DHA (cis-22:6n-3) (Compound)

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ID	184
Name	DHA (cis-22:6n-3)
Synonyms	all-cis-4,7,10,13,16,19-Docosahexaenoic acid; Docosahexaenoate; Docosahexaenoic acid
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000184 (DHA (cis-22:6n-3)) 3D Structure for EE000184 (DHA (cis-22:6n-3)) 445580 -OEChem-03112023463D 56 55 0 0 0 0 0 0 0999 V2000 -3.3950 -1.4509 1.3010 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6390 -2.6325 -0.1892 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7398 -0.4666 -1.7205 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4045 1.6390 -1.8489 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3045 2.0927 0.9781 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0375 0.8212 2.3842 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9313 -0.3955 -0.7693 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6563 0.7361 -2.6177 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5361 -1.9697 0.9573 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6605 1.6347 -2.6709 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2252 2.9370 -1.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6272 3.1408 0.1452 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0073 2.2749 2.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3566 -1.2961 -1.5586 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0361 1.7077 3.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0833 -0.5459 3.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8719 -1.7274 2.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5575 -2.8527 0.2988 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3205 -2.5714 -0.7689 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7293 -1.0331 -2.1069 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4815 0.2468 -0.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6771 -0.3455 -1.4529 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0409 -1.6102 0.1192 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9441 1.6667 -0.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8259 -0.6269 -1.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8406 -1.3560 -2.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4423 1.5382 -2.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3098 0.7764 -1.1905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3881 2.2227 0.8587 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1040 1.0647 0.6731 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0249 1.2766 2.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9208 0.7810 1.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8726 -0.3089 -1.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8763 0.4970 -0.1349 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4939 0.8763 -3.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4304 -2.4877 0.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3906 -1.0423 0.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7571 2.4382 -3.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2285 3.7618 -1.6624 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4968 4.1336 0.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6699 2.9204 3.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9966 -0.4449 -0.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6709 -1.3921 -2.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1799 1.9131 4.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3264 -0.5740 4.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9411 -2.6167 3.0252 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6570 -3.8513 0.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9623 -3.3763 -1.1272 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9611 -1.4350 -3.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8204 -0.3651 0.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4497 0.2543 0.