Human Metabolome Database Version 3.5

Showing metabocard for Myristic acid (HMDB00806)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:22 -0700
HMDB ID HMDB00806
Secondary Accession Numbers None
Metabolite Identification
Common Name Myristic acid
Description Myristic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C14H28O2
Average Molecular Weight 228.3709
Monoisotopic Molecular Weight 228.20893014
IUPAC Name tetradecanoic acid
Traditional IUPAC Name myristic acid
CAS Registry Number 544-63-8
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 Key TUNFSRHWOTWDNC-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Straight 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 Parent Straight Chain Fatty Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 53.9 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.00107 mg/mL Not Available
LogP 6.11 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 0.0017 g/L ALOGPS
LogP 6.10 ALOGPS
LogP 5.37 ChemAxon
LogS -5.12 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 67.88 ChemAxon
Polarizability 30.1 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Epidermis
  • Prostate
  • Adipose Tissue
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Fatty Acid Biosynthesis SMP00456 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
25.0 (8.0-70.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
3.0 +/- 1.3 uM Children (1-13 year old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
7.16 +/- 3 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
9.3 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
15.464 +/- 4.024 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
2.7 +/- 1.5 uM Adolescent (13-18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
2.1 +/- 0.9 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
6.06 +/- 0.069 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
5.0 +/- 5.0 uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
0.06 +/- 0.03 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB002890
KNApSAcK ID C00001228 Link_out
Chemspider ID 10539 Link_out
KEGG Compound ID C06424 Link_out
BioCyc ID Not Available
BiGG ID 215851 Link_out
Wikipedia Link Myristic acid Link_out
NuGOwiki Link HMDB00806 Link_out
Metagene Link HMDB00806 Link_out
METLIN ID 196 Link_out
PubChem Compound 11005 Link_out
PDB ID MYR Link_out
ChEBI ID 28875 Link_out
References
Synthesis Reference Greaves, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  9. Matsubara M: [Structures and molecular recognition of MARCKS family proteins] Seikagaku. 2005 Jan;77(1):50-5. Pubmed: 15770953 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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. Pubmed: 19212411 Link_out

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 67 enzymes in total.

