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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:31:55 UTC
HMDB IDHMDB0000806
Secondary Accession Numbers
  • HMDB00806
Metabolite 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.
Structure
Data?1582752157
Synonyms
ValueSource
1-Tetradecanecarboxylic acidChEBI
14ChEBI
14:0ChEBI
14:00ChEBI
Acide tetradecanoiqueChEBI
C14ChEBI
CH3-[CH2]12-COOHChEBI
MyristinsaeureChEBI
N-Tetradecan-1-Oic acidChEBI
N-Tetradecanoic acidChEBI
N-Tetradecoic acidChEBI
Tetradecoic acidChEBI
TetradecanoateKegg
1-TetradecanecarboxylateGenerator
N-Tetradecan-1-OateGenerator
N-TetradecanoateGenerator
N-TetradecoateGenerator
TetradecoateGenerator
Tetradecanoic acidGenerator
MyristateGenerator
1-TridecanecarboxylateHMDB
1-Tridecanecarboxylic acidHMDB
CrodacidHMDB
Myristic acid pureHMDB
MyristoateHMDB
Myristoic acidHMDB
Tetradecanoic (myristic) acidHMDB
Acid, tetradecanoicHMDB
Acid, myristicHMDB
FA(14:0)HMDB
Chemical FormulaC14H28O2
Average Molecular Weight228.3709
Monoisotopic Molecular Weight228.20893014
IUPAC Nametetradecanoic acid
Traditional Namemyristic acid
CAS Registry Number544-63-8
SMILES
CCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
InChI KeyTUNFSRHWOTWDNC-UHFFFAOYSA-N
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
Substituents
  • 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point53.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0011 mg/mLNot Available
LogP6.11SANGSTER (1993)
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP6.1ALOGPS
logP5.37ChemAxon
logS-5.1ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalMetCCS_train_neg159.20930932474
AllCCS[M-H]-ExperimentalNot Available159.209http://allccs.zhulab.cn/database/detail?ID=AllCCS00000218
DarkChem[M+H]+PredictedNot Available159.59531661259
DarkChem[M-H]-PredictedNot Available158.27431661259
AllCCS[M+H]+PredictedNot Available162.22932859911
AllCCS[M-H]-PredictedNot Available162.93432859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Myristic acid,1TMS,#11846.0762https://arxiv.org/abs/1905.12712
Myristic acid,1TBDMS,#12085.6768https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-2910000000-66b35fb8449ba9de9cd62014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017i-2910000000-66b35fb8449ba9de9cd62017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-f45703c464ca75f98f262017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-ec8d81e37bc3b8531c992016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9330000000-5ec01705dfacc992be282017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-06xx-9200000000-4fdd41f0461ff51869012014-09-20View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0090000000-73ac1cfb8731e6318cc52012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-1090000000-3aa768974da0ea81c1c92012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-22cd107a87b9acf058c52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-2f7bb32e4b42206d851d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-2090000000-d45cffc15e2efbd45cd62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9200000000-dbca68238dfebab352512012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004r-9000000000-26827be8f8c2a4fbfd752012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-91f4f874b25705464fb02017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-15225a799e0a0bcff7c72017-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-b88426a2003ceec57e302015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5940000000-6c73dc0032502abe4fc42015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-bde9bfcd2889066fc8532015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-b88426a2003ceec57e302015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5940000000-6c73dc0032502abe4fc42015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-bde9bfcd2889066fc8532015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-a32f141c7b5af0bc4de12015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1490000000-14bfb0d0344d7cf634432015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-512abb1322963024336f2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-a32f141c7b5af0bc4de12015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1490000000-14bfb0d0344d7cf634432015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-512abb1322963024336f2015-05-27View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Placenta
  • Prostate
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified25.0 (8.0-70.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.0 +/- 1.3 uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified7.16 +/- 3 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified9.3 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified15.464 +/- 4.024 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.7 +/- 1.5 uMAdolescent (13-18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified2.1 +/- 0.9 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.1-3.3 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified13.137 +/- 0.438 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified13.137 +/- 4.379 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified13.137 +/- 4.379 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified13.137 +/- 4.379 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified18.610 +/- 6.919 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified90 +/- 40 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified90 +/- 20 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified6.06 +/- 0.069 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified5.0 +/- 5.0 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected and Quantified2.846 +/- 7.0937 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.06 +/- 0.03 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Oesophageal cancer
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral leukoplakia (OLK) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Colorectal cancer
  1. Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ]
  2. Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ]
  3. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  4. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  5. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  6. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
  7. Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Associated OMIM IDs
DrugBank IDDB08231
Phenol Explorer Compound IDNot Available
FooDB IDFDB031009
KNApSAcK IDC00001228
Chemspider ID10539
KEGG Compound IDC06424
BioCyc IDCPD-7836
BiGG ID215851
Wikipedia LinkMyristic_acid
METLIN ID196
PubChem Compound11005
PDB IDNot Available
ChEBI ID28875
Food Biomarker OntologyNot Available
VMH IDTTDCA
MarkerDB IDNot Available
References
Synthesis ReferenceGreaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L. Anodic syntheses. I. New syntheses of stearic, myristic, and other acids. Journal of the Chemical Society (1950), 3326-30.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Matsubara M: [Structures and molecular recognition of MARCKS family proteins]. Seikagaku. 2005 Jan;77(1):50-5. [PubMed:15770953 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 68 proteins in total.

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06
Reactions
Tetradecanoyl-[acp] + Water → Acyl-carrier protein + Myristic aciddetails
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in sugar binding
Specific function:
Has lysophospholipase activity.
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Molecular weight:
16118.44
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Molecular weight:
21066.99
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5

Only showing the first 10 proteins. There are 68 proteins in total.