Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:22 UTC
HMDB IDHMDB00806
Secondary Accession NumbersNone
Metabolite Identification
Common NameMyristic acid
DescriptionMyristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. this is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.(wikipedia).
Structure
Thumb
Synonyms
  1. 1-Tridecanecarboxylate
  2. 1-Tridecanecarboxylic acid
  3. Crodacid
  4. Myristate
  5. Myristic acid
  6. Myristic acid pure
  7. Myristoate
  8. Myristoic acid
  9. N-Tetradecan-1-oate
  10. N-Tetradecan-1-oic acid
  11. N-Tetradecanoate
  12. N-Tetradecanoic acid
  13. Tetradecanoate
  14. Tetradecanoic (Myristic) acid
  15. Tetradecanoic acid
Chemical FormulaC14H28O2
Average Molecular Weight228.3709
Monoisotopic Molecular Weight228.20893014
IUPAC Nametetradecanoic acid
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassStraight Chain Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Saturated fatty acids(KEGG)
  • Straight chain fatty acids(KEGG)
  • Straight chain fatty acids(Lipidmaps)
  • long-chain fatty acid(ChEBI)
  • straight-chain saturated fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct ParentStraight Chain Fatty Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point53.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00107 mg/mLNot Available
LogP6.11SANGSTER (1993)
Predicted 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 area37.3ChemAxon
rotatable bond count12ChemAxon
refractivity67.88ChemAxon
polarizability30.1ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Epidermis
  • Prostate
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified25.0 (8.0-70.0) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified3.0 +/- 1.3 uMChildren (1-13 year old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified7.16 +/- 3 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified9.3 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified15.464 +/- 4.024 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified2.7 +/- 1.5 uMAdolescent (13-18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified2.1 +/- 0.9 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified6.06 +/- 0.069 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified5.0 +/- 5.0 uMAdult (>18 years old)Not SpecifiedNormal
UrineDetected and Quantified0.06 +/- 0.03 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002890
KNApSAcK IDC00001228
Chemspider ID10539
KEGG Compound IDC06424
BioCyc IDNot Available
BiGG ID215851
Wikipedia LinkMyristic acid
NuGOwiki LinkHMDB00806
Metagene LinkHMDB00806
METLIN ID196
PubChem Compound11005
PDB IDMYR
ChEBI ID28875
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)Not Available
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. 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

Only showing the first 50 proteins. There are 68 proteins in total.

Enzymes

Gene Name:
FASN
Uniprot ID:
P49327
Reactions
Tetradecanoyl-[acp] + Water unknown Acyl-carrier protein + Myristic aciddetails
Gene Name:
PLA2G5
Uniprot ID:
P39877
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Gene Name:
PLA2G10
Uniprot ID:
O15496
Gene Name:
LGALS13
Uniprot ID:
Q9UHV8
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Gene Name:
CLC
Uniprot ID:
Q05315
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Gene Name:
PNLIP
Uniprot ID:
P16233
Gene Name:
LIPC
Uniprot ID:
P11150
Gene Name:
LIPF
Uniprot ID:
P07098
Gene Name:
LIPG
Uniprot ID:
Q9Y5X9
Gene Name:
CEL
Uniprot ID:
P19835
Gene Name:
PNLIPRP2
Uniprot ID:
P54317
Gene Name:
LPL
Uniprot ID:
P06858
Gene Name:
CES1
Uniprot ID:
P23141
Gene Name:
CES2
Uniprot ID:
O00748
Gene Name:
BCHE
Uniprot ID:
P06276
Gene Name:
PLA2G4C
Uniprot ID:
Q9UP65
Gene Name:
LIPE
Uniprot ID:
Q05469
Gene Name:
PLA2G3
Uniprot ID:
Q9NZ20
Gene Name:
ACYP2
Uniprot ID:
P14621
Gene Name:
ACYP1
Uniprot ID:
P07311
Gene Name:
ACY1
Uniprot ID:
Q03154
Gene Name:
ASPA
Uniprot ID:
P45381
Gene Name:
ACY3
Uniprot ID:
Q96HD9
Gene Name:
PPT2
Uniprot ID:
Q9UMR5
Gene Name:
ASAH1
Uniprot ID:
Q13510
Gene Name:
SLC27A6
Uniprot ID:
Q9Y2P4
Gene Name:
SLC27A3
Uniprot ID:
Q5K4L6
Gene Name:
SLC27A4
Uniprot ID:
Q6P1M0
Gene Name:
ASPG
Uniprot ID:
Q86U10
Gene Name:
PLA2G4D
Uniprot ID:
Q86XP0
Gene Name:
PLA2G4E
Uniprot ID:
Q3MJ16
Gene Name:
PLA2G4F
Uniprot ID:
Q68DD2
Gene Name:
PLA2G4B
Uniprot ID:
P0C869

Transporters

Only showing the first 50 proteins. There are 68 proteins in total.