Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Created at2005-11-16 15:48:42 UTC
Updated at2024-04-09 04:10:35 UTC
NP-MRD IDNP0000315
Secondary Accession NumbersNone
Natural Product Identification
Common NameMyristic acid
DescriptionMyristic acid, also known as tetradecanoic acid or C14:0, 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. Myristic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, it is a very hydrophobic molecule that is practically insoluble in water. It exists as an oily white crystalline solid. Myristic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. Industrially, myristic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). Within eukaryotic cells, myristic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). Myristic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. Also, this fatty acid is known because it accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health (see, for example, PMID: 15936650 ). Myristic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair.
1-Tetradecanecarboxylic acidChEBI
Acide tetradecanoiqueChEBI
N-Tetradecan-1-Oic acidChEBI
N-Tetradecanoic acidChEBI
N-Tetradecoic acidChEBI
Tetradecoic acidChEBI
Tetradecanoic acidGenerator
1-Tridecanecarboxylic acidHMDB
Myristic acid pureHMDB
Myristoic acidHMDB
Tetradecanoic (myristic) acidHMDB
Acid, tetradecanoicHMDB
Acid, myristicHMDB
Chemical FormulaC14H28O2
Average Mass228.3709 Da
Monoisotopic Mass228.20893 Da
IUPAC Nametetradecanoic acid
Traditional Namemyristic acid
CAS Registry Number544-63-8
InChI Identifier
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-24View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-07-24View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abies pinsapoLOTUS Database
Abramis bramaFooDB
Abrus precatoriusLOTUS Database
Abutilon ramosumLOTUS Database
Acacia auriculiformisLOTUS Database
Achillea fragrantissimaLOTUS Database
Achyranthes asperaLOTUS Database
Aconitum japonicumLOTUS Database
Acorus calamusLOTUS Database
Actinidia chinensisFooDB
Aesculus hippocastanumLOTUS Database
Agaricus bisporusFooDB
Agave decipiensLOTUS Database
Agelas coniferaLOTUS Database
Aleuroglyphus ovatusLOTUS Database
Allium ampeloprasumLOTUS Database
Allium cepaFooDB
Allium cepa L.FooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Althaea officinalisLOTUS Database
Amaranthus caudatusLOTUS Database
Amaranthus retroflexusLOTUS Database
Amphimedon compressaLOTUS Database
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
Anas platyrhynchosFooDB
Anethum graveolensFooDB
Angelica sinensisPlant
Anisophyllea laurinaLOTUS Database
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Anser anserFooDB
Anthemis aciphyllaLOTUS Database
Anthemis aciphylla BOISS.var.discoidea BOISSPlant
Anthriscus cerefoliumFooDB
Antirrhinum majusLOTUS Database
Apis ceranaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Aplysina archeriLOTUS Database
Arabidopsis thalianaPlant
Arachis hypogaeaFooDB
Arbacia punctulataLOTUS Database
Arctium lappaFooDB
Areca catechuPlant
Arisaema tortuosumLOTUS Database
Armoracia rusticanaFooDB
Arnica montanaLOTUS Database
Artemisia capillarisPlant
Artemisia monospermaLOTUS Database
Asparagus officinalisFooDB
Astragalus hamosusLOTUS Database
Attalea colendaLOTUS Database
Attalea speciosaLOTUS Database
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Azima tetracanthaLOTUS Database
Basella albaLOTUS Database
Bellis perennisLOTUS Database
Belone beloneFooDB
Bergera koenegii-
Bertholletia excelsaFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Bombax ceibaLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. rapaFooDB
Brunfelsia americanaLOTUS Database
Bubalus bubalisFooDB
Cachrys siculaLOTUS Database
Callyspongia fallaxLOTUS Database
Calophyllum calabaPlant
Calophyllum inophyllumPlant
Camellia sinensisLOTUS Database
Canarium albumLOTUS Database
Canavalia ensiformisLOTUS Database
Cancer magisterFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carica papayaLOTUS Database
Carica papaya L.FooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
Carya illinoinensisFooDB
Cassia javanicaLOTUS Database
Catharanthus roseusLOTUS Database
Celosia cristadaPlant
Ceratonia siliquaFooDB
Cervicornia cuspidiferaLOTUS Database
