5,6-Dihydroxy-4'-methoxyflavanone

Details

• Internal ID: 2199c0e8-cb1f-4dbf-ba54-7def5a76bb87
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: 5,6-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2CC(=O)C3=C(O2)C=CC(=C3O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2CC(=O)C3=C(O2)C=CC(=C3O)O
• InChI: InChI=1S/C16H14O5/c1-20-10-4-2-9(3-5-10)14-8-12(18)15-13(21-14)7-6-11(17)16(15)19/h2-7,14,17,19H,8H2,1H3
• InChI Key: ONKIXTJNUUWOHL-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEBI:178317
• LMPK12140103
• 5,6-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9145	91.45%
Caco-2	-	0.6348	63.48%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7935	79.35%
OATP2B1 inhibitior	-	0.8650	86.50%
OATP1B1 inhibitior	+	0.9285	92.85%
OATP1B3 inhibitior	+	0.9963	99.63%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8414	84.14%
P-glycoprotein inhibitior	-	0.8660	86.60%
P-glycoprotein substrate	-	0.9584	95.84%
CYP3A4 substrate	+	0.5256	52.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7613	76.13%
CYP3A4 inhibition	-	0.6935	69.35%
CYP2C9 inhibition	+	0.7420	74.20%
CYP2C19 inhibition	+	0.7729	77.29%
CYP2D6 inhibition	-	0.6885	68.85%
CYP1A2 inhibition	+	0.9020	90.20%
CYP2C8 inhibition	-	0.8308	83.08%
CYP inhibitory promiscuity	+	0.5106	51.06%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5302	53.02%
Eye corrosion	-	0.9854	98.54%
Eye irritation	+	0.5296	52.96%
Skin irritation	-	0.6553	65.53%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6287	62.87%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	-	0.7310	73.10%
skin sensitisation	-	0.9304	93.04%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.4606	46.06%
Acute Oral Toxicity (c)	III	0.5877	58.77%
Estrogen receptor binding	+	0.7429	74.29%
Androgen receptor binding	+	0.7684	76.84%
Thyroid receptor binding	+	0.7192	71.92%
Glucocorticoid receptor binding	+	0.6829	68.29%
Aromatase binding	+	0.6873	68.73%
PPAR gamma	+	0.8223	82.23%
Honey bee toxicity	-	0.8988	89.88%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7979	79.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.16%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.38%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.29%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.45%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.36%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.38%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.13%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.52%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.15%	99.23%
CHEMBL4208	P20618	Proteasome component C5	89.03%	90.00%
CHEMBL2581	P07339	Cathepsin D	86.64%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.05%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.22%	93.99%

Plants that contains it

• Artemisia campestris

Cross-Links

• PubChem: 14353344
• LOTUS: LTS0015346
• wikiData: Q105216766