Quercetin pentamethyl ether

Details

• Internal ID: b76d1496-42e3-4a4b-9e80-0153bfa0db0e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(O2)C=C(C=C3OC)OC)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(O2)C=C(C=C3OC)OC)OC)OC
• InChI: InChI=1S/C20H20O7/c1-22-12-9-15(25-4)17-16(10-12)27-19(20(26-5)18(17)21)11-6-7-13(23-2)14(8-11)24-3/h6-10H,1-5H3
• InChI Key: ALGDHWVALRSLBT-UHFFFAOYSA-N
• Popularity: 78 references 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: 3.20
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 1247-97-8
• Pentamethylquercetin
• Pentamethoxyquercetin
• Penta-O-methylquercitin
• Quercetin-3,5,7,3',4'-pentamethyl ether
• 3,5,7,3',4'-pentamethoxyflavone
• 2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxychromen-4-one
• NSC-115922
• 3,3',4',5,7-Pentamethoxyflavone
• 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-
• CHEMBL19032
• 2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-4H-chromen-4-one
• QUERCETIN-3,5,7,3,4-PENTAMETHYLETHER
• V6J41K636O
• 3,5,7,3',4'-Pentamethyl ether
• NSC 115922
• NSC-618936
• Flavone, 3,3',4',5,7-pentamethoxy-
• Quercetin 3,5,7,3,4-pentamethyl ether
• 3,5,7,3 inverted exclamation marka,4 inverted exclamation marka-Pentamethoxyflavone
• Spectrum_001718
• Quercetin-3,5,7,3',4'-pentamethylether
• Quercetin 3,5,7,3',4'-pentamethyl ether
• Spectrum2_001804
• Spectrum3_001719
• Spectrum4_001790
• Spectrum5_000439
• BSPBio_003338
• KBioGR_002341
• KBioSS_002198
• MLS001048983
• SPECTRUM1600075
• UNII-V6J41K636O
• SPBio_001787
• SCHEMBL2286327
• 3,4',5,7-Pentamethoxyflavone
• KBio2_002198
• KBio2_004766
• KBio2_007334
• KBio3_002558
• DTXSID10154467
• ALGDHWVALRSLBT-UHFFFAOYSA-N
• HMS2268P21
• HY-N7690
• TUM-8437
• 2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-4h-1-benzopyran-4-one
• 3,3`,4`,5,7-Pentamethoxyflavone
• 4H-1-Benzopyran-4-one,2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-
• BDBM50404748
• CCG-38450
• Flavone,3',4',5,7-pentamethoxy-
• LMPK12112772
• MFCD01004607
• NSC115922
• NSC618936
• STL512455
• AKOS030487720
• SDCCGMLS-0066841.P001
• NCGC00095759-01
• NCGC00095759-02
• NCGC00178132-01
• MS-26004
• SMR000386999
• CS-0135217
• FT-0716793
• E80655
• AB00637125-07
• Quercetin 3, 5, 7, 3', 4'-pentamethylether
• SR-01000758970
• SR-01000758970-2
• 2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-chromen-4-one
• 4H-1-Benzopyran-4-one,4-dimethoxyphenyl)-3,5,7-trimethoxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.8774	87.74%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9632	96.32%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7791	77.91%
P-glycoprotein inhibitior	+	0.9484	94.84%
P-glycoprotein substrate	-	0.8547	85.47%
CYP3A4 substrate	+	0.5220	52.20%
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	+	0.7408	74.08%
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	+	0.6223	62.23%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7448	74.48%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	+	0.6085	60.85%
skin sensitisation	-	0.9439	94.39%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6981	69.81%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.8941	89.41%
Androgen receptor binding	+	0.8064	80.64%
Thyroid receptor binding	+	0.6255	62.55%
Glucocorticoid receptor binding	+	0.8051	80.51%
Aromatase binding	+	0.6099	60.99%
PPAR gamma	+	0.7997	79.97%
Honey bee toxicity	-	0.8747	87.47%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9192	91.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	19952.6 nM	Potency	via CMAUP
CHEMBL5393	Q9UNQ0	ATP-binding cassette sub-family G member 2	1880 nM; 822 nM; 822 nM	IC50; IC50; IC50	PMID: 23851114; PMID: 23851114; via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	1258.9 nM; 1258.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM; 1000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	26350 nM	IC50	PMID: 23851114
CHEMBL4302	P08183	P-glycoprotein 1	23400 nM	IC50	PMID: 23851114
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	10000 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.35%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.04%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.06%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.83%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.96%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.34%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.96%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.45%	94.45%
CHEMBL1907	P15144	Aminopeptidase N	85.24%	93.31%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.15%	91.11%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	83.42%	94.03%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	82.26%	85.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.96%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.85%	95.78%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.29%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	80.35%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.23%	97.14%

Plants that contains it

• Acalypha australis
• Aconitum variegatum
• Aglaia odorata
• Amorphophallus konjac
• Andromeda polifolia
• Aniba santalodora
• Astragalus circassicus
• Beilschmiedia madang
• Bethencourtia palmensis
• Boesenbergia rotunda
• Boswellia ovalifoliolata
• Campanula bayerniana
• Caucasalia pontica
• Centaurea scoparia
• Centaurea sphaerocephala subsp. sphaerocephala
• Colchicum filifolium
• Dacrycarpus dacrydioides
• Dialium excelsum
• Drymaria cordata
• Erythrina subumbrans
• Euphorbia hylonoma
• Genista lydia
• Hardenbergia violacea
• Heliotropium marifolium
• Helleborus niger subsp. macranthus
• Hemionitis pilifera
• Hemionitis pteridioides
• Kaempferia parviflora
• Lepechinia urbanii
• Lindelofia anchusoides subsp. macrostyla
• Lonchocarpus chiricanus
• Maclura cochinchinensis
• Melicope subunifoliolata
• Melicope triphylla
• Mentzelia decapetala
• Mimosa pigra
• Mucuna holtonii
• Oncosiphon sabulosus
• Ostrya carpinifolia
• Pteris bella
• Pterocaulon serrulatum
• Pulsatilla chinensis
• Quercus marilandica
• Rubia argyi
• Salix rosmarinifolia
• Salvia lavanduloides
• Salvia patens
• Salvia virgata
• Scapania bolanderi
• Stephania dielsiana
• Trichilia heudelotii
• Trichosanthes scabra
• Vangueria agrestis
• Vincetoxicum forrestii

Cross-Links

• PubChem: 97332
• NPASS: NPC310259
• ChEMBL: CHEMBL19032
• LOTUS: LTS0234816
• wikiData: Q83021718