5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Details

• Internal ID: f574c5be-adab-40ed-9c81-605dd01c8534
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O
• InChI: InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3
• InChI Key: AIONOLUJZLIMTK-UHFFFAOYSA-N
• Popularity: 299 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• rac-Hesperetin
• (Rac)-Hesperetin
• (R)-Hesperetin
• (+/-)-Hesperetin
• 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• NSC641520
• 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• MLS002667896
• 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
• (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone
• hesperetine
• 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone
• MFCD00075646
• Hesperetin, >=95%
• CHEMBL88169
• SCHEMBL765368
• Hesperetin, analytical standard
• ACon1_002327
• CHEBI:95167
• HY-N0168A
• DTXSID70859446
• DTXSID80274404
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
• HMS3373J01
• HMS3656C03
• NSC57654
• 3',7-Trihydroxy-4'-methoxyflavanone
• 5,3'-Trihydroxy-4'-methoxyflavanone
• AKOS015995360
• (+/-)-Hesperetin, analytical standard
• Flavanone,5,7-trihydroxy-4'-methoxy-
• NSC-641520
• NCGC00095618-01
• NCGC00095618-02
• AS-11672
• NCI60_014043
• SMR001557653
• SY057338
• XH167423
• CS-0111125
• FT-0626940
• EN300-23521574
• BRD-A44482398-001-01-3
• Q27166968
• FE387278-0643-4EBB-902D-C81B1FCDE1F8
• 5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one
• 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one
• 4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9028	90.28%
Caco-2	+	0.8207	82.07%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6551	65.51%
OATP2B1 inhibitior	-	0.5904	59.04%
OATP1B1 inhibitior	+	0.9581	95.81%
OATP1B3 inhibitior	+	0.9701	97.01%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8294	82.94%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	-	0.9026	90.26%
CYP3A4 substrate	+	0.5487	54.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	+	0.6510	65.10%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.4504	45.04%
CYP inhibitory promiscuity	+	0.7998	79.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5775	57.75%
Eye corrosion	-	0.9853	98.53%
Eye irritation	+	0.9629	96.29%
Skin irritation	-	0.6488	64.88%
Skin corrosion	-	0.9295	92.95%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7259	72.59%
Micronuclear	+	0.8459	84.59%
Hepatotoxicity	-	0.6218	62.18%
skin sensitisation	-	0.9253	92.53%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6431	64.31%
Acute Oral Toxicity (c)	III	0.5979	59.79%
Estrogen receptor binding	+	0.7878	78.78%
Androgen receptor binding	+	0.5318	53.18%
Thyroid receptor binding	+	0.7151	71.51%
Glucocorticoid receptor binding	+	0.8091	80.91%
Aromatase binding	+	0.6516	65.16%
PPAR gamma	+	0.8556	85.56%
Honey bee toxicity	-	0.7997	79.97%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5449	54.49%
Fish aquatic toxicity	+	0.7222	72.22%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3729	P22748	Carbonic anhydrase IV	102.1 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	3.3 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	454.1 nM	Ki	via Super-PRED
CHEMBL4878	Q16678	Cytochrome P450 1B1	511 nM	IC50	via Super-PRED
CHEMBL284	P27487	Dipeptidyl peptidase IV	280 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.84%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.43%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.41%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.27%	94.00%
CHEMBL2581	P07339	Cathepsin D	89.73%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.37%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.29%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.03%	99.23%
CHEMBL4208	P20618	Proteasome component C5	88.22%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.80%	86.33%
CHEMBL3194	P02766	Transthyretin	86.86%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.69%	95.89%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.51%	96.12%
CHEMBL2535	P11166	Glucose transporter	85.05%	98.75%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.77%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.78%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.14%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.57%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.26%	97.14%

Plants that contains it

• Artemisia xanthochroa
• Brickellia vernicosa
• Chrysothamnus viscidiflorus
• Citrus × aurantium
• Dalbergia parviflora

Cross-Links

• PubChem: 3593
• LOTUS: LTS0070100
• wikiData: Q27166968