Name: Fatty acid synthase
Reactions:
Tetradecanoyl-[acp] + Water unknown Acyl-carrier protein + Myristic acid details
Gene Name: FASN
Uniprot ID: P49327 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calcium-dependent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G5
Uniprot ID: P39877 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIF secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2F
Uniprot ID: Q9BZM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2
Reactions: Not Available
Gene Name: PLA2G4A
Uniprot ID: P47712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2
Reactions: Not Available
Gene Name: PLA2G1B
Uniprot ID: P04054 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 10 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G10
Uniprot ID: O15496 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactoside-binding soluble lectin 13
Reactions: Not Available
Gene Name: LGALS13
Uniprot ID: Q9UHV8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IIE secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2E
Uniprot ID: Q9NZK7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group XIIA secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G12A
Uniprot ID: Q9BZM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 85/88 kDa calcium-independent phospholipase A2
Reactions: Not Available
Gene Name: PLA2G6
Uniprot ID: O60733 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil lysophospholipase
Reactions: Not Available
Gene Name: CLC
Uniprot ID: Q05315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase A2, membrane associated
Reactions: Not Available
Gene Name: PLA2G2A
Uniprot ID: P14555 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group IID secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G2D
Uniprot ID: Q9UNK4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Dehydrogenase/reductase SDR family member 4
Reactions: Not Available
Gene Name: DHRS4
Uniprot ID: Q9BTZ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic triacylglycerol lipase
Reactions: Not Available
Gene Name: PNLIP
Uniprot ID: P16233 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hepatic triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPC
Uniprot ID: P11150 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inactive pancreatic lipase-related protein 1
Reactions: Not Available
Gene Name: PNLIPRP1
Uniprot ID: P54315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 3
Reactions: Not Available
Gene Name: PNPLA3
Uniprot ID: Q9NST1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gastric triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPF
Uniprot ID: P07098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Endothelial lipase
Reactions: Not Available
Gene Name: LIPG
Uniprot ID: Q9Y5X9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt-activated lipase
Reactions: Not Available
Gene Name: CEL
Uniprot ID: P19835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic lipase-related protein 2
Reactions: Not Available
Gene Name: PNLIPRP2
Uniprot ID: P54317 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipoprotein lipase
Reactions: Not Available
Gene Name: LPL
Uniprot ID: P06858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions: Not Available
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cocaine esterase
Reactions: Not Available
Gene Name: CES2
Uniprot ID: O00748 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cholinesterase
Reactions: Not Available
Gene Name: BCHE
Uniprot ID: P06276 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 gamma
Reactions: Not Available
Gene Name: PLA2G4C
Uniprot ID: Q9UP65 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hormone-sensitive lipase
Reactions: Not Available
Gene Name: LIPE
Uniprot ID: Q05469 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Group 3 secretory phospholipase A2
Reactions: Not Available
Gene Name: PLA2G3
Uniprot ID: Q9NZ20 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-2
Reactions: Not Available
Gene Name: ACYP2
Uniprot ID: P14621 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-1
Reactions: Not Available
Gene Name: ACYP1
Uniprot ID: P07311 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aminoacylase-1
Reactions: Not Available
Gene Name: ACY1
Uniprot ID: Q03154 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aspartoacylase
Reactions: Not Available
Gene Name: ASPA
Uniprot ID: P45381 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aspartoacylase-2
Reactions: Not Available
Gene Name: ACY3
Uniprot ID: Q96HD9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysosomal thioesterase PPT2
Reactions: Not Available
Gene Name: PPT2
Uniprot ID: Q9UMR5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acid ceramidase
Reactions: Not Available
Gene Name: ASAH1
Uniprot ID: Q13510 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Homeodomain-interacting protein kinase 1
Reactions: Not Available
Gene Name: HIPK1
Uniprot ID: Q86Z02 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Peroxisome proliferator-activated receptor gamma
Reactions: Not Available
Gene Name: PPARG
Uniprot ID: P37231 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain fatty acid transport protein 6
Reactions: Not Available
Gene Name: SLC27A6
Uniprot ID: Q9Y2P4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain fatty acid transport protein 3
Reactions: Not Available
Gene Name: SLC27A3
Uniprot ID: Q5K4L6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 4
Reactions: Not Available
Gene Name: PNPLA4
Uniprot ID: P41247 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Long-chain fatty acid transport protein 4
Reactions: Not Available
Gene Name: SLC27A4
Uniprot ID: Q6P1M0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 60 kDa lysophospholipase
Reactions: Not Available
Gene Name: ASPG
Uniprot ID: Q86U10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase B1, membrane-associated
Reactions: Not Available
Gene Name: PLB1
Uniprot ID: Q6P1J6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 2
Reactions: Not Available
Gene Name: PNPLA2
Uniprot ID: Q96AD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 delta
Reactions: Not Available
Gene Name: PLA2G4D
Uniprot ID: Q86XP0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 epsilon
Reactions: Not Available
Gene Name: PLA2G4E
Uniprot ID: Q3MJ16 Link_out
Protein Sequence: FASTA
Name: Cytosolic phospholipase A2 zeta
Reactions: Not Available
Gene Name: PLA2G4F
Uniprot ID: Q68DD2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calcium-independent phospholipase A2-gamma
Reactions: Not Available
Gene Name: PNPLA8
Uniprot ID: Q9NP80 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic phospholipase A2 beta
Reactions: Not Available
Gene Name: PLA2G4B
Uniprot ID: P0C869 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Long-chain fatty acid transport protein 1
Reactions: Not Available
Gene Name: SLC27A1
Uniprot ID: Q6PCB7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA