alpha-Linolenic acid (ALA; cis-18:3n-3) (Compound)

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ID	182
Name	alpha-Linolenic acid (ALA; cis-18:3n-3)
Synonyms	all-cis-9,12,15-Octadecatrienoic acid
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE000182 (alpha-Linolenic acid (ALA; cis-18:3n-3)) 3D Structure for EE000182 (alpha-Linolenic acid (ALA; cis-18:3n-3)) 5280934 -OEChem-02282312423D 50 49 0 0 0 0 0 0 0999 V2000 4.1813 -0.9790 -0.6113 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5798 0.2316 1.2706 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7602 2.7874 0.0367 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6525 2.2005 0.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8161 1.7643 -0.3899 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6977 3.2044 0.6150 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2191 2.3801 -0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0946 2.5857 0.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2931 1.3937 -0.8275 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7513 2.0080 -0.4639 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3720 0.1808 0.0653 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1060 0.7309 -0.6733 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8919 -0.3667 0.3290 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7767 -1.7053 -0.3402 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6093 -2.2665 -0.6898 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2726 -1.6257 -0.4552 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7328 -1.9587 0.9051 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -3.0132 1.1573 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.9923 0.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8070 -3.5600 -0.5356 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7628 3.6297 -0.6660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0301 3.1935 1.0196 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9361 1.8337 -0.8789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6404 1.3377 0.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5812 1.3932 -1.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7752 0.9052 0.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3856 3.6064 1.5865 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7465 4.0517 -0.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4498 2.7376 0.6324 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2423 3.2537 -1.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7629 3.3764 1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0600 1.8538 1.5753 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0941 1.0742 -1.8573 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2789 1.8717 -0.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9699 2.7230 -1.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6128 0.4880 -1.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0308 -0.1790 0.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7651 -0.4072 0.9923 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6986 -2.2385 -0.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6221 -3.2438 -1.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5919 -1.9363 -1.2555 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3259 -0.5390 -0.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2427 -1.7592 -0.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0027 -1.3038 1.7293 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4134 -3.1702 2.1718 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2640 -4.1449 -0.6585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6372 -4.9697 0.5886 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7112 -2.5924 -1.0384 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1197 -4.2974 -1.2819 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6045 -3.4797 0.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 1 43 1 0 0 0 0 2 11 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 3 21 1 0 0 0 0 3 22 1 0 0 0 0 4 6 1 0 0 0 0 4 23 1 0 0 0 0 4 24 1 0 0 0 0 5 7 1 0 0 0 0 5 25 1 0 0 0 0 5 26 1 0 0 0 0 6 8 1 0 0 0 0 6 27 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 7 29 1 0 0 0 0 7 30 1 0 0 0 0 8 10 1 0 0 0 0 8 31 1 0 0 0 0 8 32 1 0 0 0 0 9 11 1 0 0 0 0 9 33 1 0 0 0 0 9 34 1 0 0 0 0 10 12 2 0 0 0 0 10 35 1 0 0 0 0 12 13 1 0 0 0 0 12 36 1 0 0 0 0 13 14 1 0 0 0 0 13 37 1 0 0 0 0 13 38 1 0 0 0 0 14 15 2 0 0 0 0 14 39 1 0 0 0 0 15 16 1 0 0 0 0 15 40 1 0 0 0 0 16 17 1 0 0 0 0 16 41 1 0 0 0 0 16 42 1 0 0 0 0 17 18 2 0 0 0 0 17 44 1 0 0 0 0 18 19 1 0 0 0 0 18 45 1 0 0 0 0 19 20 1 0 0 0 0 19 46 1 0 0 0 0 19 47 1 0 0 0 0 20 48 1 0 0 0 0 20 49 1 0 0 0 0 20 50 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 5280934 > <PUBCHEM_CONFORMER_RMSD> 1.4 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 4 51 55 19 56 35 72 15 67 20 11 78 69 46 83 27 8 21 34 10 71 32 77 33 64 28 7 42 14 17 47 76 6 29 48 59 66 62 60 73 30 63 16 75 61 54 68 24 3 36 13 58 25 70 86 23 38 37 52 87 84 74 50 82 9 44 22 65 57 49 26 85 18 12 39 5 79 43 81 31 40 2 45 41 53 80 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 21 1 -0.65 10 -0.29 11 0.66 12 -0.29 13 0.28 14 -0.29 15 -0.29 16 0.28 17 -0.29 18 -0.29 19 0.14 2 -0.57 35 0.15 36 0.15 39 0.15 40 0.15 43 0.5 44 0.15 45 0.15 8 0.14 9 0.06 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 13 > <PUBCHEM_PHARMACOPHORE_FEATURES> 4 1 1 acceptor 1 2 acceptor 1 20 hydrophobe 3 1 2 11 anion > <PUBCHEM_HEAVY_ATOM_COUNT> 20 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 0 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 3 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 1 > <PUBCHEM_CONFORMER_ID> 005094A600000001 > <PUBCHEM_MMFF94_ENERGY> 10.2711 > <PUBCHEM_FEATURE_SELFOVERLAP> 20.355 > <PUBCHEM_SHAPE_FINGERPRINT> 10693767 8 17482251014438567359 12038231 1 18266462001305944430 12788726 201 18340777051825042064 14117953 113 16609410889143086117 14251740 79 18341624736382072696 14251751 93 18409444795621595145 14251757 17 18059025977162098966 14251757 5 18120105136802325084 14916288 52 17329714735033680357 15006816 218 18338237063620467077 15322534 239 18410020909628868326 16120349 306 18337099077945037024 16719943 64 18336827593320485018 17093844 170 18411979148907614250 17859628 97 18409450302154965905 20775438 99 16257538104570400991 23559900 14 18271239546970486808 3027735 51 18413111670968322651 3084891 72 18339360880531546139 338550 245 18335427811965491524 5282940 2 18264769861706440569 5309563 4 16462492603747227850 6287921 2 17623284970746165187 9543594 6 18124313809868569158 > <PUBCHEM_SHAPE_MULTIPOLES> 399.85 9.08 5.65 0.99 5.34 2.85 -0.14 -3.27 1.1 -0.39 -0.46 0.12 0.18 -0.61 > <PUBCHEM_SHAPE_SELFOVERLAP> 749.198 > <PUBCHEM_SHAPE_VOLUME> 247 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives
CAS number	463-40-1
PubChem ID	5280934
ChEBI ID	27432
FooDB ID	FDB012462
HMDB ID	HMDB0001388

Chemical data

MolDBi data

IUPAC Name	(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional IUPAC Name	α linolenic acid
Formula	C18H30O2
InChI	InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
InChI Key	DTOSIQBPPRVQHS-PDBXOOCHSA-N
Molecular weight	278.4296
Exact mass	278.224580204
SMILES	CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Lineolic acids and derivatives
Direct Parent	Lineolic acids and derivatives
Alternative Parents	Long-chain fatty acids Unsaturated fatty acids Straight chain fatty acids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds

Publications with alpha-Linolenic acid (ALA; cis-18:3n-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 alpha-Linolenic acid (ALA; cis-18:3n-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 alpha-Linolenic acid (ALA; cis-18:3n-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 alpha-Linolenic acid (ALA; cis-18:3n-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 alpha-Linolenic acid (ALA; cis-18:3n-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 alpha-Linolenic acid (ALA; cis-18:3n-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