Dillenetin

Details

• Internal ID: 83dadfd5-2ece-4a9e-8a95-2c8ae4d5af77
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 2-(3,4-dimethoxyphenyl)-3,5,7-trihydroxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)OC
• InChI: InChI=1S/C17H14O7/c1-22-11-4-3-8(5-12(11)23-2)17-16(21)15(20)14-10(19)6-9(18)7-13(14)24-17/h3-7,18-19,21H,1-2H3
• InChI Key: MHALJYZRPGYQSI-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₇
• Molecular Weight: 330.29 g/mol
• Exact Mass: 330.07395278 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.59
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 3306-29-4
• 3,4-Dimethoxy-3,5,7-trihydroxyflavone
• 3',4'-Dimethoxyquercetin
• 2-(3,4-dimethoxyphenyl)-3,5,7-trihydroxychromen-4-one
• 3',4'-Di-O-methylquercetin
• UNII-S3Z5LJ2T0Y
• S3Z5LJ2T0Y
• 2-(3,4-dimethoxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,7-trihydroxy-
• 3,5,7-Trihydroxy-3',4'-dimethoxyflavone
• 2-(3,4-Dimethoxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
• 3',4'-O-dimethylquercetin
• quercetin 3',4'-dimethyl ether
• 3',4'-dimethylquercetin
• SCHEMBL3211188
• CHEMBL2043330
• DTXSID80186715
• CHEBI:174458
• LMPK12112411
• 5,7-Dihydroxy-3',4'-dimethoxyflavonol
• QUERCETIN-3',4'-DIMETHYL ETHER
• 3,5,7-trihydroxy-3',4'-dimethoxy flavone
• FT-0756769
• Q27288547
• 2-(3,4-Dimethoxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9440	94.40%
Caco-2	+	0.6530	65.30%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6642	66.42%
OATP2B1 inhibitior	-	0.6756	67.56%
OATP1B1 inhibitior	+	0.8767	87.67%
OATP1B3 inhibitior	+	0.9261	92.61%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6354	63.54%
P-glycoprotein inhibitior	+	0.6418	64.18%
P-glycoprotein substrate	-	0.6323	63.23%
CYP3A4 substrate	+	0.5994	59.94%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.7817	78.17%
CYP2C9 inhibition	+	0.6258	62.58%
CYP2C19 inhibition	+	0.8187	81.87%
CYP2D6 inhibition	-	0.6249	62.49%
CYP1A2 inhibition	+	0.8668	86.68%
CYP2C8 inhibition	+	0.9640	96.40%
CYP inhibitory promiscuity	+	0.8459	84.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6581	65.81%
Eye corrosion	-	0.9779	97.79%
Eye irritation	+	0.6477	64.77%
Skin irritation	-	0.6522	65.22%
Skin corrosion	-	0.9396	93.96%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5329	53.29%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9222	92.22%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7821	78.21%
Acute Oral Toxicity (c)	III	0.5920	59.20%
Estrogen receptor binding	+	0.9248	92.48%
Androgen receptor binding	+	0.7634	76.34%
Thyroid receptor binding	+	0.7069	70.69%
Glucocorticoid receptor binding	+	0.9051	90.51%
Aromatase binding	+	0.8239	82.39%
PPAR gamma	+	0.8639	86.39%
Honey bee toxicity	-	0.8791	87.91%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.8636	86.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.89%	94.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.10%	96.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.03%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.81%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.80%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.07%	98.95%
CHEMBL3194	P02766	Transthyretin	91.53%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.48%	95.56%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	87.63%	98.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.95%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.30%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.28%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.51%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.41%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	83.74%	94.73%
CHEMBL1255126	O15151	Protein Mdm4	83.70%	90.20%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	83.31%	83.10%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.22%	85.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.92%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.26%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.05%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	81.37%	95.64%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.34%	93.65%
CHEMBL2424	Q04760	Glyoxalase I	81.18%	91.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.81%	93.99%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	80.40%	98.21%

Plants that contains it

• Arnica chamissonis
• Balsamorhiza deltoidea
• Biancaea sappan
• Corydalis paczoskii
• Corydalis solida
• Dillenia indica
• Lycopodiella cernua
• Pogostemon cablin
• Sigesbeckia glabrescens
• Sigesbeckia pubescens

Cross-Links

• PubChem: 5487855
• NPASS: NPC159103
• ChEMBL: CHEMBL2043330
• LOTUS: LTS0093235
• wikiData: Q105186338