3',4',5',5,7-Pentamethoxyflavone

Details

• Internal ID: 6318e9df-b9bb-4a9c-ae72-1d95cb75c835
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC)C(=O)C=C(O2)C3=CC(=C(C(=C3)OC)OC)OC
• SMILES (Isomeric): COC1=CC2=C(C(=C1)OC)C(=O)C=C(O2)C3=CC(=C(C(=C3)OC)OC)OC
• InChI: InChI=1S/C20H20O7/c1-22-12-8-15(23-2)19-13(21)10-14(27-16(19)9-12)11-6-17(24-3)20(26-5)18(7-11)25-4/h6-10H,1-5H3
• InChI Key: GIKVSFNAEBQLGB-UHFFFAOYSA-N
• Popularity: 18 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: 3.00
• Atomic LogP (AlogP): 3.50
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 3',4',5',5,7-Pentamethoxyflavone
• 5,7,3',4',5'-Pentamethoxyflavone
• 5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• 5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one
• 3',?4',?5',?5,?7-?Pentamethoxyflavone
• CHEMBL2074901
• Tricetin 5,7,3',4',5'-pentamethyl ether
• 4H-1-Benzopyran-4-one, 5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-
• Tricetin Pentamethyl Ether
• 3',4',5,5',7-Pentamethoxyflavone
• SCHEMBL1422009
• DTXSID50333239
• 3-4-5-5-7-Pentamethoxyflavone
• GIKVSFNAEBQLGB-UHFFFAOYSA-N
• HY-N7029
• 3',4',5',5,7-entamethoxyflavone
• BDBM50420207
• LMPK12111076
• MFCD00017634
• 3,4,5,5,7-PENTAMETHOXYFLAVONE
• MS-26005
• PD167275
• 5,7,3/',4/',5/'-Pentamethoxyflavone
• CS-0101599
• FT-0614117
• E88585
• 5,7,3 inverted exclamation mark ,4 inverted exclamation mark ,5 inverted exclamation mark -Pentamethoxy flavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9901	99.01%
Caco-2	+	0.8996	89.96%
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	+	0.9563	95.63%
OATP1B3 inhibitior	+	0.9919	99.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6454	64.54%
P-glycoprotein inhibitior	+	0.9511	95.11%
P-glycoprotein substrate	-	0.9051	90.51%
CYP3A4 substrate	-	0.5088	50.88%
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	+	0.4616	46.16%
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	+	0.5581	55.81%
Skin irritation	-	0.7565	75.65%
Skin corrosion	-	0.9845	98.45%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6802	68.02%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9439	94.39%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6050	60.50%
Acute Oral Toxicity (c)	II	0.6245	62.45%
Estrogen receptor binding	+	0.9302	93.02%
Androgen receptor binding	+	0.7001	70.01%
Thyroid receptor binding	+	0.6812	68.12%
Glucocorticoid receptor binding	+	0.8049	80.49%
Aromatase binding	+	0.6699	66.99%
PPAR gamma	+	0.7650	76.50%
Honey bee toxicity	-	0.7628	76.28%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9192	91.92%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4302	P08183	P-glycoprotein 1	400 nM	IC50	PMID: 15240100

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.65%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.45%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.86%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.09%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.96%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.41%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	85.10%	93.31%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.42%	93.99%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.87%	96.77%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.67%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.30%	95.50%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.09%	94.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.12%	96.00%

Plants that contains it

• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Ficus formosana
• Ficus maxima
• Gardenia fosbergii
• Gardenia jasminoides
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Murraya exotica
• Murraya paniculata
• Murraya paniculata
• Neoraputia alba
• Odixia angusta
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Taxodium huegelii
• Vitex madiensis

Cross-Links

• PubChem: 493376
• NPASS: NPC29536
• ChEMBL: CHEMBL2074901
• LOTUS: LTS0199030
• wikiData: Q72499891