Enterolactone (Compound)

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ID	31
Name	Enterolactone
Synonyms	(-)-Enterolactone
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000031 (Enterolactone) 3D Structure for EE000031 (Enterolactone) 123917 -OEChem-10221915523D 40 42 0 1 0 0 0 0 0999 V2000 -4.0582 0.4473 0.3979 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9188 -0.5225 -1.6735 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5849 1.6916 -2.4229 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7863 -2.0505 2.1079 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7745 0.6408 0.8923 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9341 -0.3120 -0.2877 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1641 0.6500 1.4976 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3722 2.0418 0.4231 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6485 -1.7624 0.0757 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3923 -0.1513 -0.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1163 2.1612 0.2196 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1793 -2.0860 -0.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6605 1.8673 -1.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9186 2.5627 1.2775 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6256 -1.9150 1.1028 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3446 -2.5494 -1.2114 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0382 1.9776 -1.2098 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2962 2.6730 1.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9854 -2.2144 1.0198 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7044 -2.8488 -1.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8561 2.3804 -0.1542 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5248 -2.6814 -0.1788 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0558 0.3007 1.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3541 -0.0073 -1.1618 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3083 -0.1732 2.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4162 1.5866 2.0036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6705 2.7896 1.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9009 2.3312 -0.4948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1944 -2.4388 -0.5967 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0237 -2.0091 1.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0262 1.5738 -1.8530 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4932 2.7898 2.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2054 -1.5648 2.0414 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2852 -2.6803 -2.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9332 2.9853 1.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1247 -3.2110 -2.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9301 2.4674 -0.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5835 -2.9154 -0.2500 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8764 1.4242 -3.0333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2498 -1.7159 2.8470 H 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 10 1 0 0 0 0 2 10 2 0 0 0 0 3 17 1 0 0 0 0 3 39 1 0 0 0 0 4 19 1 0 0 0 0 4 40 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 5 23 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 7 26 1 0 0 0 0 8 11 1 0 0 0 0 8 27 1 0 0 0 0 8 28 1 0 0 0 0 9 12 1 0 0 0 0 9 29 1 0 0 0 0 9 30 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 31 1 0 0 0 0 14 18 2 0 0 0 0 14 32 1 0 0 0 0 15 19 1 0 0 0 0 15 33 1 0 0 0 0 16 20 2 0 0 0 0 16 34 1 0 0 0 0 17 21 2 0 0 0 0 18 21 1 0 0 0 0 18 35 1 0 0 0 0 19 22 2 0 0 0 0 20 22 1 0 0 0 0 20 36 1 0 0 0 0 21 37 1 0 0 0 0 22 38 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 123917 > <PUBCHEM_CONFORMER_RMSD> 0.8 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 19 218 76 192 291 228 214 188 279 100 163 268 222 55 109 253 259 225 285 249 275 271 251 293 244 260 138 240 200 198 157 236 129 28 277 97 224 41 21 269 139 194 179 296 105 289 219 288 130 226 223 160 212 196 274 186 261 153 101 6 263 199 29 94 278 258 254 111 294 297 184 85 193 257 276 220 181 264 154 64 221 106 158 170 4 99 227 143 31 262 75 207 280 77 73 10 210 197 128 216 162 159 237 15 209 