7-Methoxyflavone

Details

• Internal ID: 4d1d9e22-aa46-49ee-bedf-bfa22af9aba4
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 7-methoxy-2-phenylchromen-4-one
• SMILES (Canonical): COC1=CC2=C(C=C1)C(=O)C=C(O2)C3=CC=CC=C3
• SMILES (Isomeric): COC1=CC2=C(C=C1)C(=O)C=C(O2)C3=CC=CC=C3
• InChI: InChI=1S/C16H12O3/c1-18-12-7-8-13-14(17)10-15(19-16(13)9-12)11-5-3-2-4-6-11/h2-10H,1H3
• InChI Key: QKNDCRMJDZLFEG-UHFFFAOYSA-N
• Popularity: 64 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.26 g/mol
• Exact Mass: 252.078644241 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 22395-22-8
• 7-methoxy-2-phenyl-4H-chromen-4-one
• 7-methoxy-2-phenylchromen-4-one
• Flavone, 7-methoxy-
• 7-Methoxy-2-phenyl-chromen-4-one
• 7-Methoxy-2-phenylchromone
• UNII-XK561AP5UR
• XK561AP5UR
• 7-Methoxy-2-phenyl-4H-benzopyran-4-one
• NSC-741744
• 7-Methoxy Flavone
• Oprea1_076281
• BIDD:ER0421
• CHEMBL16782
• F3385-6145
• MEGxp0_001706
• SCHEMBL1373009
• ACon1_000207
• 7-METHOXYFLAVONE [VANDF]
• DTXSID80332790
• CHEBI:192603
• HY-N8487
• LMPK12110021
• MFCD00017462
• NSC741744
• STL100263
• AKOS001617181
• CCG-106707
• DS-4825
• MB00278
• NSC 741744
• NCGC00180781-01
• NCGC00180781-02
• PD143277
• CS-0144725
• EU-0071703
• FT-0638222
• FT-0698081
• M1423
• D70148
• AB00133543-03
• A878550
• SR-01000434441
• A1-00200
• J-014687
• SR-01000434441-1
• BRD-K00654887-001-01-5
• Q27293878
• InChI=1/C16H12O3/c1-18-12-7-8-13-14(17)10-15(19-16(13)9-12)11-5-3-2-4-6-11/h2-10H,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7381	73.81%
OATP2B1 inhibitior	-	0.8648	86.48%
OATP1B1 inhibitior	+	0.9622	96.22%
OATP1B3 inhibitior	+	0.9972	99.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6674	66.74%
P-glycoprotein inhibitior	+	0.7285	72.85%
P-glycoprotein substrate	-	0.9139	91.39%
CYP3A4 substrate	-	0.5299	52.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	+	0.5150	51.50%
CYP2C9 inhibition	+	0.9280	92.80%
CYP2C19 inhibition	+	0.9659	96.59%
CYP2D6 inhibition	-	0.9105	91.05%
CYP1A2 inhibition	+	0.9877	98.77%
CYP2C8 inhibition	+	0.4592	45.92%
CYP inhibitory promiscuity	+	0.7677	76.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9213	92.13%
Carcinogenicity (trinary)	Warning	0.4409	44.09%
Eye corrosion	-	0.7769	77.69%
Eye irritation	+	0.8628	86.28%
Skin irritation	-	0.5383	53.83%
Skin corrosion	-	0.9839	98.39%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.6435	64.35%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6146	61.46%
Acute Oral Toxicity (c)	III	0.8488	84.88%
Estrogen receptor binding	+	0.9216	92.16%
Androgen receptor binding	+	0.9653	96.53%
Thyroid receptor binding	+	0.6354	63.54%
Glucocorticoid receptor binding	+	0.9324	93.24%
Aromatase binding	+	0.9308	93.08%
PPAR gamma	+	0.7064	70.64%
Honey bee toxicity	-	0.8434	84.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7100	71.00%
Fish aquatic toxicity	+	0.7814	78.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL6164	O95271	Tankyrase-1	5000 nM	IC50	PMID: 24116873

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.19%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.19%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	94.63%	93.31%
CHEMBL2581	P07339	Cathepsin D	93.99%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.63%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.50%	86.33%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	89.85%	92.08%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	89.31%	92.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.84%	93.99%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.44%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.00%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.76%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.97%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.51%	89.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.97%	94.03%

Plants that contains it

• Anodendron affine
• Cedrela salvadorensis
• Conchocarpus heterophyllus
• Galium latoramosum
• Garcinia gummi-gutta
• Hertia cheirifolia
• Licaria chrysophylla
• Muntingia calabura
• Ormosia hosiei
• Ornithoglossum viride
• Petasites radiatus
• Pimelea simplex
• Schizanthus tricolor
• Sphaeranthus confertifolius

Cross-Links

• PubChem: 466268
• NPASS: NPC284424
• ChEMBL: CHEMBL16782
• LOTUS: LTS0105156
• wikiData: Q27293878