Np mrd loader

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:00 UTC
NP-MRD IDNP0000694
Secondary Accession NumbersNone
Natural Product Identification
Common NameAlpha-Linolenic acid
DescriptionAlpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. Alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. Alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). Alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
(9,12,15)-Linolenic acidChEBI
(9Z,12Z,15Z)-Octadecatrienoic acidChEBI
(Z,Z,Z)-9,12,15-Octadecatrienoic acidChEBI
9,12,15-Octadecatrienoic acidChEBI
9-cis,12-cis,15-cis-Octadecatrienoic acidChEBI
ALAChEBI
all-cis-9,12,15-Octadecatrienoic acidChEBI
cis,cis,cis-9,12,15-Octadecatrienoic acidChEBI
cis-Delta(9,12,15)-Octadecatrienoic acidChEBI
Linolenic acidChEBI
LinolenateKegg
alpha-LinolenateKegg
(9,12,15)-LinolenateGenerator
(9Z,12Z,15Z)-OctadecatrienoateGenerator
(Z,Z,Z)-9,12,15-OctadecatrienoateGenerator
9,12,15-OctadecatrienoateGenerator
9-cis,12-cis,15-cis-OctadecatrienoateGenerator
all-cis-9,12,15-OctadecatrienoateGenerator
cis,cis,cis-9,12,15-OctadecatrienoateGenerator
cis-delta(9,12,15)-OctadecatrienoateGenerator
cis-Δ(9,12,15)-octadecatrienoateGenerator
cis-Δ(9,12,15)-octadecatrienoic acidGenerator
a-LinolenateGenerator
a-Linolenic acidGenerator
Α-linolenateGenerator
Α-linolenic acidGenerator
alpha Linolenic acidHMDB
cis-9,12,15-OctadecatrienoateHMDB
cis-9,12,15-Octadecatrienoic acidHMDB
Industrene 120HMDB
FA(18:3(9Z,12Z,15Z))HMDB
FA(18:3n3)HMDB
Chemical FormulaC18H30O2
Average Mass278.4296 Da
Monoisotopic Mass278.22458 Da
IUPAC Name(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Traditional Nameα linolenic acid
CAS Registry Number463-40-1
SMILES
CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O
InChI Identifier
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 KeyDTOSIQBPPRVQHS-PDBXOOCHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abies pinsapoLOTUS Database
Abramis bramaFooDB
Abrus precatoriusLOTUS Database
Abutilon ramosumLOTUS Database
Acacia polyacanthaLOTUS Database
Acanthopanax gracilistylusKNApSAcK Database
AcipenseridaeFooDB
Actinidia chinensisFooDB
Aegle marmelosPlant
Aesculus hippocastanumLOTUS Database
Agaricus bisporusFooDB
Agaricus blazeiLOTUS Database
AgaveFooDB
Agave americanaLOTUS Database
Agave decipiensLOTUS Database
Allamanda catharticaLOTUS Database
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium hirtifoliumPlant
Allium obliquumLOTUS Database
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloe vera var.chinensisKNApSAcK Database
Aloysia triphyllaFooDB
Alpinia oxyphyllaKNApSAcK Database
AmaranthusFooDB
Amaranthus spinosusLOTUS Database
Amaranthus tricolorLOTUS Database
Amelanchier alnifoliaFooDB
Anabaena flos-aquaeKNApSAcK Database
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anthriscus cerefoliumFooDB
Apios americanaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asclepias syriacaLOTUS Database
Asparagus officinalisFooDB
AstacideaFooDB
Astragalus danicusLOTUS Database
Astragalus mongholicusKNApSAcK Database
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaKNApSAcK Database
Azadirachta indicaKNApSAcK Database
Azima tetracanthaLOTUS Database
Basella albaFooDB
Bellis perennisLOTUS Database
Belone beloneFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bidens pilosaLOTUS Database
Boehmeria niveaLOTUS Database
Borago officinalisFooDB
Bos taurusFooDB
BrachyuraFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bryonia albaLOTUS Database
Bupleurum chinenseKNApSAcK Database
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Calophyllum calabaKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Camellia sinensisLOTUS Database
Canarium ovatumFooDB
Canavalia ensiformisLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papayaLOTUS Database
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusKNApSAcK Database
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catharanthus roseusLOTUS Database
Celastrus paniculataLOTUS Database
Celosia cristadaKNApSAcK Database
Centaurea asperaLOTUS Database
Ceratonia siliquaFooDB
Chamaecyparis formosensisLOTUS Database
Chamaemelum nobileKNApSAcK Database
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chlorella vulgarisKNApSAcK Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clitoria ternataKNApSAcK Database
Clitoria ternateaLOTUS Database
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colletia spinosissimaLOTUS Database
Colocasia esculentaFooDB
ColumbidaeFooDB
Consolida regalisLOTUS Database
Corchorus aestuansLOTUS Database
Corchorus olitoriusFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crataegus pinnatifidaKNApSAcK Database
Crateva religiosaFooDB
Crocus sativusFooDB
Crotalaria pallidaLOTUS Database
