5-Hydroxyflavone

Details

• Internal ID: 77c860ec-c1aa-4a70-a7f7-3b38ec443f47
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 5-hydroxy-2-phenylchromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=CC(=O)C3=C(C=CC=C3O2)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=CC(=O)C3=C(C=CC=C3O2)O
• InChI: InChI=1S/C15H10O3/c16-11-7-4-8-13-15(11)12(17)9-14(18-13)10-5-2-1-3-6-10/h1-9,16H
• InChI Key: IYBLVRRCNVHZQJ-UHFFFAOYSA-N
• Popularity: 183 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24 g/mol
• Exact Mass: 238.062994177 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 491-78-1
• Primuletin
• 5-hydroxy-2-phenylchromen-4-one
• 5-hydroxy-2-phenyl-4H-chromen-4-one
• NSC-26745
• 5-Hydroxy-2-phenylchromone
• 5-Hydroxy-2-phenyl-4-benzopyrone
• 5-Hydroxy-2-phenyl-chromen-4-one
• NSC 26745
• CHEMBL16807
• MLS002639146
• 378AE9MHL3
• NSC26745
• EINECS 207-743-1
• 4H-1-Benzopyran-4-one, 5-hydroxy-2-phenyl-
• Primuliten
• 5-hydroxy-flavone
• MFCD00016944
• 4H-1-Benzopyran-4-one,5-hydroxy-2-phenyl-
• D06YKU
• HYDROXYFLAVONE, 5-
• UNII-378AE9MHL3
• Oprea1_688541
• 5-Hydroxyflavone, >=97%
• FLAVONE, 5-HYDROXY-
• BIDD:ER0489
• SCHEMBL158303
• SPECTRUM1501197
• MEGxp0_001696
• ACon1_001958
• IYBLVRRCNVHZQJ-UHFFFAOYSA-
• DTXSID90197690
• CHEBI:172638
• HMS3749C13
• CS-B1697
• BDBM50049385
• LMPK12110099
• AKOS015856472
• CCG-214308
• NCGC00095329-01
• NCGC00095329-02
• NCGC00095329-03
• NCGC00179967-01
• HY-22024
• SMR001490542
• FT-0754935
• H1238
• C13276
• EN300-7408327
• SR-05000002480
• 5-HYDROXY-2-PHENYL-4H-1-BENZOPYRAN-4-ONE
• SR-05000002480-1
• BRD-K08048246-001-01-8
• BRD-K08048246-001-03-4
• Q63408974
• 66585-06-6
• InChI=1/C15H10O3/c16-11-7-4-8-13-15(11)12(17)9-14(18-13)10-5-2-1-3-6-10/h1-9,16H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.4926	49.26%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6768	67.68%
OATP2B1 inhibitior	-	0.7258	72.58%
OATP1B1 inhibitior	+	0.9687	96.87%
OATP1B3 inhibitior	+	0.9917	99.17%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5294	52.94%
P-glycoprotein inhibitior	-	0.6968	69.68%
P-glycoprotein substrate	-	0.9633	96.33%
CYP3A4 substrate	-	0.6268	62.68%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.5182	51.82%
CYP2C9 inhibition	+	0.6033	60.33%
CYP2C19 inhibition	+	0.7571	75.71%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	+	0.9393	93.93%
CYP2C8 inhibition	-	0.6068	60.68%
CYP inhibitory promiscuity	-	0.6097	60.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.4605	46.05%
Eye corrosion	-	0.9635	96.35%
Eye irritation	+	0.9165	91.65%
Skin irritation	+	0.7177	71.77%
Skin corrosion	-	0.9915	99.15%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8393	83.93%
Micronuclear	+	0.7559	75.59%
Hepatotoxicity	+	0.5283	52.83%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.5795	57.95%
Acute Oral Toxicity (c)	III	0.6941	69.41%
Estrogen receptor binding	+	0.9785	97.85%
Androgen receptor binding	+	0.8592	85.92%
Thyroid receptor binding	+	0.7152	71.52%
Glucocorticoid receptor binding	+	0.9002	90.02%
Aromatase binding	+	0.9591	95.91%
PPAR gamma	+	0.9600	96.00%
Honey bee toxicity	-	0.9058	90.58%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8148	81.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL1871	P10275	Androgen Receptor	831.76 nM; 840 nM; 300 nM	IC50; IC50; IC50	PMID: 23611768; PMID: 23611768; via Super-PRED
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	19952.6 nM	Potency	via CMAUP
CHEMBL2231	P04798	Cytochrome P450 1A1	4030 nM	IC50	PMID: 23600958
CHEMBL3356	P05177	Cytochrome P450 1A2	310 nM	IC50	PMID: 23600958
CHEMBL4878	Q16678	Cytochrome P450 1B1	210 nM	IC50	via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	6309.6 nM; 19952.6 nM; 6309.6 nM; 19952.6 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	31622.8 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	97.98%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.61%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.90%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.47%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.05%	93.99%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.80%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.76%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.30%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.18%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.51%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.94%	94.62%
CHEMBL3194	P02766	Transthyretin	81.70%	90.71%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	81.29%	92.08%

Plants that contains it

• Anthocleista grandiflora
• Chamaemelum nobile
• Conchocarpus heterophyllus
• Helleborus orientalis
• Hypoestes serpens
• Lespedeza homoloba
• Lolium perenne
• Lophomyrtus bullata
• Picradeniopsis multiflora
• Primula denticulata
• Primula farinosa

Cross-Links

• PubChem: 68112
• NPASS: NPC197425
• ChEMBL: CHEMBL16807
• LOTUS: LTS0268543
• wikiData: Q63408974