Hesperetin

Details

• Internal ID: a80415d4-ea19-43fe-b94a-426a023d27c6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: (2S)-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)[C@@H]2CC(=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/t14-/m0/s1
• InChI Key: AIONOLUJZLIMTK-AWEZNQCLSA-N
• Popularity: 2,342 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

• 520-33-2
• Hesperitin
• 3',5,7-Trihydroxy-4'-methoxyflavanone
• (-)-hesperetin
• (S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
• YSO2
• 5,7,3'-Trihydroxy-4'-methoxyflavanone
• Cyanidanon 4'-methyl ether 1626
• 41001-90-5
• NSC 57654
• Prestwick_908
• (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• (-)-(S)-hesperetin
• EINECS 208-290-2
• NSC-57654
• UNII-Q9Q3D557F1
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-
• Eriodictyol 4'-monomethyl ether
• CHEBI:28230
• Q9Q3D557F1
• TNP00238
• (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one
• (S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone
• (2S)-hesperetin
• (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one
• (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
• Flavanone, 3',5,7-trihydroxy-4'-methoxy- (VAN)
• MFCD00075646
• (2s)-5,7-Dihydroxy-2-(3-Hydroxy-4-Methoxyphenyl)-2,3-Dihydro-4h-1-Benzopyran-4-One
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
• Hesperitine
• (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (Hesperetin)
• 6JP
• (+-)-Hesperetin
• 4'-Methoxy-3',5,7-trihydroxyflavanone
• Diosmin EP Impurity G
• Spectrum_000181
• HESPERETIN [MI]
• Prestwick0_000124
• Prestwick1_000124
• Prestwick2_000124
• Prestwick3_000124
• Spectrum2_001793
• Spectrum3_001104
• Spectrum4_001935
• Spectrum5_000683
• HESPERETIN [FHFI]
• HESPERETIN [INCI]
• D07MGA
• 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone
• Oprea1_828704
• SCHEMBL39833
• BSPBio_000168
• BSPBio_002808
• KBioGR_002311
• KBioSS_000661
• SPECTRUM310012
• MLS002154205
• BIDD:ER0512
• DivK1c_001039
• SPBio_001745
• SPBio_002107
• BPBio1_000186
• CHEMBL399121
• DTXSID4022319
• FEMA NO. 4313
• BCBcMAP01_000087
• BDBM23418
• GTPL10953
• HMS503O19
• KBio1_001039
• KBio2_000661
• KBio2_003229
• KBio2_005797
• KBio3_002028
• NINDS_001039
• HMS1568I10
• HMS2095I10
• HMS2230M09
• HMS3649H22
• HMS3884N11
• NP-13
• (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one
• BCP28273
• HY-N0168
• BBL104011
• CCG-38441
• LMPK12140003
• s2308
• STL557824
• AKOS016339567
• AC-7970
• CS-O-13590
• CS-O-30940
• DB01094
• KS-5307
• SDCCGMLS-0066605.P001
• IDI1_001039
• SMP1_000148
• NCGC00016482-01
• NCGC00016482-02
• NCGC00016482-03
• NCGC00016482-04
• NCGC00142415-01
• NCGC00142415-02
• 5,7, 3'-Trihydroxy-4'-methoxyflavanone
• CAS-520-33-2
• SMR001233491
• LS-185786
• Flavanone, 3',5,7-trihydroxy-4'-methoxy-
• H0721
• Hesperitin; Hesperin; YSO2; Prestwick_908
• SW197026-2
• C01709
• H10029
• A828900
• Discontinued. Please see H289480 or H289501
• Flavanone, 3',5,7-trihydroxy-4'-methoxy-(VAN)
• Q411310
• SR-01000946723
• SR-01000946723-1
• BRD-K30553453-001-05-8
• BRD-K30553453-001-08-2
• Flavanone, 3',5, 7-trihydroxy-4'-methoxy- (VAN)
• Flavanone, 3',5,7-trihydroxy-4'-methoxy- (VAN) (8CI)
• Flavanone, 3',5,7-trihydroxy-4'-methoxy-(VAN) (8CI)
• (S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one;Hesperetin
• (2S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
• (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• 2,3-DIHYDRO-5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• 4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-(9CI)

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
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	12589.3 nM	Potency	via CMAUP
CHEMBL3729	P22748	Carbonic anhydrase IV	102.1 nM; 102.1 nM	Ki; Ki	PMID: 26498393; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	3.3 nM; 3.3 nM	Ki; Ki	PMID: 26498393; via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	454.1 nM; 454.1 nM	Ki; Ki	PMID: 26498393; via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	25118.9 nM	Potency	via CMAUP
CHEMBL2231	P04798	Cytochrome P450 1A1	2786 nM	IC50	PMID: 20696580
CHEMBL3356	P05177	Cytochrome P450 1A2	34647 nM	IC50	PMID: 20696580
CHEMBL4878	Q16678	Cytochrome P450 1B1	511 nM; 511 nM	IC50; IC50	PMID: 20696580; via Super-PRED
CHEMBL3622	P33261	Cytochrome P450 2C19	7943.3 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	10000 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	10000 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 10000 nM; 15848.9 nM; 10000 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL284	P27487	Dipeptidyl peptidase IV	280 nM	IC50	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	12589.3 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	26900 nM	IC50	DOI: 10.1007/s00044-012-0353-y
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	3981.1 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	5623.4 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	6309.6 nM	Potency	via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	39810.7 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP

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

• Allium fistulosum
• Artemisia dracunculus
• Artemisia xanthochroa
• Brickellia vernicosa
• Citrus × aurantium
• Citrus deliciosa
• Citrus limon
• Citrus maxima
• Citrus medica
• Citrus trifoliata
• Coriandrum sativum
• Crataegus microphylla
• Cyclopia intermedia
• Cynara cornigera
• Dalbergia parviflora
• Eriodictyon californicum
• Ficus pumila
• Isatis tinctoria
• Lactuca sativa
• Mentha arvensis
• Mentha canadensis
• Nepeta tenuifolia
• Paulownia tomentosa
• Rhododendron dauricum
• Salvia officinalis
• Solanum nigrum
• Sophora flavescens
• Spatholobus suberectus
• Syzygium jambos
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Thymus quinquecostatus
• Thymus vulgaris
• Vitis vinifera

Cross-Links

• PubChem: 72281
• NPASS: NPC302950
• ChEMBL: CHEMBL399121
• LOTUS: LTS0087195
• wikiData: Q411310