Croton cortesianusLOTUS Database
Croton tigliumKNApSAcK Database
Cryptomeria japonicaLOTUS Database
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativusLOTUS Database
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita foetidissimaLOTUS Database
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cullen corylifoliumPlant
Cuminum cyminumFooDB
Cuphea epilobiifoliaLOTUS Database
Curcuma longaPlant
Cuscuta pentagonaLOTUS Database
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cystoclonium purpureumLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Dictamnus albusLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dipteryx lacuniferaLOTUS Database
Dolichomitra cymbifoliaLOTUS Database
Drymaria cordataKNApSAcK Database
Drypetes roxburghiiLOTUS Database
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
Echinacea purpureaLOTUS Database
Echium auberianumKNApSAcK Database
Echium boissieriKNApSAcK Database
Echium gentianoidesKNApSAcK Database
Echium giganteumKNApSAcK Database
Echium lusitanicumKNApSAcK Database
Echium pitardiiKNApSAcK Database
Echium plantagineumKNApSAcK Database
Echium sabulicolaKNApSAcK Database
Echium strictumKNApSAcK Database
Echium vulgareKNApSAcK Database
Elaeagnus angustifoliaLOTUS Database
ElaeisFooDB
Elaeis guineensisLOTUS Database
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Elymus repensLOTUS Database
Empetrum nigrumFooDB
EngraulidaeFooDB
Epilobium parviflorumLOTUS Database
Epimedium brevicornumKNApSAcK Database
Eragrostis tefFooDB
Erigeron caucasicusLOTUS Database
Eriobotrya japonicaFooDB
Eruca vesicariaLOTUS Database
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euphausia superbaLOTUS Database
Euphorbia characiasLOTUS Database
Euphorbia glareosaLOTUS Database
Eurhynchium striatumLOTUS Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Fernandoa adenophyllaLOTUS Database
Festuca rubraLOTUS Database
Ficus caricaFooDB
Fimbristylis quinquangularisLOTUS Database
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
Garcinia xanthochymusLOTUS Database
GastropodaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Gleditsia triacanthosLOTUS Database
Glycine maxKNApSAcK Database
Gnetum eduleLOTUS Database
GossypiumFooDB
Gossypium hirsutumLOTUS Database
Gracilaria gracilisLOTUS Database
Grifola frondosaFooDB
Gymnanthemum myrianthumLOTUS Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus porteriLOTUS Database
Helianthus tuberosusFooDB
Hibiscus cannabinusLOTUS Database
Hibiscus sabbariffaFooDB
Hieracium intybaceum All.LOTUS Database
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippophae rhamnoidesKNApSAcK Database
Hirschfeldia incanaLOTUS Database
Homo sapiensLOTUS Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Houttuynia cordataLOTUS Database
Hoya latifoliaLOTUS Database
Hyoscyamus muticusLOTUS Database
Hypericum perforatumLOTUS Database
Hyssopus officinalis L.FooDB
Ictalurus punctatusFooDB
Illicium verumFooDB
Inezia integrifoliaLOTUS Database
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
Isatis tinctoriaLOTUS Database
Jasminum auriculatumKNApSAcK Database
Jodina rhombifoliaLOTUS Database
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactarius deliciosusLOTUS Database
Lactuca sativaFooDB
Lactuca serriolaLOTUS Database
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lallemantia ibericaLOTUS Database
Lallemantia royleanaLOTUS Database
Lantana ukambensisLOTUS Database
Larix gmeliniLOTUS Database
Lathraea squamariaLOTUS Database
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lemna aequinoctialisLOTUS Database
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium meyeniiLOTUS Database
Lepidium meyenii MacaKNApSAcK Database
Lepidium sativumFooDB
LeporidaeFooDB
Leptolyngbya tenuisLOTUS Database
Lepus timidusFooDB
Levisticum officinaleFooDB
Ligularia macrophyllaLOTUS Database
Ligustrum lucidumLOTUS Database
Limanda limandaFooDB
Linum usitatissimumKNApSAcK Database
Litchi chinensisFooDB
Lota lotaFooDB
Luffa acutangulaLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lycium chinenseKNApSAcK Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Macrococculus pomiferusLOTUS Database
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Malva sylvestrisLOTUS Database
Mammea americanaFooDB
Mangifera indicaKNApSAcK Database
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Mikania goyazensisLOTUS Database
Molva molvaFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mosla chinensisLOTUS Database
Mucuna puriensPlant
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa paradisiacaLOTUS Database
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
MytilidaeFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Neolitsea hiiranensisLOTUS Database
Nepeta catariaLOTUS Database
