5,6,2',3',4'-Pentamethoxyflavone

Details

• Internal ID: db36e282-d4d7-40f6-8528-f7bee1b13321
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 6-O-methylated flavonoids
• IUPAC Name: 5,6-dimethoxy-2-(2,3,4-trimethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C(=C(C=C1)C2=CC(=O)C3=C(O2)C=CC(=C3OC)OC)OC)OC
• SMILES (Isomeric): COC1=C(C(=C(C=C1)C2=CC(=O)C3=C(O2)C=CC(=C3OC)OC)OC)OC
• InChI: InChI=1S/C20H20O7/c1-22-14-9-8-13-17(19(14)25-4)12(21)10-16(27-13)11-6-7-15(23-2)20(26-5)18(11)24-3/h6-10H,1-5H3
• InChI Key: RXRZZDZJENMNEF-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.40 g/mol
• Exact Mass: 372.12090297 g/mol
• Topological Polar Surface Area (TPSA): 72.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 5,6,2',3',4'-Pentamethoxyflavone
• SCHEMBL16894663
• DTXSID80555144
• LMPK12110115
• 5,6-Dimethoxy-2-(2,3,4-trimethoxyphenyl)-4H-chromen-4-one
• 5,6-Dimethoxy-2-(2,3,4-trimethoxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.8878	88.78%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9390	93.90%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6094	60.94%
P-glycoprotein inhibitior	+	0.9599	95.99%
P-glycoprotein substrate	-	0.5864	58.64%
CYP3A4 substrate	-	0.5186	51.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	+	0.6138	61.38%
CYP2C9 inhibition	-	0.7985	79.85%
CYP2C19 inhibition	+	0.7445	74.45%
CYP2D6 inhibition	-	0.9546	95.46%
CYP1A2 inhibition	+	0.9694	96.94%
CYP2C8 inhibition	-	0.5789	57.89%
CYP inhibitory promiscuity	+	0.8123	81.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5636	56.36%
Eye corrosion	-	0.9682	96.82%
Eye irritation	-	0.6887	68.87%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	-	0.5664	56.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7283	72.83%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9439	94.39%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.5884	58.84%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.9336	93.36%
Androgen receptor binding	+	0.8706	87.06%
Thyroid receptor binding	+	0.6953	69.53%
Glucocorticoid receptor binding	+	0.8544	85.44%
Aromatase binding	+	0.6669	66.69%
PPAR gamma	+	0.7379	73.79%
Honey bee toxicity	-	0.8415	84.15%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9192	91.92%

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	93.85%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.11%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.92%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.98%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.95%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.55%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	85.00%	90.20%
CHEMBL2535	P11166	Glucose transporter	84.57%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.57%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	82.17%	91.49%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.27%	96.67%

Plants that contains it

• Casimiroa tetrameria
• Kopsia profunda
• Tropaeolum majus

Cross-Links

• PubChem: 14055877
• NPASS: NPC174438
• LOTUS: LTS0120257
• wikiData: Q82436399