Cervus canadensisFooDB
Chenopodium quinoaFooDB
Chionoecetes opilioFooDB
Chlamydomonas reinhardtiiLOTUS Database
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
Cinnamomum parthenoxylonLOTUS Database
Cinnamomum verumFooDB
Cistus creticusPlant
Cistus incanusLOTUS Database
Citrullus colocynthisPlant
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cleome amblyocarpaLOTUS Database
Cocos nuciferaFooDB
Codonopsis pilosulaPlant
Coffea arabica L.FooDB
Coffea canephoraFooDB
Conioselinum vaginatumPlant
Cordia sinensisLOTUS Database
Coriandrum sativumLOTUS Database
Coriandrum sativum L.FooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crotalaria pallidaLOTUS Database
Croton tigliumPlant
Cryptomeria japonicaLOTUS Database
Cryptostegia grandifloraLOTUS Database
Cucumis meloFooDB
Cucumis sativusLOTUS Database
Cucumis sativus L.FooDB
Cucurbita foetidissimaLOTUS Database
Cucurbita maximaFooDB
Cullen corylifoliumPlant
Cuphea carthagenensisLOTUS Database
Curcuma amanda RoxbPlant
Curcuma longaLOTUS Database
Cyamopsis tetragonolobaLOTUS Database
Cydonia oblongaFooDB
Cynara scolymusFooDB
Cystoclonium purpureumLOTUS Database
Daphne odoraLOTUS Database
Daphnia magnaLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Delonix regiaLOTUS Database
Diascia cordataPlant
Diascia integerrimaPlant
Diascia megathuraPlant
Diascia purpureaPlant
Diascia vigilisPlant
Dictamnus albusLOTUS Database
Dromaius novaehollandiaeFooDB
Drymaria cordataPlant
Dryopteris carthusianaLOTUS Database
Duhaldea cappaLOTUS Database
Elaeagnus angustifoliaLOTUS Database
Elaeis guineensisLOTUS Database
Elettaria cardamomumFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Erigeron caucasicusLOTUS Database
Erigeron philadelphicusLOTUS Database
Eriobotrya japonicaFooDB
Erucaria microcarpaLOTUS Database
Erylus formosusLOTUS Database
Erythrina suberosaLOTUS Database
Esox luciusFooDB
Etlingera elatiorLOTUS Database
Euphausia superbaLOTUS Database
Fagopyrum esculentumFooDB
Fernandoa adenophyllaLOTUS Database
Ficus caricaFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Frullania anomalaPlant
Frullania incumbensPlant
Frullania lobulataPlant
Frullania probosciphoraPlant
Frullania scandensPlant
Frullania spiniferaPlant
Fumaria vaillantiiLOTUS Database
Gallus gallusFooDB
Ganoderma australeLOTUS Database
Ganoderma lucidumFungi
Garcinia xanthochymusLOTUS Database
Ginkgo bilobaFooDB
Giraffa camelopardalisLOTUS Database
Gladiolus italicusLOTUS Database
Glycine maxFooDB
Glycyrrhiza glabraLOTUS Database
Gnetum eduleLOTUS Database
Gossypium hirsutumLOTUS Database
Gryllotalpa orientalisLOTUS Database
Gymnodinium nagasakienseLOTUS Database
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus cannabinusLOTUS Database
Hibiscus sabbariffaFooDB
Hibiscus sabdariffaLOTUS Database
Hibiscus syriacusLOTUS Database
Hippoglossus hippoglossusFooDB
Hippophae rhamnoidesLOTUS Database
Hipppophae rhamnoides-
Hirschfeldia incanaLOTUS Database
Homo sapiens (Serum)Animalia
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Horsfieldia iryaLOTUS Database
Houttuynia cordataPlant
Houttuynia emeiensisPlant
Hoya longifoliaLOTUS Database
Hydnora johannisLOTUS Database
Hyoscyamus nigerPlant
Hypericum olympicumLOTUS Database
Hypericum perfoliatumLOTUS Database
Ictalurus punctatusFooDB
Inula britannica var.chinensisPlant
Inula grandisLOTUS Database
Inula heleniumLOTUS Database
Ipomoea batatasFooDB
Iris flomentinaPlant
Iris florentinaPlant
Iris tectorumLOTUS Database
Irvingia gabonensisLOTUS Database
Isatis tinctoriaLOTUS Database
Ixora coccineaLOTUS Database
Jasminum fluminenseLOTUS Database
Jatropha gossypifoliaLOTUS Database
Juglans nigra L.FooDB
Juglans regiaFooDB
Juniperus phoeniceaLOTUS Database
Katsuwonus pelamisFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lactuca serriolaLOTUS Database
Lagopus mutaFooDB
Lantana camaraLOTUS Database
Lathraea squamariaLOTUS Database
Lens culinarisFooDB
Lepidium meyeniiLOTUS Database
Lepidium sativumFooDB
Lepomis gibbosusFooDB
Leptolyngbya tenuisLOTUS Database
Lepus timidusFooDB
Levisticum officinaleFooDB
Limanda limandaFooDB
Lindera neesianaLOTUS Database
Linum usitatissimumFooDB
Litchi chinensisFooDB
Litsea monopetalaPlant
Lota lotaFooDB
Lumbricus terrestrisLOTUS Database