Nephelium lappaceumFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Nervilia aragoanaLOTUS Database
Nicotiana tabacumKNApSAcK Database
Nigella sativaLOTUS Database
Nigella sativa LKNApSAcK Database
Nonea macrospermaLOTUS Database
Nuphar luteaFooDB
Nymphaea albaKNApSAcK Database
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Oecophylla smaragdinaLOTUS Database
Oenothera biennisFooDB
Olea europaeaFooDB
Oleandra wallichiiLOTUS Database
Oncorhynchus gorbuschaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Ononis natrixLOTUS Database
Ophiocordyceps sinensisFungi
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pediomelum esculentumFooDB
Peperomia bracteataLOTUS Database
PerciformesFooDB
Perideridia oreganaFooDB
Perilla frutescensLOTUS Database
Perilla frutescens var.argutaKNApSAcK Database
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Picea jezoensisLOTUS Database
Picea obovataLOTUS Database
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Pinus resinosaLOTUS Database
Pinus sibiricaKNApSAcK Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Plagiochila porelloidesLOTUS Database
Plantago ovataLOTUS Database
Platycodon grandiflorusLOTUS Database
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Polygonum alpinumFooDB
Polypodium aureumLOTUS Database
Pongamia pinnataLOTUS Database
Populus tremulaLOTUS Database
Portulaca oleraceaFooDB
Potentilla asiaticaKNApSAcK Database
Potentilla desertorumKNApSAcK Database
Potentilla orientalisKNApSAcK Database
Poterium polygamum-
Pouteria sapotaFooDB
Premna microphyllaLOTUS Database
Primula pulverulentaLOTUS Database
Prunus armeniacaKNApSAcK Database
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus mumeLOTUS Database
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Pseudostellaria heterophyllaLOTUS Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Psoralea corylifoliaKNApSAcK Database
Punica granatumKNApSAcK Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Rana temporariaLOTUS Database
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Rhodotorula glutinisLOTUS Database
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rosa caninaLOTUS Database
Rosa platyacanthaLOTUS Database
Rosa taiwanensisLOTUS Database
Rosa transmorrisonensisLOTUS Database
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Saccharina japonicaFooDB
Sagittaria latifoliaFooDB
Salix herbaceaLOTUS Database
Salix pulchraFooDB
Salmea scandensLOTUS Database
Salmo salarFooDB
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia elegansFooDB
Salvia fruticosaLOTUS Database
Salvia hispanicaFooDB
Salvia miltiorrhizaLOTUS Database
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Salvia trijugaLOTUS Database
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Saussurea medusaLOTUS Database
Schotia brachypetalaLOTUS Database
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Scrophularia nodosaLOTUS Database
Scurrula atropurpureaKNApSAcK Database
Scurrura atropurpurea-
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Senna alexandrinaLOTUS Database
Senna didymobotryaLOTUS Database
Serenoa repensLOTUS Database
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Sideritis tauricaLOTUS Database
SiluriformesFooDB
Silybum marianumKNApSAcK Database
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Sterculia tragacanthaLOTUS Database
Stilpnopappus tomentosusLOTUS Database
Stuckenia pectinataLOTUS Database
Suaeda aegyptiacaLOTUS Database
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Talaromyces flavusLOTUS Database
Tamarindus indicaFooDB
Taonia atomariaLOTUS Database
Taraxacum officinaleFooDB
Taxus maireiLOTUS Database
Tetragonia tetragonioidesFooDB
Thalictrum revolutumLOTUS Database
ThelespermaFooDB
Theobroma cacaoFooDB
ThunnusFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia cordata Mill.KNApSAcK Database
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Treculia africanaLOTUS Database
Trichosanthes kirilowiiKNApSAcK Database
Trichosanthes rosthorniiKNApSAcK Database
Trifolium alexandrinumLOTUS Database
Trigonella foenum-graecumFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumKNApSAcK Database
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
Typha domingensisLOTUS Database
Typha domingensis P.KNApSAcK Database
Ulva fasciataLOTUS Database
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Ventilago denticulataLOTUS Database
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaKNApSAcK Database
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna subterraneaLOTUS Database
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Vitellaria paradoxaFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Wedelia calycinaLOTUS Database
Withania somniferaPlant
