3-Hydroxyflavone

Details

• Internal ID: 57f1af4f-9b2f-486e-b049-5dbc60f78276
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3-hydroxy-2-phenylchromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3O2)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3O2)O
• InChI: InChI=1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H
• InChI Key: HVQAJTFOCKOKIN-UHFFFAOYSA-N
• Popularity: 12,935 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: 3.40
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Flavonol
• 577-85-5
• 3-Hydroxy-2-phenyl-4H-chromen-4-one
• Flavon-3-ol
• 3-Hydroxy-2-phenylchromone
• 4H-1-Benzopyran-4-one, 3-hydroxy-2-phenyl-
• FLAVONE, 3-HYDROXY-
• 3-hydroxy-2-phenylchromen-4-one
• 3-HF
• FLAVONE,3-HYDROXY-
• UNII-ZTG9LSS5QH
• ZTG9LSS5QH
• NSC57653
• EINECS 209-416-9
• MFCD00006832
• NSC 57653
• NSC 58585
• NSC-57653
• CHEBI:5078
• CHEMBL294009
• 3-hydroxy-2-phenyl-4H-1-benzopyran-4-one
• HSDB 7572
• flavonols
• NSC58585
• NSC-58585
• NSC-58586
• NSC-58587
• SR-01000401360
• 3-hydroxyflavon
• 3-hydroxy-2-phenyl-chromen-4-one
• Spectrum_000328
• SpecPlus_000831
• Spectrum2_001392
• Spectrum3_001432
• Spectrum4_001845
• Spectrum5_000350
• Oprea1_038914
• Oprea1_692205
• SCHEMBL20246
• 3-Hydroxyflavone, >=98%
• 4-Hydroxy-3-oxylatoflavylium
• BSPBio_003164
• KBioGR_002250
• KBioSS_000808
• MLS002207277
• BIDD:ER0553
• DivK1c_006927
• SPECTRUM1501012
• SPBio_001404
• F0013-0884
• MEGxp0_001695
• 3-HYDROXYFLAVONE [HSDB]
• DTXSID4060365
• ACon1_000167
• KBio1_001871
• KBio2_000808
• KBio2_003376
• KBio2_005944
• KBio3_002384
• HMS3740M15
• KUC106685N
• WLN: T66 BO EVJ CR& DQ
• BDBM50187668
• CCG-38858
• NCI-57653
• s4790
• AKOS000599906
• SDCCGMLS-0066736.P001
• NCGC00095653-01
• NCGC00095653-02
• NCGC00095653-03
• 3-Hydroxy-2-phenyl-4H-chromen-4-one #
• AS-19638
• LS-69007
• SMR000112317
• SY048803
• KSC-11-207-16
• HY-107825
• CS-0030701
• EU-0001678
• FT-0615841
• H0379
• VU0053575-3
• C01495
• D71219
• H-5000
• 3-Hydroxy-2-phenyl-4H-1-benzopyran-4-one, 9CI
• A869585
• Q5919049
• SR-01000401360-1
• SR-01000401360-2
• BRD-K55150756-001-05-7
• B48D3495-6D21-4742-8A87-D3DE07DC9554

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9946	99.46%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8073	80.73%
OATP2B1 inhibitior	-	0.7266	72.66%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9640	96.40%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6102	61.02%
P-glycoprotein inhibitior	-	0.7436	74.36%
P-glycoprotein substrate	-	0.9270	92.70%
CYP3A4 substrate	-	0.5674	56.74%
CYP2C9 substrate	-	0.8209	82.09%
CYP2D6 substrate	-	0.8000	80.00%
CYP3A4 inhibition	-	0.8518	85.18%
CYP2C9 inhibition	+	0.7911	79.11%
CYP2C19 inhibition	+	0.7050	70.50%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	+	0.9066	90.66%
CYP2C8 inhibition	-	0.6354	63.54%
CYP inhibitory promiscuity	-	0.5266	52.66%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5583	55.83%
Eye corrosion	-	0.9835	98.35%
Eye irritation	+	0.9171	91.71%
Skin irritation	+	0.7668	76.68%
Skin corrosion	-	0.9870	98.70%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8615	86.15%
Micronuclear	+	0.8418	84.18%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.7567	75.67%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6275	62.75%
Acute Oral Toxicity (c)	II	0.4611	46.11%
Estrogen receptor binding	+	0.8496	84.96%
Androgen receptor binding	+	0.6436	64.36%
Thyroid receptor binding	+	0.7565	75.65%
Glucocorticoid receptor binding	+	0.8891	88.91%
Aromatase binding	+	0.9192	91.92%
PPAR gamma	+	0.9183	91.83%
Honey bee toxicity	-	0.9416	94.16%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8903	89.03%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	23500 nM	IC50	PMID: 19592245
CHEMBL261	P00915	Carbonic anhydrase I	5210 nM; 5100 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL205	P00918	Carbonic anhydrase II	9300 nM; 9200 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL3594	Q16790	Carbonic anhydrase IX	5540 nM; 5630 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL3242	O43570	Carbonic anhydrase XII	6590 nM; 6650 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4878	Q16678	Cytochrome P450 1B1	90 nM	IC50	via Super-PRED
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	25118.9 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	98.96%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.07%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.87%	99.23%
CHEMBL2581	P07339	Cathepsin D	92.70%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.51%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.07%	94.23%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	87.01%	95.72%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.36%	94.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.21%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.68%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.54%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	80.66%	94.73%

Plants that contains it

• Acacia melanoxylon
• Chelidonium majus
• Chrysanthemum morifolium
• Cichorium intybus
• Cichorium pumilum
• Ginkgo biloba

Cross-Links

• PubChem: 11349
• NPASS: NPC93730
• ChEMBL: CHEMBL294009
• LOTUS: LTS0190891
• wikiData: Q5919049