3,5-Dihydroxyflavone

Details

• Internal ID: c249f0b4-62cb-4a84-af14-9cac233187d3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3,5-dihydroxy-2-phenylchromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=C(C(=O)C3=C(C=CC=C3O2)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=C(C(=O)C3=C(C=CC=C3O2)O)O
• InChI: InChI=1S/C15H10O4/c16-10-7-4-8-11-12(10)13(17)14(18)15(19-11)9-5-2-1-3-6-9/h1-8,16,18H
• InChI Key: QHYWQIVTVQAKQF-UHFFFAOYSA-N
• Popularity: 144 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24 g/mol
• Exact Mass: 254.05790880 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 6665-69-6
• 3,5-dihydroxy-2-phenyl-4H-chromen-4-one
• 3,5-dihydroxy-2-phenylchromen-4-one
• 3,5,-Dihydroxyflavone
• CHEMBL239276
• dihydroxyflavone
• SCHEMBL290081
• SPECTRUM1505147
• DTXSID30419823
• QHYWQIVTVQAKQF-UHFFFAOYSA-N
• BDBM50222291
• MFCD00143074
• AKOS024285110
• 3,5-dihydroxy-2-phenyl-chromen-4-one
• NCGC00096043-01
• PD000599
• 3,5-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one
• SR-05000002503
• 4H-1-Benzopyran-4-one, 3,5-dihydroxy-2-phenyl-
• SR-05000002503-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	-	0.9144	91.44%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7927	79.27%
OATP2B1 inhibitior	-	0.6942	69.42%
OATP1B1 inhibitior	+	0.9226	92.26%
OATP1B3 inhibitior	+	0.8971	89.71%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6431	64.31%
P-glycoprotein inhibitior	-	0.7642	76.42%
P-glycoprotein substrate	-	0.9090	90.90%
CYP3A4 substrate	-	0.5832	58.32%
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	+	0.6281	62.81%
CYP inhibitory promiscuity	+	0.6528	65.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9894	98.94%
Eye irritation	+	0.9153	91.53%
Skin irritation	+	0.6540	65.40%
Skin corrosion	-	0.9775	97.75%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8935	89.35%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.8370	83.70%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5849	58.49%
Acute Oral Toxicity (c)	II	0.5971	59.71%
Estrogen receptor binding	+	0.9150	91.50%
Androgen receptor binding	+	0.5905	59.05%
Thyroid receptor binding	+	0.7532	75.32%
Glucocorticoid receptor binding	+	0.9110	91.10%
Aromatase binding	+	0.9056	90.56%
PPAR gamma	+	0.9534	95.34%
Honey bee toxicity	-	0.9456	94.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9185	91.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	5623.4 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	3300 nM	IC50	PMID: 17869117
CHEMBL4096	P04637	Cellular tumor antigen p53	3162.3 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	5623.4 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	35481.3 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.57%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.12%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.48%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.92%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.23%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.47%	86.33%
CHEMBL3959	P16083	Quinone reductase 2	87.22%	89.49%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	86.66%	95.72%
CHEMBL1951	P21397	Monoamine oxidase A	84.97%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	84.70%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.89%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.43%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.25%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.20%	93.99%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.24%	94.62%

Plants that contains it

• Anthocleista grandiflora
• Chamaemelum nobile
• Helleborus orientalis
• Hypoestes serpens
• Lespedeza homoloba
• Lolium perenne
• Picradeniopsis multiflora
• Primula farinosa

Cross-Links

• PubChem: 5393151
• NPASS: NPC128216
• ChEMBL: CHEMBL239276