4'-Methoxyflavone

Details

• Internal ID: 3875bf72-846f-4055-8a7f-ef3529957652
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: 2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2
• InChI: InChI=1S/C16H12O3/c1-18-12-8-6-11(7-9-12)16-10-14(17)13-4-2-3-5-15(13)19-16/h2-10H,1H3
• InChI Key: OMICQBVLCVRFGN-UHFFFAOYSA-N
• Popularity: 87 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: 3.50
• Atomic LogP (AlogP): 3.47
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 4143-74-2
• 2-(4-methoxyphenyl)-4H-chromen-4-one
• 2-(4-methoxyphenyl)chromen-4-one
• 4H-1-Benzopyran-4-one, 2-(4-methoxyphenyl)-
• 4-Methoxy Flavone
• 2-(4-Methoxy-phenyl)-chromen-4-one
• CHEMBL16312
• 2-(4-Methoxyphenyl)-4-benzopyrone
• EINECS 223-968-8
• SR-01000471678
• 4' methoxyflavone
• 4''-methoxyflavone
• Flavone, 4'-methoxy
• Spectrum_000114
• Flavone, 4'-methoxy-
• Spectrum2_000774
• Spectrum3_001269
• Spectrum4_001629
• Spectrum5_000417
• CBMicro_029575
• ChemDiv2_004185
• Cambridge id 5324654
• CBiol_000291
• Oprea1_031095
• Oprea1_274709
• BSPBio_002838
• KBioGR_002037
• KBioSS_000554
• SPECTRUM240958
• cid_77793
• MLS000863607
• BIDD:ER0472
• SCHEMBL311931
• SPBio_000848
• F0400-0028
• MEGxp0_001873
• DTXSID0063319
• ACon1_002036
• KBio2_000554
• KBio2_003122
• KBio2_005690
• KBio3_002338
• 4l10
• CHEBI:114194
• HMS1380O05
• HMS2271I03
• 2-(4-methoxyphenyl)-chromen-4-one
• BDBM50310189
• CCG-40164
• ICCB2_000291
• MFCD00016934
• AKOS000603631
• SDCCGMLS-0066544.P001
• IDI1_002900
• NCGC00095556-01
• NCGC00095556-02
• NCGC00095556-03
• NCGC00178443-01
• NCGC00178443-02
• 2-(4-methoxy-phenyl)-4H-chromen-4-one
• 2-(4-methoxyphenyl)-1-benzopyran-4-one
• AS-56897
• PD002073
• SMR000440756
• BIM-0029447.P001
• EU-0042497
• FT-0733585
• M2887
• T72446
• AD-310/30361023
• SR-01000471678-1
• SR-01000471678-3
• BRD-K76337122-001-02-9
• BRD-K76337122-001-03-7
• Q27195318
• A63

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9152	91.52%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7381	73.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9339	93.39%
OATP1B3 inhibitior	+	0.9972	99.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5359	53.59%
P-glycoprotein inhibitior	-	0.4468	44.68%
P-glycoprotein substrate	-	0.9349	93.49%
CYP3A4 substrate	+	0.5678	56.78%
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	+	0.5000	50.00%
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	+	0.7435	74.35%
Skin irritation	-	0.5383	53.83%
Skin corrosion	-	0.9839	98.39%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3830	38.30%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6260	62.60%
Acute Oral Toxicity (c)	III	0.8488	84.88%
Estrogen receptor binding	+	0.9207	92.07%
Androgen receptor binding	+	0.9721	97.21%
Thyroid receptor binding	+	0.6747	67.47%
Glucocorticoid receptor binding	+	0.8445	84.45%
Aromatase binding	+	0.8459	84.59%
PPAR gamma	+	0.7308	73.08%
Honey bee toxicity	-	0.8510	85.10%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.7814	78.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	14125.4 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM	Potency	via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	44668.4 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	25118.9 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	1995.3 nM; 1995.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	1000 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	3981.1 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	2818.4 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2039	P27338	Monoamine oxidase B	27870 nM	IC50	PMID: 20045650
CHEMBL1293277	O15118	Niemann-Pick C1 protein	2511.9 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	11220.2 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	1995.3 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	10000 nM	Potency	via CMAUP
CHEMBL6164	O95271	Tankyrase-1	70.79 nM; 70.79 nM; 71 nM	IC50; IC50; IC50	PMID: 24116873; via Super-PRED; PMID: 24116873

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.44%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.59%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.00%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.85%	94.00%
CHEMBL1907	P15144	Aminopeptidase N	93.70%	93.31%
CHEMBL2581	P07339	Cathepsin D	93.30%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.02%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.76%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.63%	99.15%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.27%	93.99%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.99%	92.67%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	85.76%	87.67%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.69%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.07%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	82.62%	94.73%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	82.57%	89.23%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.55%	93.65%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.34%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.61%	97.14%

Plants that contains it

• Ammopiptanthus mongolicus
• Cullen corylifolium

Cross-Links

• PubChem: 77793
• NPASS: NPC2771
• ChEMBL: CHEMBL16312
• LOTUS: LTS0257243
• wikiData: Q27195318