7-Hydroxyflavone

Details

• Internal ID: 0e223b20-e089-4285-997e-91a9ef826337
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 7-hydroxy-2-phenylchromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C=C3)O
• InChI: InChI=1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H
• InChI Key: MQGPSCMMNJKMHQ-UHFFFAOYSA-N
• Popularity: 283 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: 3.60
• Atomic LogP (AlogP): 3.17
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 6665-86-7
• 7-Hydroxy-2-phenyl-4H-chromen-4-one
• 7-hydroxy-2-phenylchromen-4-one
• 4H-1-Benzopyran-4-one, 7-hydroxy-2-phenyl-
• Flavone, 7-hydroxy-
• 7-Hydroxy-2-phenyl-4-benzopyrone
• 7-Hydroxy-2-phenyl-chromen-4-one
• NSC-94258
• 4H-1-Benzopyran-4-one, 7-hydroxy-
• NSC 94258
• EINECS 229-705-3
• MFCD00006835
• UNII-ZE72458E4L
• MLS002695239
• CHEBI:2268
• CHEMBL276915
• ZE72458E4L
• NSC94258
• 7-hydroxy flavone
• SR-01000359106
• 7-Hydroxyflavone, 11
• 7-Hydroxy-flavone, 5a
• D01KKU
• HYDROXYFLAVONE, 7-
• Oprea1_774070
• 7-Hydroxyflavone, >=98%
• BIDD:ER0599
• SCHEMBL312148
• MEGxp0_001698
• DTXSID3022328
• ACon1_000093
• BDBM26664
• HY-N7108
• BBL100067
• s5380
• STL511043
• AKOS000599907
• CCG-208393
• NCGC00163568-01
• NCGC00163568-02
• NCGC00168801-01
• 7-Hydroxy-2-phenyl-4H-chromen-4-one #
• AS-19983
• SMR000112319
• SBI-0207061.P001
• 7--HYDROXY-2-PHENYL-4-BENZOPYRONE
• LS-195383
• 4-Hydroxy-2-phenyl-7H-1-benzopyran-7-one
• CS-0081150
• FT-0621434
• H0852
• H-5100
• SR-01000359106-1
• SR-01000359106-3
• BRD-K56450366-001-01-1
• BRD-K56450366-001-03-7
• Q27105601

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	-	0.8704	87.04%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6768	67.68%
OATP2B1 inhibitior	-	0.7273	72.73%
OATP1B1 inhibitior	+	0.9148	91.48%
OATP1B3 inhibitior	+	0.9917	99.17%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7045	70.45%
P-glycoprotein inhibitior	-	0.7514	75.14%
P-glycoprotein substrate	-	0.8852	88.52%
CYP3A4 substrate	-	0.5808	58.08%
CYP2C9 substrate	-	0.8209	82.09%
CYP2D6 substrate	-	0.8000	80.00%
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	+	0.6675	66.75%
CYP inhibitory promiscuity	-	0.6097	60.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.4605	46.05%
Eye corrosion	-	0.9635	96.35%
Eye irritation	+	0.9783	97.83%
Skin irritation	+	0.7177	71.77%
Skin corrosion	-	0.9915	99.15%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8427	84.27%
Micronuclear	+	0.7559	75.59%
Hepatotoxicity	+	0.5825	58.25%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.6400	64.00%
Acute Oral Toxicity (c)	III	0.6941	69.41%
Estrogen receptor binding	+	0.9548	95.48%
Androgen receptor binding	+	0.9536	95.36%
Thyroid receptor binding	+	0.6776	67.76%
Glucocorticoid receptor binding	+	0.9458	94.58%
Aromatase binding	+	0.9574	95.74%
PPAR gamma	+	0.9055	90.55%
Honey bee toxicity	-	0.8662	86.62%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8148	81.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	8300 nM; 160000 nM	IC50; IC50	PMID: 26529431; PMID: 26529431
CHEMBL1900	P15121	Aldose reductase	12300 nM	IC50	PMID: 26529431
CHEMBL261	P00915	Carbonic anhydrase I	3370 nM; 3430 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL205	P00918	Carbonic anhydrase II	2240 nM; 2320 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL3594	Q16790	Carbonic anhydrase IX	4850 nM; 4920 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL3242	O43570	Carbonic anhydrase XII	8400 nM; 8510 nM	Ki; Ki	PMID: 22487176; PMID: 22487176
CHEMBL1978	P11511	Cytochrome P450 19A1	30.5 nM; 30.5 nM	IC50; IC50	PMID: 20413308; via Super-PRED
CHEMBL3356	P05177	Cytochrome P450 1A2	240 nM	IC50	PMID: 20832301
CHEMBL4878	Q16678	Cytochrome P450 1B1	250 nM	IC50	via Super-PRED
CHEMBL3181	P14061	Estradiol 17-beta-dehydrogenase 1	5250 nM	IC50	PMID: 18533708
CHEMBL1929	P47989	Xanthine dehydrogenase	38000 nM	IC50	PMID: 9461655

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.61%	91.11%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.34%	83.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.14%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.84%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.20%	89.00%
CHEMBL242	Q92731	Estrogen receptor beta	88.81%	98.35%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.62%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.23%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.59%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.20%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.18%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.16%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.85%	94.00%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	80.73%	92.08%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.02%	94.23%

Plants that contains it

• Astragalus microcephalus
• Berberis dictyota
• Jasminum sambac
• Lawsonia inermis
• Muntingia calabura

Cross-Links

• PubChem: 5281894
• NPASS: NPC57601
• ChEMBL: CHEMBL276915
• LOTUS: LTS0135437
• wikiData: Q27105601