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6408 -0.1943 -1.9316 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9561 1.7006 -0.6418 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6162 2.3108 -0.7493 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8525 2.0933 0.8320 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4663 -2.2480 1.8683 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 1 56 1 0 0 0 0 2 23 2 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 3 25 1 0 0 0 0 3 26 1 0 0 0 0 4 10 1 0 0 0 0 4 11 1 0 0 0 0 4 27 1 0 0 0 0 4 28 1 0 0 0 0 5 12 1 0 0 0 0 5 13 1 0 0 0 0 5 29 1 0 0 0 0 5 30 1 0 0 0 0 6 15 1 0 0 0 0 6 16 1 0 0 0 0 6 31 1 0 0 0 0 6 32 1 0 0 0 0 7 23 1 0 0 0 0 7 33 1 0 0 0 0 7 34 1 0 0 0 0 8 10 2 0 0 0 0 8 35 1 0 0 0 0 9 17 1 0 0 0 0 9 18 1 0 0 0 0 9 36 1 0 0 0 0 9 37 1 0 0 0 0 10 38 1 0 0 0 0 11 12 2 0 0 0 0 11 39 1 0 0 0 0 12 40 1 0 0 0 0 13 15 2 0 0 0 0 13 41 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 14 42 1 0 0 0 0 14 43 1 0 0 0 0 15 44 1 0 0 0 0 16 17 2 0 0 0 0 16 45 1 0 0 0 0 17 46 1 0 0 0 0 18 19 2 0 0 0 0 18 47 1 0 0 0 0 19 48 1 0 0 0 0 20 22 2 0 0 0 0 20 49 1 0 0 0 0 21 22 1 0 0 0 0 21 24 1 0 0 0 0 21 50 1 0 0 0 0 21 51 1 0 0 0 0 22 52 1 0 0 0 0 24 53 1 0 0 0 0 24 54 1 0 0 0 0 24 55 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 445580 > <PUBCHEM_CONFORMER_RMSD> 1.4 > <PUBCHEM_CONFORMER_DIVERSEORDER> 5 109 98 141 212 8 148 118 80 171 194 71 206 169 33 184 35 207 107 166 180 6 133 205 95 25 134 11 156 86 29 190 152 93 178 69 41 161 9 143 48 126 155 120 203 154 145 2 209 12 73 151 3 89 121 113 105 102 186 210 14 201 56 58 211 32 38 63 193 79 20 198 165 28 123 204 1 176 202 97 36 137 157 187 177 100 191 94 130 54 70 189 122 22 146 167 81 144 37 192 17 170 117 34 142 149 159 68 131 110 39 108 199 13 85 163 168 78 179 136 99 42 16 195 66 147 77 174 23 114 129 138 90 200 64 21 4 83 49 182 30 19 59 27 115 46 150 196 55 181 84 135 101 153 26 116 160 74 111 47 40 106 76 91 197 18 87 128 125 82 62 112 185 172 51 104 61 164 175 43 92 24 119 158 45 188 183 88 162 127 44 57 65 124 173 208 72 53 96 15 50 103 52 10 75 60 140 132 67 7 31 139 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 36 1 -0.65 10 -0.29 11 -0.29 12 -0.29 13 -0.29 14 0.28 15 -0.29 16 -0.29 17 -0.29 18 -0.29 19 -0.29 2 -0.57 20 -0.29 21 0.14 22 -0.29 23 0.66 3 0.14 35 0.15 38 0.15 39 0.15 4 0.28 40 0.15 41 0.15 44 0.15 45 0.15 46 0.15 47 0.15 48 0.15 49 0.15 5 0.28 52 0.15 56 0.5 6 0.28 7 0.06 8 -0.29 9 0.28 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 14 > <PUBCHEM_PHARMACOPHORE_FEATURES> 4 1 1 acceptor 1 2 acceptor 1 24 hydrophobe 3 1 2 23 anion > <PUBCHEM_HEAVY_ATOM_COUNT> 24 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 6 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 1 > <PUBCHEM_CONFORMER_ID> 0006CC8C00000005 > <PUBCHEM_MMFF94_ENERGY> 15.9924 > <PUBCHEM_FEATURE_SELFOVERLAP> 20.355 > <PUBCHEM_SHAPE_FINGERPRINT> 12156800 1 14059822069363593729 13773456 73 10591183842900669693 14251757 17 18188208822454229948 14932701 244 17775567516583551432 15664445 248 18125687211329475572 18981168 100 14926498559346925120 20397935 3 17461125860898610163 20429585 67 18412268358344932499 23419403 2 17174940769357966347 35225 105 17341252563389558117 469060 322 17823158802832431892 4742675 86 17970376791822041406 > <PUBCHEM_SHAPE_MULTIPOLES> 482.17 7.62 3.78 3.63 1.34 0.56 1.09 -4.59 -3.99 -1.08 0.83 -0.32 1.2 0.71 > <PUBCHEM_SHAPE_SELFOVERLAP> 918.335 > <PUBCHEM_SHAPE_VOLUME> 292.2 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Very long-chain fatty acids
CAS number	6217-54-5
PubChem ID	445580
ChEBI ID	28125
FooDB ID	FDB003003
HMDB ID	HMDB0002183

Chemical data

MolDBi data

IUPAC Name	(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
Traditional IUPAC Name	docosahexaenoic acid
Formula	C22H32O2
InChI	InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI Key	MBMBGCFOFBJSGT-KUBAVDMBSA-N
Molecular weight	328.4883
Exact mass	328.240230268
SMILES	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	Very long-chain fatty acids
Alternative Parents	Unsaturated fatty acids Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds

Publications with DHA (cis-22:6n-3)

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 DHA (cis-22:6n-3) 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 DHA (cis-22:6n-3) 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 DHA (cis-22:6n-3) 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 DHA (cis-22:6n-3) 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 DHA (cis-22:6n-3) 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