Arachidonic acid (AA; cis-20:4n-6) (Compound)

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ID	224
Name	Arachidonic acid (AA; cis-20:4n-6)
Synonyms	all-cis-5,8,11,14-Eicosatetraenoic acid; Arachidonate
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000224 (Arachidonic acid (AA; cis-20:4n-6)) 3D Structure for EE000224 (Arachidonic acid (AA; cis-20:4n-6)) 444899 -OEChem-03032322173D 54 53 0 0 0 0 0 0 0999 V2000 -0.0983 -2.0287 2.9613 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3550 -0.4083 1.9797 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0825 1.8540 -0.9263 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4134 1.6686 -0.1912 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1636 2.8901 -0.2710 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3014 0.6476 -0.9039 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1704 3.0180 -0.9490 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 0.4809 -0.1964 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5028 -2.5433 -0.1502 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0307 -2.6532 -0.5605 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3387 2.7406 -0.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4605 2.2683 1.0684 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7171 -2.7122 1.3518 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3118 -2.6193 -2.0257 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7108 -0.5419 -2.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8983 2.1310 1.4749 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0633 -1.7173 -2.6757 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0080 -0.3011 0.8746 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5889 0.9839 1.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1302 -0.8386 -1.6146 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6824 -0.7298 -0.3962 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0617 -1.5890 2.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2787 2.1518 -1.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5618 0.8889 -0.9704 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2253 1.3420 0.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9336 2.6323 -0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6530 3.8715 -0.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0663 2.6492 0.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7969 -0.3228 -0.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4818 0.9686 -1.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1766 3.3545 -1.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1847 1.4280 -0.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2561 -0.2518 -0.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4946 0.1297 0.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8891 -1.5723 -0.4777 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0834 -3.3101 -0.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3496 -3.6131 -0.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5408 -1.8979 -0.0178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2453 2.8632 -0.9400 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8848 1.3540 1.2320 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0220 3.0214 1.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3182 -3.6753 1.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7850 -2.7028 1.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1026 -3.4353 -2.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7234 0.2868 -2.7208 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1037 -0.1778 -1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2305 -1.8421 -3.7425 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4039 3.0190 1.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2002 -1.0751 1.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9260 -0.2852 0.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6292 0.9775 1.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7851 -1.1563 -2.4252 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7379 -0.9845 -0.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3292 -1.2895 3.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 1 54 1 0 0 0 0 2 22 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 3 23 1 0 0 0 0 3 24 1 0 0 0 0 4 6 1 0 0 0 0 4 25 1 0 0 0 0 4 26 1 0 0 0 0 5 7 1 0 0 0 0 5 27 1 0 0 0 0 5 28 1 0 0 0 0 6 8 1 0 0 0 0 6 29 1 0 0 0 0 6 30 1 0 0 0 0 7 11 2 0 0 0 0 7 31 1 0 0 0 0 8 32 1 0 0 0 0 8 33 1 0 0 0 0 8 34 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 9 35 1 0 0 0 0 9 36 1 0 0 0 0 10 14 1 0 0 0 0 10 37 1 0 0 0 0 10 38 1 0 0 0 0 11 12 1 0 0 0 0 11 39 1 0 0 0 0 12 16 1 0 0 0 0 12 40 1 0 0 0 0 12 41 1 0 0 0 0 13 22 1 0 0 0 0 13 42 1 0 0 0 0 13 43 1 0 0 0 0 14 17 2 0 0 0 0 14 44 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 15 45 1 0 0 0 0 15 46 1 0 0 0 0 16 19 2 0 0 0 0 16 48 1 0 0 0 0 17 47 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 18 49 1 0 0 0 0 18 50 1 0 0 0 0 19 51 1 0 0 0 0 20 21 2 0 0 0 0 20 52 1 0 0 0 0 21 53 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 444899 > <PUBCHEM_CONFORMER_RMSD> 1.4 > <PUBCHEM_CONFORMER_DIVERSEORDER> 5 54 102 35 154 142 6 147 61 3 58 47 75 92 8 126 114 135 56 57 111 94 117 50 144 122 99 49 97 98 106 67 91 151 1 79 63 25 95 36 145 84 59 143 146 82 123 155 4 42 131 128 44 64 121 17 65 26 21 153 83 28 156 152 139 46 34 45 70 96 133 24 90 55 76 60 118 74 51 129 31 110 148 136 137 100 38 138 113 105 9 15 80 88 66 48 23 150 52 33 120 125 29 62 20 11 32 27 18 109 140 22 112 127 7 85 78 68 71 10 124 119 40 93 13 77 101 69 115 116 30 72 37 130 134 2 108 14 107 16 86 104 141 12 19 87 39 73 41 43 53 132 89 149 103 81 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 26 1 -0.65 10 0.14 11 -0.29 12 0.28 13 0.06 14 -0.29 15 0.28 16 -0.29 17 -0.29 18 0.28 19 -0.29 2 -0.57 20 -0.29 21 -0.29 22 0.66 31 0.15 39 0.15 44 0.15 47 0.15 48 0.15 5 0.14 51 0.15 52 0.15 53 0.15 54 0.5 7 -0.29 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 14 > <PUBCHEM_PHARMACOPHORE_FEATURES> 6 1 1 acceptor 1 2 acceptor 1 8 hydrophobe 3 1 2 22 anion 4 9 10 13 14 hydrophobe 5 3 4 5 6 7 hydrophobe > <PUBCHEM_HEAVY_ATOM_COUNT> 22 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 4 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 1 > <PUBCHEM_CONFORMER_ID> 0006C9E300000005 > <PUBCHEM_MMFF94_ENERGY> 11.2385 > <PUBCHEM_FEATURE_SELFOVERLAP> 30.505 > <PUBCHEM_SHAPE_FINGERPRINT> 10816530 23 17556275595369305321 12422481 6 18122086435966686627 13402501 40 18343021056114518020 13965767 371 17336487687605168096 14251757 17 18059294266963737415 14251764 3 18410295783245918235 14251764 38 18196646513767737519 15406563 5 7996814547659378681 20905425 154 17831285117190428593 238 59 17846787264985412230 35225 105 17894901910891134430 4409770 3 17981074954251392990 > <PUBCHEM_SHAPE_MULTIPOLES> 441.01 7 4.36 2.59 6.47 0.39 -0.67 2.54 0.2 0.25 0.38 -0.87 -1.89 2.25 > <PUBCHEM_SHAPE_SELFOVERLAP> 829.998 > <PUBCHEM_SHAPE_VOLUME> 271.6 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Long-chain fatty acids
CAS number	506-32-1
PubChem ID	444899
ChEBI ID	15843
FooDB ID	FDB011872
HMDB ID	HMDB0001043

Chemical data

MolDBi data

IUPAC Name	(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid
Traditional IUPAC Name	arachidonic acid
Formula	C20H32O2
InChI	InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
InChI Key	YZXBAPSDXZZRGB-DOFZRALJSA-N
Molecular weight	304.4669
Exact mass	304.240230268
SMILES	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acids and conjugates
Direct Parent	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 Arachidonic acid (AA; cis-20:4n-6)

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 Arachidonic acid (AA; cis-20:4n-6) 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 Arachidonic acid (AA; cis-20:4n-6) 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 Arachidonic acid (AA; cis-20:4n-6) 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 Arachidonic acid (AA; cis-20:4n-6) 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 Arachidonic acid (AA; cis-20:4n-6) 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