Apigenin (Compound)

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ID	46
Name	Apigenin
Synonyms
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000046 (Apigenin) 3D Structure for EE000046 (Apigenin) 5280443 -OEChem-09032120193D 30 32 0 0 0 0 0 0 0999 V2000 -0.0681 0.7800 -0.0476 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1237 -1.8702 0.1093 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7265 -2.9343 0.1829 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3310 2.8645 -0.1990 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2534 0.6490 -0.0391 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0651 -0.6003 0.0351 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 0.6394 -0.0429 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7138 -0.3621 0.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1664 -0.0973 0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2389 -1.8145 0.1154 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2238 -1.6099 0.1094 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4593 -0.6835 0.0353 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1933 1.8062 -0.1218 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5862 1.7275 -0.1217 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2176 0.4853 -0.0433 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0430 -1.0335 -0.5363 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6702 1.0909 0.5521 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4151 -0.7831 -0.5550 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0423 1.3414 0.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9148 0.4043 -0.0203 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8368 -2.5001 0.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7039 2.7750 -0.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3033 0.4227 -0.0434 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6918 -1.9600 -0.9827 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0141 1.8350 0.9973 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0842 -1.5187 -0.9936 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4259 2.2675 0.9526 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4973 -2.6081 0.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2737 2.6256 -0.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7054 -0.1037 -0.4576 H 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 8 1 0 0 0 0 2 12 1 0 0 0 0 2 28 1 0 0 0 0 3 10 2 0 0 0 0 4 14 1 0 0 0 0 4 29 1 0 0 0 0 5 20 1 0 0 0 0 5 30 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 5280443 > <PUBCHEM_CONFORMER_RMSD> 0.6 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 30 1 -0.16 10 0.47 11 -0.14 12 0.08 13 -0.15 14 0.08 15 -0.15 16 -0.15 17 -0.15 18 -0.15 19 -0.15 2 -0.53 20 0.08 21 0.15 22 0.15 23 0.15 24 0.15 25 0.15 26 0.15 27 0.15 28 0.45 29 0.45 3 -0.57 30 0.45 4 -0.53 5 -0.53 6 0.09 7 0.08 8 0.05 9 0.03 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 1 > <PUBCHEM_PHARMACOPHORE_FEATURES> 8 1 1 acceptor 1 2 donor 1 3 acceptor 1 4 donor 1 5 donor 6 1 6 7 8 10 11 rings 6 6 7 12 13 14 15 rings 6 9 16 17 18 19 20 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 20 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <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> 57 > <PUBCHEM_CONFORMER_ID> 005092BB00000001 > <PUBCHEM_MMFF94_ENERGY> 60.7436 > <PUBCHEM_FEATURE_SELFOVERLAP> 40.625 > <PUBCHEM_SHAPE_FINGERPRINT> 10014705 185 18335983090743610973 10319926 262 18339344337187947850 10411042 1 17833271196427205891 10493431 412 18339369544277550625 10498660 4 18336260146151624709 10608611 8 18342173405853837512 10646746 165 18410292501880224548 11315181 36 17967532415338923724 12107183 9 17973996255225508682 12173636 292 18409726227717107541 12236239 1 17458341966376888130 12390115 104 18270696268119625369 12403259 415 18202279234227041088 12500047 106 18411979165633848254 13073987 5 18334573538601782738 13140716 1 17974859676764465403 13544592 145 18269848531875060550 14508225 48 18124582335750861655 14790565 3 17908712730609502257 15042514 8 18192436496683379403 15196674 1 18411138009184468990 15375358 24 18272089392275024390 17844677 252 18338524131077601056 18186145 218 18201727210401115800 200 152 17060622204808618226 20510252 161 18342459253144016673 20645477 56 18410013234284757832 20645477 70 17203058396143606462 21033648 29 18271516554985427096 21065198 57 18411699920035301594 21236236 1 18412826893710328947 21267235 1 18337116777299593123 21279426 13 18269277859449011198 21421861 104 17750502976618702298 23402539 116 18412538829647092654 23402655 69 18131067100338114972 23557571 272 18342746247148492668 23559900 14 18271807861775124550 245318 6 16448986100328701468 283562 15 18410291424461079675 2916195 48 18342730849902058064 3004659 81 18335425613612532158 335352 9 18267022748231475478 350125 39 18410298038462750009 3545911 37 18342460348455732712 4028521 119 18341892965631935697 4214541 1 18411419514231212472 474 4 16879077545412114420 495365 180 17346021334593014002 5104073 3 18410011005465809410 542803 24 17530686524359763644 559249 180 18337386046670377618 633830 44 18199743644401676445 69090 78 18272086119177836790 77779 3 18412263930592437412 9709674 26 18342463655380539086 > <PUBCHEM_SHAPE_MULTIPOLES> 382.24 10.96 2.41 0.66 9.09 0.24 0 -3.75 0.48 -2.84 -0.06 0.21 -0.01 0.71 > <PUBCHEM_SHAPE_SELFOVERLAP> 856.39 > <PUBCHEM_SHAPE_VOLUME> 201.3 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Phenylpropanoids and polyketides > Flavonoids > Flavones
CAS number	520-36-5
PubChem ID	5280443
ChEBI ID	18388
FooDB ID	FDB002798
HMDB ID	HMDB0002124

Chemical data

MolDBi data

IUPAC Name	5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional IUPAC Name	chamomile
Formula	C15H10O5
InChI	InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
InChI Key	KZNIFHPLKGYRTM-UHFFFAOYSA-N
Molecular weight	270.2369
Exact mass	270.05282343
SMILES	OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
Kingdom	Organic compounds
Super Class	Phenylpropanoids and polyketides
Class	Flavonoids
Sub Class	Flavones
Direct Parent	Flavones
Alternative Parents	7-hydroxyflavonoids 5-hydroxyflavonoids 4'-hydroxyflavonoids Chromones Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives

Publications with Apigenin

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 Apigenin 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 Apigenin 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 Apigenin 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 Apigenin 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 Apigenin 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