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

Details

• Internal ID: 3a33da76-0c2f-4d93-9534-1f805070d5a2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 6-O-methylated flavonoids
• IUPAC Name: 5,6-dimethoxy-2-(2,3,4,6-tetramethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C=C1)OC(=CC2=O)C3=C(C(=C(C=C3OC)OC)OC)OC)OC
• SMILES (Isomeric): COC1=C(C2=C(C=C1)OC(=CC2=O)C3=C(C(=C(C=C3OC)OC)OC)OC)OC
• InChI: InChI=1S/C21H22O8/c1-23-13-8-7-12-17(19(13)26-4)11(22)9-15(29-12)18-14(24-2)10-16(25-3)20(27-5)21(18)28-6/h7-10H,1-6H3
• InChI Key: WRSCDVAVPNHFPB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₈
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.13146766 g/mol
• Topological Polar Surface Area (TPSA): 81.70 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 100742-33-4
• 4H-1-Benzopyran-4-one, 5,6-dimethoxy-2-(2,3,4,6-tetramethoxyphenyl)-
• 5,6-dimethoxy-2-(2,3,4,6-tetramethoxyphenyl)chromen-4-one
• DTXSID40143480
• LMPK12110114

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.8972	89.72%
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	+	0.9290	92.90%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7049	70.49%
P-glycoprotein inhibitior	+	0.9311	93.11%
P-glycoprotein substrate	-	0.7612	76.12%
CYP3A4 substrate	-	0.5109	51.09%
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	+	0.6109	61.09%
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	-	0.6447	64.47%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	+	0.5036	50.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6882	68.82%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9439	94.39%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6606	66.06%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.8913	89.13%
Androgen receptor binding	+	0.7410	74.10%
Thyroid receptor binding	+	0.6953	69.53%
Glucocorticoid receptor binding	+	0.8070	80.70%
Aromatase binding	+	0.6338	63.38%
PPAR gamma	+	0.7418	74.18%
Honey bee toxicity	-	0.8586	85.86%
Biodegradation	-	0.8500	85.00%
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	94.03%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.45%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.08%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.30%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.25%	98.95%
CHEMBL2535	P11166	Glucose transporter	86.99%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.04%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.07%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	83.67%	90.20%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.81%	94.03%
CHEMBL3401	O75469	Pregnane X receptor	80.40%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.07%	90.00%

Plants that contains it

• Casimiroa greggii

Cross-Links

• PubChem: 180914
• LOTUS: LTS0121210
• wikiData: Q83007362