3,7-Dihydroxyflavone

Details

• Internal ID: 8cf0ab39-5358-4068-9076-1865f92273d1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3,7-dihydroxy-2-phenylchromen-4-one
• InChI: InChI=1S/C15H10O4/c16-10-6-7-11-12(8-10)19-15(14(18)13(11)17)9-4-2-1-3-5-9/h1-8,16,18H
• InChI Key: UWQJWDYDYIJWKY-UHFFFAOYSA-N
• Popularity: 71 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: 3.00
• Atomic LogP (AlogP): 2.87
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 492-00-2
• 7-Hydroxyflavonol
• 5-Deoxygalangin
• 3,7-dihydroxy-2-phenylchromen-4-one
• 4H-1-Benzopyran-4-one, 3,7-dihydroxy-2-phenyl-
• 3,7-dihydroxy-flavone
• O948D0K9BQ
• 3,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one
• RefChem:910778
• CHEBI:52267
• 7,3-dihydroxyflavone
• 3,7-dihydroxy-2-phenyl-4H-chromen-4-one
• Resogalangin
• 3,7-dihydroxy-2-phenyl-chromen-4-one
• CHEMBL210276
• MFCD00016790
• 7,3'-dihydroxyflavonol
• SR-01000314616
• SPBio_001803
• 7-Hydroxyflavanol
• Spectrum_001462
• SpecPlus_000778
• Spectrum2_001652
• Spectrum3_001623
• Spectrum4_001767
• Spectrum5_000353
• UNII-O948D0K9BQ
• Oprea1_793720
• BSPBio_003285
• KBioGR_002253
• KBioSS_001942
• DivK1c_006874
• SPECTRUM1504130
• orb1685409
• SCHEMBL2396684
• 7,3/'-DIHYDROXYFLAVONE
• SCHEMBL29625323
• BDBM26660
• KBio1_001818
• KBio2_001942
• KBio2_004510
• KBio2_007078
• KBio3_002505
• DTXSID80197705
• CHEBI:109535
• UWQJWDYDYIJWKY-UHFFFAOYSA-N
• CCG-38768
• LMPK12111545
• AKOS000600301
• 3,7-Dihydroxyflavone; 5-Deoxygalangin
• FD66161
• SDCCGMLS-0066816.P001
• NCGC00095686-01
• NCGC00095686-02
• NCGC00178162-01
• PD001272
• ST092291
• DB-022136
• DB-350680
• CS-0137284
• NS00116344
• A827674
• SR-01000314616-1
• SR-01000314616-2
• BRD-K35133923-001-02-3
• BRD-K35133923-001-03-1
• Q27188682
• HHF

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	-	0.9391	93.91%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7927	79.27%
OATP2B1 inhibitior	-	0.6909	69.09%
OATP1B1 inhibitior	+	0.9374	93.74%
OATP1B3 inhibitior	+	0.8971	89.71%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6293	62.93%
P-glycoprotein inhibitior	-	0.7738	77.38%
P-glycoprotein substrate	-	0.7712	77.12%
CYP3A4 substrate	-	0.5587	55.87%
CYP2C9 substrate	-	0.8209	82.09%
CYP2D6 substrate	-	0.8000	80.00%
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	+	0.7484	74.84%
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	+	0.9679	96.79%
Skin irritation	+	0.6540	65.40%
Skin corrosion	-	0.9775	97.75%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9079	90.79%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8370	83.70%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7083	70.83%
Acute Oral Toxicity (c)	II	0.5971	59.71%
Estrogen receptor binding	+	0.9157	91.57%
Androgen receptor binding	+	0.9119	91.19%
Thyroid receptor binding	+	0.7272	72.72%
Glucocorticoid receptor binding	+	0.9323	93.23%
Aromatase binding	+	0.9208	92.08%
PPAR gamma	+	0.9032	90.32%
Honey bee toxicity	-	0.9160	91.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9185	91.85%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	19952.6 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	25118.9 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	15848.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	39810.7 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.23%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.91%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.45%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.84%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.78%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.71%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.02%	91.49%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.65%	94.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.34%	99.15%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.05%	83.57%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.12%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.49%	94.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	81.20%	92.67%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.48%	94.23%

Plants that contains it

• Zuccagnia punctata

Cross-Links

• PubChem: 5393152
• NPASS: NPC299379
• ChEMBL: CHEMBL210276
• LOTUS: LTS0164900
• wikiData: Q27188682