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus spina-christiLOTUS Database
Ziziphus zizyphusFooDB
Species Where Detected
Species NameSourceReference
Cordyceps sinensisKNApSAcK Database
Homo sapiens (Serum)KNApSAcK Database
Psalliota bisporaKNApSAcK Database
Chemical 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Long-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-16.5 °CNot Available
Boiling Point230.00 to 231.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility0.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.46Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility0.00027 g/LALOGPS
logP6.62ALOGPS
logP6.06ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity89.64 m³·mol⁻¹ChemAxon
Polarizability34.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001388
DrugBank IDDB00132
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031277
KNApSAcK IDC00007247
Chemspider ID4444437
KEGG Compound IDC06427
BioCyc IDLINOLENIC_ACID
BiGG ID48237
Wikipedia LinkAlpha-Linolenic_acid
METLIN ID6208
PubChem Compound5280934
PDB IDNot Available
ChEBI ID27432
Good Scents IDrw1045911
References
General References
  1. Richieri GV, Ogata RT, Kleinfeld AM: Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB. J Biol Chem. 1994 Sep 30;269(39):23918-30. [PubMed:7929039 ]
  2. Bajaj M, Suraamornkul S, Romanelli A, Cline GW, Mandarino LJ, Shulman GI, DeFronzo RA: Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients. Diabetes. 2005 Nov;54(11):3148-53. [PubMed:16249438 ]
  3. Christensen JH, Fabrin K, Borup K, Barber N, Poulsen J: Prostate tissue and leukocyte levels of n-3 polyunsaturated fatty acids in men with benign prostate hyperplasia or prostate cancer. BJU Int. 2006 Feb;97(2):270-3. [PubMed:16430627 ]
  4. Attar-Bashi NM, Frauman AG, Sinclair AJ: Alpha-linolenic acid and the risk of prostate cancer. What is the evidence? J Urol. 2004 Apr;171(4):1402-7. [PubMed:15017185 ]
  5. Rastogi SK, Singh J: Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis. Pharm Dev Technol. 2005;10(1):97-104. [PubMed:15776817 ]
  6. Allman MA, Pena MM, Pang D: Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. Eur J Clin Nutr. 1995 Mar;49(3):169-78. [PubMed:7774533 ]
  7. Fokkema MR, Brouwer DA, Hasperhoven MB, Martini IA, Muskiet FA: Short-term supplementation of low-dose gamma-linolenic acid (GLA), alpha-linolenic acid (ALA), or GLA plus ALA does not augment LCP omega 3 status of Dutch vegans to an appreciable extent. Prostaglandins Leukot Essent Fatty Acids. 2000 Nov;63(5):287-92. [PubMed:11090255 ]
  8. Becker CC, Lund P, Holmer G, Jensen H, Sandstrom B: Effects of butter oil blends with increased concentrations of stearic, oleic and linolenic acid on blood lipids in young adults. Eur J Clin Nutr. 1999 Jul;53(7):535-41. [PubMed:10452408 ]
  9. Jones DB, Scaretto L, Carter R, Mann JI: Glucose, insulin and platelet fatty acids following myocardial infarction: an association with infarct size. Diabete Metab. 1987 Jul-Aug;13(4):463-6. [PubMed:3315767 ]
  10. Crastes de Paulet A, Babin F, Billeaud C, Bougle D, Sarda P, Mendy F: [Biological effects on premature neonates of a milk formula enriched with alpha-linolenic acid: a multicenter study]. Bull Acad Natl Med. 1994 Feb;178(2):267-73; discussion 273-8. [PubMed:7913655 ]
  11. Li D, Sinclair A, Wilson A, Nakkote S, Kelly F, Abedin L, Mann N, Turner A: Effect of dietary alpha-linolenic acid on thrombotic risk factors in vegetarian men. Am J Clin Nutr. 1999 May;69(5):872-82. [PubMed:10232625 ]
  12. Bhatia KS, Singh J: Effect of linolenic acid/ethanol or limonene/ethanol and iontophoresis on the in vitro percutaneous absorption of LHRH and ultrastructure of human epidermis. Int J Pharm. 1999 Apr 15;180(2):235-50. [PubMed:10370194 ]
  13. Baylin A, Kabagambe EK, Ascherio A, Spiegelman D, Campos H: Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica. Circulation. 2003 Apr 1;107(12):1586-91. Epub 2003 Mar 10. [PubMed:12668490 ]
  14. Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8. [PubMed:11290821 ]
  15. Campbell FM, Gordon MJ, Dutta-Roy AK: Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes. Mol Cell Biochem. 1996 Feb 9;155(1):77-83. [PubMed:8717442 ]
  16. Cunnane SC, Hamadeh MJ, Liede AC, Thompson LU, Wolever TM, Jenkins DJ: Nutritional attributes of traditional flaxseed in healthy young adults. Am J Clin Nutr. 1995 Jan;61(1):62-8. [PubMed:7825540 ]
  17. Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. [PubMed:10617967 ]
  18. Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. [PubMed:10775263 ]
  19. Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. [PubMed:11157315 ]
  20. Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. [PubMed:12438303 ]
  21. Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. [PubMed:15051847 ]