Hexamethylquercetagetin

Details

• Internal ID: 032840d7-1f4b-4725-ab2b-8623e21291fb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-3,5,6,7-tetramethoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC)OC)OC)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC)OC)OC)OC)OC
• InChI: InChI=1S/C21H22O8/c1-23-12-8-7-11(9-13(12)24-2)18-21(28-6)17(22)16-14(29-18)10-15(25-3)19(26-4)20(16)27-5/h7-10H,1-6H3
• InChI Key: CHXSDKWBSFDZEU-UHFFFAOYSA-N
• Popularity: 70 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: 3.20
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 1251-84-9
• Quercetagetin hexamethyl ether
• 3,5,6,7,3',4'-Hexamethoxyflavone
• Oxyayanin B trimethyl ether
• Hexa-O-methylquercetagetin
• NSC-678108
• Flavone, 3,3',4',5,6,7-hexamethoxy-
• UNII-5MF6VX27BO
• 5MF6VX27BO
• 2-(3,4-dimethoxyphenyl)-3,5,6,7-tetramethoxychromen-4-one
• NSC678108
• Quercetagenin hexamethylether
• 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,6,7-tetramethoxy-
• 3,3',4',5,6,7-Hexamethoxyflavone
• 2-(3,4-Dimethoxyphenyl)-3,5,6,7-tetramethoxy-4H-chromen-4-one
• Quercitagetin hexamethyl ether
• SCHEMBL987569
• CHEMBL225698
• CHEBI:93682
• CHXSDKWBSFDZEU-UHFFFAOYSA-N
• DTXSID701301791
• HY-N4308
• 3,6,7,3',4'-Hexamethoxyflavone
• LMPK12113018
• AKOS037515016
• CCG-214271
• Flavone, 3,5,6,7,3',4'-hexamethoxy
• Flavone,3,3',4',5,6,7-hexamethoxy-
• NCI60_027979
• CS-0032712
• SR-05000002644
• SR-05000002644-1
• BRD-K95885906-001-01-8
• Q27165376
• 2-(3,4-dimethoxyphenyl)-3,5,6,7-tetramethoxy-chromen-4-one
• 2-(3,4-Dimethoxyphenyl)-3,5,6,7-tetramethoxy-4H-chromen-4-one #
• 2-(3,4-Dimethoxyphenyl)-3,5,6,7-tetramethoxy-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	+	0.8302	83.02%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9563	95.63%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6333	63.33%
P-glycoprotein inhibitior	+	0.9423	94.23%
P-glycoprotein substrate	-	0.7380	73.80%
CYP3A4 substrate	+	0.5174	51.74%
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	+	0.7976	79.76%
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	-	0.6869	68.69%
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	+	0.7759	77.59%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.5625	56.25%
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	-	0.7397	73.97%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.8931	89.31%
Androgen receptor binding	+	0.8107	81.07%
Thyroid receptor binding	+	0.6744	67.44%
Glucocorticoid receptor binding	+	0.7649	76.49%
Aromatase binding	+	0.5777	57.77%
PPAR gamma	+	0.7945	79.45%
Honey bee toxicity	-	0.8547	85.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
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	95.56%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.64%	86.33%
CHEMBL4302	P08183	P-glycoprotein 1	93.07%	92.98%
CHEMBL2581	P07339	Cathepsin D	89.17%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.93%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.65%	96.00%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	86.37%	85.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.25%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.16%	95.56%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.78%	94.03%
CHEMBL5903	Q04771	Activin receptor type-1	82.89%	89.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.88%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	82.71%	90.20%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.83%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.72%	96.09%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.07%	95.53%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.97%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.15%	97.14%

Plants that contains it

• Callicarpa pilosissima
• Chiliadenus montanus
• Citrus × aurantium
• Citrus japonica
• Dovyalis abyssinica
• Eucalyptus cordata
• Fagraea fragrans
• Nephelium ramboutan-ake
• Pallenis spinosa
• Pulicaria arabica
• Pulicaria sicula
• Vitex negundo

Cross-Links

• PubChem: 386331
• NPASS: NPC259058
• ChEMBL: CHEMBL225698
• LOTUS: LTS0109758
• wikiData: Q27165376