206 189 231 103 281 155 98 302 230 180 13 245 234 201 42 161 229 5 95 282 238 16 56 301 126 51 191 248 265 203 290 256 146 113 48 22 190 18 250 284 132 17 266 156 96 168 171 3 246 49 185 149 36 86 127 11 164 283 30 178 2 117 68 71 47 9 202 119 195 102 252 267 12 247 20 104 44 243 54 211 88 205 133 52 141 69 172 60 235 43 148 175 110 27 122 79 37 287 25 173 78 120 140 145 91 108 131 124 59 107 82 26 53 187 45 7 46 74 112 80 40 177 152 116 174 57 81 50 121 123 182 65 34 255 167 66 125 14 33 183 166 295 70 115 176 169 32 35 233 151 150 118 165 204 72 83 217 24 292 298 8 23 136 38 299 273 89 135 58 114 90 286 147 232 67 242 39 215 134 208 63 87 213 62 142 84 92 239 137 300 61 93 241 144 272 270 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 31 1 -0.43 10 0.66 11 -0.14 12 -0.14 13 -0.15 14 -0.15 15 -0.15 16 -0.15 17 0.08 18 -0.15 19 0.08 2 -0.57 20 -0.15 21 -0.15 22 -0.15 3 -0.53 31 0.15 32 0.15 33 0.15 34 0.15 35 0.15 36 0.15 37 0.15 38 0.15 39 0.45 4 -0.53 40 0.45 6 0.06 7 0.28 8 0.14 9 0.14 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 4.8 > <PUBCHEM_PHARMACOPHORE_FEATURES> 6 1 2 acceptor 1 3 donor 1 4 donor 5 1 5 6 7 10 rings 6 11 13 14 17 18 21 rings 6 12 15 16 19 20 22 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 22 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 2 > <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> 160 > <PUBCHEM_CONFORMER_ID> 0001E40D00000001 > <PUBCHEM_MMFF94_ENERGY> 53.3037 > <PUBCHEM_FEATURE_SELFOVERLAP> 30.447 > <PUBCHEM_SHAPE_FINGERPRINT> 107951 10 17462593889484423646 10989021 7 18339924788684596243 11578080 2 17458352931481311871 12035759 4 17770484641505650567 12156800 1 15190742320713384382 12592029 89 18115866489670550619 133893 2 18260269633570414177 13681431 1 18263646173343699991 14181834 199 18336529565249652287 14840074 17 18115567349826083624 14955137 171 17839488604095404371 15463212 79 17465662699157234452 16752209 62 17543057335167198155 17357779 13 17908678662785569695 17492 54 18189071840751493390 18769570 83 17248619791207912733 19591789 44 17187839260950446687 20600515 1 17971752172951232298 20645476 183 17245265563130222796 20905425 154 18339654381369128645 21421861 104 18197514947196386737 23419403 2 17756101714705558540 23557571 272 17691965964512408922 35225 105 17396425378103027222 5845 1 17908696233391223775 6287921 2 17917143880128167474 6443956 14 18196645199123129417 7364860 26 18342461421812415449 81228 2 17400649216424324747 9925002 15 17842523444555256135 > <PUBCHEM_SHAPE_MULTIPOLES> 429.27 5.33 4.43 1.75 4.24 0.79 -0.2 -0.68 -0.42 -4.28 0.12 -0.78 0.02 -1.05 > <PUBCHEM_SHAPE_SELFOVERLAP> 930.813 > <PUBCHEM_SHAPE_VOLUME> 235.4 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	Mostly measured after enzymatic hydrolysis.
Classification	Compounds > Chemical entities > Organic compounds > Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9'-epoxylignans > Dibenzylbutyrolactone lignans
CAS number	78473-71-9
PubChem ID	10685477
ChEBI ID	81555
FooDB ID	FDB002488
HMDB ID	HMDB0006101

Chemical data

MolDBi data

IUPAC Name	3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
Traditional IUPAC Name	HPMF
Formula	C18H18O4
InChI	InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1
InChI Key	HVDGDHBAMCBBLR-WMLDXEAASA-N
Molecular weight	298.3331
Exact mass	298.120509064
SMILES	OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC=C2)=C1

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
Kingdom	Organic compounds
Super Class	Lignans, neolignans and related compounds
Class	Furanoid lignans
Sub Class	Tetrahydrofuran lignans
Direct Parent	Dibenzylbutyrolactone lignans
Alternative Parents	Lignan lactones 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Gamma butyrolactones Benzene and substituted derivatives Tetrahydrofurans Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds

Publications with Enterolactone

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 Enterolactone 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 Enterolactone 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 Enterolactone 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 Enterolactone 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 Enterolactone 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