3,5-Dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 92dc1faa-f523-4e02-b1c4-bcac891bc3d7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3,5-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=C2C(=C1)OC(=C(C2=O)O)C3=CC=C(C=C3)O)O
• SMILES (Isomeric): C1=CC(=C2C(=C1)OC(=C(C2=O)O)C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C15H10O5/c16-9-6-4-8(5-7-9)15-14(19)13(18)12-10(17)2-1-3-11(12)20-15/h1-7,16-17,19H
• InChI Key: ZLNYYIOAMRCRGD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24 g/mol
• Exact Mass: 270.05282342 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 86788-60-5
• 3,5-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
• CHEMBL2024312
• SCHEMBL10335363
• DTXSID90419824
• ZLNYYIOAMRCRGD-UHFFFAOYSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	-	0.9495	94.95%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7927	79.27%
OATP2B1 inhibitior	-	0.6400	64.00%
OATP1B1 inhibitior	+	0.8450	84.50%
OATP1B3 inhibitior	+	0.8971	89.71%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5545	55.45%
P-glycoprotein inhibitior	-	0.8725	87.25%
P-glycoprotein substrate	-	0.8250	82.50%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.7012	70.12%
CYP2C9 inhibition	+	0.9776	97.76%
CYP2C19 inhibition	+	0.7715	77.15%
CYP2D6 inhibition	-	0.9179	91.79%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.8539	85.39%
CYP inhibitory promiscuity	+	0.6528	65.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9894	98.94%
Eye irritation	+	0.9304	93.04%
Skin irritation	+	0.6540	65.40%
Skin corrosion	-	0.9775	97.75%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9202	92.02%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.8370	83.70%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5540	55.40%
Acute Oral Toxicity (c)	II	0.5971	59.71%
Estrogen receptor binding	+	0.8523	85.23%
Androgen receptor binding	+	0.8114	81.14%
Thyroid receptor binding	+	0.6654	66.54%
Glucocorticoid receptor binding	+	0.9082	90.82%
Aromatase binding	+	0.8853	88.53%
PPAR gamma	+	0.9472	94.72%
Honey bee toxicity	-	0.9287	92.87%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9185	91.85%

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	96.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.23%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.33%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.02%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.95%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.48%	99.23%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.82%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	88.80%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.79%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.67%	86.33%
CHEMBL3959	P16083	Quinone reductase 2	83.62%	89.49%
CHEMBL1951	P21397	Monoamine oxidase A	82.77%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.74%	94.45%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.21%	83.10%

Plants that contains it

• Celosia argentea

Cross-Links

• PubChem: 5393154
• NPASS: NPC248872
• ChEMBL: CHEMBL2024312