Lupinus albusFooDB
Macadamia integrifoliaLOTUS Database
Malus pumilaFooDB
Malva sylvestrisLOTUS Database
Malvaviscus arboreusLOTUS Database
Mandragora autumnalisPlant
Mandragora officinarumLOTUS Database
Mangifera indicaFooDB
Manihot esculentaFooDB
Maranta arundinaceaFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Mikania cordifoliaLOTUS Database
Mitracarpus hirtusLOTUS Database
Molva molvaFooDB
Momordica charantiaFooDB
Moringa oleiferaFooDB
Mucuna puriensPlant
Murraya paniculataPlant
Musa paradisiacaLOTUS Database
Musa x paradisiacaFooDB
Mycoplasmopsis bovisLOTUS Database
Myristica fragransFooDB
Myristica moschataPlant
Myrmekioderma reaLOTUS Database
Nanodea muscosaLOTUS Database
Narthecium ossifragumLOTUS Database
Nelumbo luteaLOTUS Database
Nelumbo nuciferaFooDB
Nepeta catariaLOTUS Database
Nephrops norvegicusFooDB
Nierembergia aristataLOTUS Database
Nigella sativaLOTUS Database
Nigrospora sphaericaLOTUS Database
Notopterygium incisumPlant
Numida meleagrisFooDB
Nuphar luteaFooDB
Nymphaea albaPlant
Octopus vulgarisFooDB
Oecophylla smaragdinaLOTUS Database
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
Ononis natrixLOTUS Database
Origanum vulgareFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Pandanus conoideus LamPlant
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Pelargonium endlicherianumLOTUS Database
Pentaclethra macrophyllaLOTUS Database
Perilla frutescensLOTUS Database
Persea americanaFooDB
Persicaria minorLOTUS Database
Petroselinum crispumFooDB
Phagnalon sordidumPlant
Phaseolus coccineusLOTUS Database
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Phyllostachys edulisFooDB
Phytolacca acinosaLOTUS Database
Pimpinella anisumFooDB
Pinus pumilaLOTUS Database
Pinus radiataLOTUS Database
Pinus sibiricaPlant
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Plantago lanceolataPlant
Plantago majorPlant
Plantago ovataLOTUS Database
Pleurotus ostreatusFooDB
Plumeria rubraLOTUS Database
Polygala senegaLOTUS Database
Polygonum minusPlant
Portulaca oleraceaFooDB
Primula ovalifoliaPlant
Proiphys amboinensisLOTUS Database
Prunus africanaLOTUS Database
Prunus armeniacaFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Rehmannia glutinosaPlant
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Rhodiola roseaPlant
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Rosa platyacanthaLOTUS Database
Ruellia tuberosaLOTUS Database
Rumex acetosaFooDB
Saccharina japonicaFooDB
Salmo salarFooDB
Salmonella entericaLOTUS Database
Salpa thompsoniLOTUS Database
Salvadora oleoidesLOTUS Database
Salvelinus namaycushFooDB
Salvia fruticosaLOTUS Database
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Santalum albumPlant
Saussurea involucrataLOTUS Database
Saxifraga stoloniferaLOTUS Database
Saxifraga stolonifera Meerb.Plant
Scolochloa festucaceaLOTUS Database
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
Scutellaria baicalensisLOTUS Database
Scytosiphon lomentariaLOTUS Database
Sebastes alutusFooDB
Sebastes viviparusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Senecio vulgarisPlant
Senna alexandrinaLOTUS Database
Serenoa repensLOTUS Database
Sesamum indicumFooDB
Sideritis montanaLOTUS Database
Sideritis tauricaLOTUS Database
Silybum marianumLOTUS Database
Sinapis albaFooDB
Smenospongia aureaLOTUS Database
Solanum chacoenseLOTUS Database
Solanum lycopersicumFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum tuberosumFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Spongiporus leucomallellus (Murril)-
Squalus acanthiasFooDB
Stenodus leucichthysFooDB
Sterculia tragacanthaLOTUS Database
Streptomyces rocheiLOTUS Database
Struthio camelusFooDB
Stuckenia pectinataLOTUS Database
Suaeda aegyptiacaLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium cuminiLOTUS Database
Talaromyces flavusLOTUS Database
Tamarindus indicaFooDB
Tanacetum macrophyllumPlant
Taonia atomariaLOTUS Database
Taraxacum officinaleFooDB
Taxus baccataPlant
Terminalia pallidaLOTUS Database
Tetragonia tetragonioidesFooDB
Thalictrum revolutumLOTUS Database
Thunnus albacaresFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia tomentosaLOTUS Database
Tipuana tipuPlant
Tordylium apulumLOTUS Database
Trichodesma zeylanicumLOTUS Database
