5-Methoxyflavone

Details

• Internal ID: 1795f713-a68c-48aa-8595-5d3a4685e182
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 5-O-methylated flavonoids
• IUPAC Name: 5-methoxy-2-phenylchromen-4-one
• SMILES (Canonical): COC1=CC=CC2=C1C(=O)C=C(O2)C3=CC=CC=C3
• SMILES (Isomeric): COC1=CC=CC2=C1C(=O)C=C(O2)C3=CC=CC=C3
• InChI: InChI=1S/C16H12O3/c1-18-13-8-5-9-14-16(13)12(17)10-15(19-14)11-6-3-2-4-7-11/h2-10H,1H3
• InChI Key: XRQSPUXANRGDAV-UHFFFAOYSA-N
• Popularity: 59 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

• 42079-78-7
• 5-methoxy-2-phenylchromen-4-one
• 5-methoxy-2-phenyl-4h-chromen-4-one
• 5-Methoxy-2-phenyl-4-benzopyrone
• CHEMBL16685
• 4H-1-Benzopyran-4-one, 5-methoxy-2-phenyl-
• EINECS 255-652-0
• 5-Methoxy-2-phenyl-chromen-4-one
• MFCD00016942
• ST069360
• D0V5HF
• Oprea1_842256
• Oprea1_859852
• BIDD:ER0473
• ghl.PD_Mitscher_leg0.1155
• MEGxp0_001704
• SCHEMBL1629391
• ACon1_000175
• DTXSID40194917
• CHEBI:181154
• XRQSPUXANRGDAV-UHFFFAOYSA-N
• BDBM50296862
• s4782
• AKOS000599908
• CCG-208437
• NCGC00142613-01
• NCGC00142613-02
• NCGC00142613-03
• NCGC00180810-01
• AS-62240
• PD056554
• HY-107790
• CS-0030664
• FT-0620566
• M2365
• T72452
• SR-05000002253
• SR-05000002253-2
• BRD-K81383664-001-01-2
• ethyl4-(2-fluorophenyl)-2-methylpyrimidine-5-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8641	86.41%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7381	73.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9596	95.96%
OATP1B3 inhibitior	+	0.9972	99.72%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5926	59.26%
P-glycoprotein inhibitior	+	0.7367	73.67%
P-glycoprotein substrate	-	0.9061	90.61%
CYP3A4 substrate	-	0.5322	53.22%
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	-	0.5918	59.18%
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	+	0.5979	59.79%
Skin irritation	-	0.5383	53.83%
Skin corrosion	-	0.9839	98.39%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4378	43.78%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.9458	94.58%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.6028	60.28%
Acute Oral Toxicity (c)	III	0.8488	84.88%
Estrogen receptor binding	+	0.9651	96.51%
Androgen receptor binding	+	0.8968	89.68%
Thyroid receptor binding	+	0.6480	64.80%
Glucocorticoid receptor binding	+	0.8599	85.99%
Aromatase binding	+	0.9285	92.85%
PPAR gamma	+	0.8622	86.22%
Honey bee toxicity	-	0.7941	79.41%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
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+]	35481.3 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM	Potency	via CMAUP
CHEMBL1871	P10275	Androgen Receptor	8700 nM	IC50	PMID: 19592245
CHEMBL4096	P04637	Cellular tumor antigen p53	7943.3 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	44668.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.89%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.65%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.52%	98.95%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	94.09%	94.03%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.25%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.29%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.16%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.86%	95.50%
CHEMBL1907	P15144	Aminopeptidase N	87.70%	93.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.94%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.54%	97.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.35%	93.99%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.87%	92.08%
CHEMBL1255126	O15151	Protein Mdm4	85.49%	90.20%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.73%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.69%	96.00%
CHEMBL2535	P11166	Glucose transporter	82.22%	98.75%

Plants that contains it

• Imperata cylindrica

Cross-Links

• PubChem: 94525
• NPASS: NPC41721
• ChEMBL: CHEMBL16685