5,7-Dihydroxy-8,3',4',5'-tetramethoxyflavone

Details

• Internal ID: 427ed2e4-0c6b-46e9-be70-810501184caa
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5,7-dihydroxy-8-methoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)OC
• InChI: InChI=1S/C19H18O8/c1-23-14-5-9(6-15(24-2)18(14)26-4)13-8-11(21)16-10(20)7-12(22)17(25-3)19(16)27-13/h5-8,20,22H,1-4H3
• InChI Key: ZMFBCRNURMVYEI-UHFFFAOYSA-N
• Popularity: 2 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

• RefChem:101373
• 5,7-dihydroxy-8-methoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• 32348-78-0
• 3',4',5'-Trimethoxywogonin
• LMPK12111415

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9417	94.17%
Caco-2	+	0.8169	81.69%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	0.7149	71.49%
OATP1B1 inhibitior	+	0.9348	93.48%
OATP1B3 inhibitior	+	0.8767	87.67%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5870	58.70%
P-glycoprotein inhibitior	+	0.7588	75.88%
P-glycoprotein substrate	-	0.8578	85.78%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.6154	61.54%
CYP2C9 inhibition	-	0.7484	74.84%
CYP2C19 inhibition	+	0.5640	56.40%
CYP2D6 inhibition	-	0.7310	73.10%
CYP1A2 inhibition	+	0.8610	86.10%
CYP2C8 inhibition	+	0.5100	51.00%
CYP inhibitory promiscuity	+	0.8068	80.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6142	61.42%
Eye corrosion	-	0.9818	98.18%
Eye irritation	+	0.6431	64.31%
Skin irritation	-	0.7187	71.87%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	-	0.7064	70.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6088	60.88%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9352	93.52%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6709	67.09%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	+	0.9528	95.28%
Androgen receptor binding	+	0.7018	70.18%
Thyroid receptor binding	+	0.7175	71.75%
Glucocorticoid receptor binding	+	0.8509	85.09%
Aromatase binding	+	0.7973	79.73%
PPAR gamma	+	0.7355	73.55%
Honey bee toxicity	-	0.7670	76.70%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.8724	87.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.71%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.32%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.06%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.71%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.21%	95.56%
CHEMBL3194	P02766	Transthyretin	87.59%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.58%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.87%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.48%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.97%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	80.92%	94.73%

Plants that contains it

• Xerochrysum viscosum

Cross-Links

• PubChem: 44258625
• LOTUS: LTS0242485
• wikiData: Q105379415