.03%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	81.05%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.83%	90.71%

Plants that contains it

• Artemisia giraldii

Cross-Links

• PubChem: 10382865
• LOTUS: LTS0259919
• wikiData: Q105216113