3',4'-Dimethoxyflavone

Details

• Internal ID: 717c2aa9-f192-425b-bb64-42a668d1c7d3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: 2-(3,4-dimethoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=CC(=O)C3=CC=CC=C3O2)OC
• InChI: InChI=1S/C17H14O4/c1-19-15-8-7-11(9-17(15)20-2)16-10-13(18)12-5-3-4-6-14(12)21-16/h3-10H,1-2H3
• InChI Key: ZGHORMOOTZTQFL-UHFFFAOYSA-N
• Popularity: 69 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.29 g/mol
• Exact Mass: 282.08920892 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.48
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 4143-62-8
• 2-(3,4-dimethoxyphenyl)-4H-chromen-4-one
• 2-(3,4-dimethoxyphenyl)chromen-4-one
• CHEMBL91153
• KBio2_004087
• MFCD00143009
• Spectrum_001039
• 2-(3,4-Dimethoxy-phenyl)-chromen-4-one
• SpecPlus_000555
• Spectrum2_000709
• Spectrum4_001893
• Spectrum5_000546
• 3/',4/'-Dimethoxyflavone
• Oprea1_098805
• KBioGR_002451
• KBioSS_001519
• DivK1c_006651
• SPECTRUM1500735
• 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-
• SPBio_000897
• SCHEMBL1675954
• 3-,4--DIMETHOXYFLAVONE
• KBio1_001595
• KBio2_001519
• KBio2_006655
• DTXSID50350946
• ZGHORMOOTZTQFL-UHFFFAOYSA-N
• HY-N8572
• BDBM50420209
• CCG-40034
• STK899809
• AKOS002279678
• SDCCGMLS-0066648.P001
• NCGC00095629-01
• PD171572
• CS-0148635
• D4794
• FT-0614346
• T70897
• A825556
• AN-829/41499278
• SR-01000471680
• SR-01000471680-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9912	99.12%
Caco-2	+	0.8942	89.42%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7084	70.84%
OATP2B1 inhibitior	-	0.8629	86.29%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9941	99.41%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6365	63.65%
P-glycoprotein inhibitior	+	0.9316	93.16%
P-glycoprotein substrate	-	0.7680	76.80%
CYP3A4 substrate	+	0.5624	56.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7654	76.54%
CYP3A4 inhibition	+	0.7725	77.25%
CYP2C9 inhibition	+	0.7254	72.54%
CYP2C19 inhibition	+	0.9410	94.10%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9711	97.11%
CYP2C8 inhibition	+	0.7193	71.93%
CYP inhibitory promiscuity	+	0.8566	85.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5823	58.23%
Eye corrosion	-	0.9571	95.71%
Eye irritation	-	0.5085	50.85%
Skin irritation	-	0.6684	66.84%
Skin corrosion	-	0.9798	97.98%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7071	70.71%
Micronuclear	+	0.8259	82.59%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.9303	93.03%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5735	57.35%
Acute Oral Toxicity (c)	II	0.5367	53.67%
Estrogen receptor binding	+	0.9476	94.76%
Androgen receptor binding	+	0.8956	89.56%
Thyroid receptor binding	+	0.7461	74.61%
Glucocorticoid receptor binding	+	0.8667	86.67%
Aromatase binding	+	0.7543	75.43%
PPAR gamma	+	0.7132	71.32%
Honey bee toxicity	-	0.7756	77.56%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9143	91.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	31622.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	15848.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	3548.1 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	12589.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	4466.8 nM	Potency	via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	1200 nM	IC50	PMID: 15240100
CHEMBL1293232	Q16637	Survival motor neuron protein	10000 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	4466.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.32%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.78%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.15%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.72%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.37%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.05%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.86%	89.00%
CHEMBL1255126	O15151	Protein Mdm4	85.03%	90.20%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.48%	97.14%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.41%	94.03%
CHEMBL1907	P15144	Aminopeptidase N	84.20%	93.31%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.82%	95.50%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.77%	85.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.14%	99.23%

Plants that contains it

• Lawsonia inermis
• Primula veris
• Primula veris subsp. macrocalyx

Cross-Links

• PubChem: 688674
• NPASS: NPC77955
• ChEMBL: CHEMBL91153
• LOTUS: LTS0182841
• wikiData: Q82127014