Trichosanthes kirilowiiPlant
Trichosanthes rosthorniiPlant
Trifolium pratenseLOTUS Database
Tripneustes ventricosusLOTUS Database
Trisopterus esmarkiiFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Triticum turgidumLOTUS Database
Tritrichomonas suisLOTUS Database
Turnera ulmifoliaLOTUS Database
Vaccinium macrocarponFooDB
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaFooDB
Vernonanthura chamaedrysLOTUS Database
Viburnum opulusLOTUS Database
Vicia fabaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Virola bicuhybaLOTUS Database
Virola surinamensisFooDB
Vitellaria paradoxaFooDB
Vitex trifoliaPlant
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Xestospongia mutaLOTUS Database
Zea mays L.FooDB
Zingiber officinaleFooDB
Ziziphus jujubaPlant
Ziziphus spina-christiLOTUS Database
Chemical 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
  • Long-chain 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
Experimental Properties
Melting Point53.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0011 mg/mLNot Available
LogP6.11Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
Water Solubility0.0017 g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity67.88 m³·mol⁻¹ChemAxon
Polarizability30.1 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDDB08231
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031009
KNApSAcK IDC00001228
Chemspider ID10539
KEGG Compound IDC06424
BioCyc IDCPD-7836
BiGG ID215851
Wikipedia LinkMyristic_acid
PubChem Compound11005
PDB IDNot Available
ChEBI ID28875
Good Scents IDrw1009061
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
  3. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  4. Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. [PubMed:11124748 ]
  5. Dabadie H, Peuchant E, Bernard M, LeRuyet P, Mendy F: Moderate intake of myristic acid in sn-2 position has beneficial lipidic effects and enhances DHA of cholesteryl esters in an interventional study. J Nutr Biochem. 2005 Jun;16(6):375-82. [PubMed:15936650 ]
  6. Majeti BK, Karmali PP, Madhavendra SS, Chaudhuri A: Example of fatty acid-loaded lipoplex in enhancing in vitro gene transfer efficacies of cationic amphiphile. Bioconjug Chem. 2005 May-Jun;16(3):676-84. [PubMed:15898737 ]
  7. Schewe T, Hiebsch C: [Action of respiratory inhibitors on the electron transport system of Escherichia coli]. Acta Biol Med Ger. 1977;36(7-8):961-6. [PubMed:347849 ]
  8. Curry S, Brick P, Franks NP: Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim Biophys Acta. 1999 Nov 23;1441(2-3):131-40. [PubMed:10570241 ]
  9. Kageura M, Hara K, Hieda Y, Takamoto M, Fujiwara Y, Fukuma Y, Kashimura S: [Screening of drugs and chemicals by wide-bore capillary gas chromatography with flame ionization and nitrogen phosphorus detectors]. Nihon Hoigaku Zasshi. 1989 Apr;43(2):161-5. [PubMed:2810891 ]
  10. Zhu W, Smart EJ: Myristic acid stimulates endothelial nitric-oxide synthase in a CD36- and an AMP kinase-dependent manner. J Biol Chem. 2005 Aug 19;280(33):29543-50. Epub 2005 Jun 21. [PubMed:15970594 ]
  11. Bhattacharya A, Ghosal SK: Permeation kinetics of ketotifen fumarate alone and in combination with hydrophobic permeation enhancers through human cadaver epidermis. Boll Chim Farm. 2000 Jul-Aug;139(4):177-81. [PubMed:11059101 ]
  12. Matsubara M: [Structures and molecular recognition of MARCKS family proteins]. Seikagaku. 2005 Jan;77(1):50-5. [PubMed:15770953 ]
  13. Kaminskas A, Zieden B, Elving B, Kristenson M, Abaravicius A, Bergdahl B, Olsson AG, Kucinskiene Z: Adipose tissue fatty acids in men from two populations with different cardiovascular risk: the LiVicordia study. Scand J Clin Lab Invest. 1999 May;59(3):227-32. [PubMed:10400167 ]
  14. Brod SA, Malone M, Darcan S, Papolla M, Nelson L: Ingested interferon alpha suppresses type I diabetes in non-obese diabetic mice. Diabetologia. 1998 Oct;41(10):1227-32. [PubMed:9794112 ]
  15. Pieterse Z, Jerling JC, Oosthuizen W, Kruger HS, Hanekom SM, Smuts CM, Schutte AE: Substitution of high monounsaturated fatty acid avocado for mixed dietary fats during an energy-restricted diet: effects on weight loss, serum lipids, fibrinogen, and vascular function. Nutrition. 2005 Jan;21(1):67-75. [PubMed:15661480 ]