Hesperetin (Compound)

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ID	22
Name	Hesperetin
Synonyms
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000022 (Hesperetin) 3D Structure for EE000022 (Hesperetin) 72281 -OEChem-02282313063D 36 38 0 1 0 0 0 0 0999 V2000 0.5141 -0.7165 -0.0418 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4363 2.9075 -0.0960 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7353 1.6876 -0.0007 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7287 -0.1582 0.1622 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1906 -0.0387 -2.1499 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6374 -3.0583 -0.0463 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1075 0.4523 0.5151 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3568 1.7161 -0.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6096 0.2884 0.4171 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5963 0.5529 -0.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8543 1.8292 -0.0857 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8834 -0.6497 -0.0300 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2208 0.1990 -0.8331 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3808 0.2282 1.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9933 0.5452 -0.0096 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5713 -1.8637 -0.0516 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6046 0.0489 -0.9232 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6753 -0.6721 -0.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9664 -1.8737 -0.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7646 0.0782 1.4874 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3765 -0.0115 0.2371 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2364 -1.4911 0.1512 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1764 0.5071 1.5765 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1032 2.6029 0.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1261 1.7019 -1.2774 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6235 0.2332 -1.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9189 0.2969 2.5586 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0227 -2.8023 -0.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7628 -0.6887 0.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3599 0.0325 2.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6809 1.4608 0.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5032 0.0217 -2.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5934 -2.8800 -0.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8534 -2.0426 -0.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3264 -1.4419 0.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9694 -2.0104 1.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 12 1 0 0 0 0 2 11 2 0 0 0 0 3 15 1 0 0 0 0 3 31 1 0 0 0 0 4 21 1 0 0 0 0 4 22 1 0 0 0 0 5 17 1 0 0 0 0 5 32 1 0 0 0 0 6 19 1 0 0 0 0 6 33 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 7 23 1 0 0 0 0 8 11 1 0 0 0 0 8 24 1 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 13 26 1 0 0 0 0 14 20 2 0 0 0 0 14 27 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 28 1 0 0 0 0 17 21 2 0 0 0 0 18 19 2 0 0 0 0 18 29 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 22 34 1 0 0 0 0 22 35 1 0 0 0 0 22 36 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 72281 > <PUBCHEM_CONFORMER_RMSD> 0.6 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 7 12 9 5 4 15 8 6 2 13 3 10 14 11 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 30 1 -0.36 10 0.09 11 0.42 12 0.08 13 -0.15 14 -0.15 15 0.08 16 -0.15 17 0.08 18 -0.15 19 0.08 2 -0.57 20 -0.15 21 0.08 22 0.28 26 0.15 27 0.15 28 0.15 29 0.15 3 -0.53 30 0.15 31 0.45 32 0.45 33 0.45 4 -0.36 5 -0.53 6 -0.53 7 0.42 8 0.06 9 -0.14 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 2.6 > <PUBCHEM_PHARMACOPHORE_FEATURES> 9 1 1 acceptor 1 2 acceptor 1 3 donor 1 4 acceptor 1 5 donor 1 6 donor 6 1 7 8 10 11 12 rings 6 10 12 15 16 18 19 rings 6 9 13 14 17 20 21 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 22 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 1 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 63 > <PUBCHEM_CONFORMER_ID> 00011A5900000001 > <PUBCHEM_MMFF94_ENERGY> 73.6392 > <PUBCHEM_FEATURE_SELFOVERLAP> 45.702 > <PUBCHEM_SHAPE_FINGERPRINT> 10366900 7 17385446505481024283 10411042 1 18194121816423105338 11471102 20 18409169926478730480 11796584 16 16443342027874578162 12107183 9 17910968937132824129 12236239 1 17846221063984302073 12616971 3 17917710214889961797 12788726 201 17203341000464289091 13009979 54 17702673133724608786 13134695 92 18410293601487324228 13140716 1 18123469642847536848 13167823 11 18131071515358682387 13533116 47 18272370888399394179 13544653 18 18335989662196281748 13782708 43 17749390369229705499 13862211 1 18337392635181923138 13955234 65 18341610485865240312 14386348 63 17749112201113574505 15196674 1 18338237067952727936 15788980 27 18201716224112116893 15848702 151 18411421683047116253 15961568 22 16082220773320022900 17349148 13 17989488511072518439 17357779 13 18114455678328331812 17844677 252 18410017602572595909 1813 80 18200044927904478988 18186145 218 17530966852137296001 18222031 100 18341897338383513714 200 152 18343864416156517425 20028762 73 18272932678849938878 20645477 70 18334294266753059306 21033648 29 17894900850287790189 21033650 10 15864917500031889260 21065198 48 18130797732631560513 21065201 7 16443064997571703433 21267235 1 18341900654240723566 21641784 216 17969524636225772676 221357 26 18260261928641996813 22224240 67 18270956964624800488 22393880 68 17894902997781968067 22646028 1 17988923357816432195 23175994 123 18040723549883113301 23557571 272 17167857582534908229 23559900 14 16950575401388008491 2871803 45 18113902611463546650 314194 84 18272927224129968887 33824 294 18408885148888206786 345986 75 17987513719843856288 34797466 226 16732997426255352198 4073 2 18114188591977164635 42630746 31 18412828018981353920 46194498 28 17676489500969697381 465052 167 18343306950517948934 474 4 18198061580748437344 5104073 3 18272370819590383593 5281201 14 17894914018351350493 573450 72 17132114624115824881 602551 16 15195275464961939188 7970288 3 18194682570894618002 > <PUBCHEM_SHAPE_MULTIPOLES> 417.53 12.63 2.19 1.09 9.05 0.19 -0.11 5.12 -0.45 -3.78 -0.08 1.64 -0.05 -0.03 > <PUBCHEM_SHAPE_SELFOVERLAP> 920.917 > <PUBCHEM_SHAPE_VOLUME> 224.4 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4'-O-methylated flavonoids
CAS number	520-33-2
PubChem ID	72281
ChEBI ID	28230
FooDB ID	FDB002677
HMDB ID	HMDB0005782

Chemical data

MolDBi data

IUPAC Name	(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional IUPAC Name	hesperetin
Formula	C16H14O6
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
Molecular weight	302.2788
Exact mass	302.07903818
SMILES	COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.
Kingdom	Organic compounds
Super Class	Phenylpropanoids and polyketides
Class	Flavonoids
Sub Class	O-methylated flavonoids
Direct Parent	4'-O-methylated flavonoids
Alternative Parents	3'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavanones Chromones Methoxyphenols Methoxybenzenes Aryl alkyl ketones Anisoles Phenoxy compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids Vinylogous acids Oxacyclic compounds Hydrocarbon derivatives Organic oxides

Publications with Hesperetin

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of Hesperetin in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of Hesperetin with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of Hesperetin with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of Hesperetin exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of Hesperetin exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication