| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 1-Tridecanecarboxylate
- 1-Tridecanecarboxylic acid
- Crodacid
- Myristate
- Myristic acid
- Myristic acid pure
- Myristoate
- Myristoic acid
- N-Tetradecan-1-oate
- N-Tetradecan-1-oic acid
- N-Tetradecanoate
- N-Tetradecanoic acid
- Tetradecanoate
- Tetradecanoic (Myristic) acid
- 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 |
|
| Direct Parent |
Straight Chain Fatty Acids |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| 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 |
|
| Spectra |
|
|
| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane (predicted from logP)
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
|
| Tissue Location |
- Epidermis
- Prostate
- Adipose Tissue
- Spleen
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| Pathways |
| Name |
SMPDB Link |
KEGG Link |
| Fatty Acid Biosynthesis |
SMP00456
|
Not Available
|
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| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
25.0 (8.0-70.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
3.0 +/- 1.3 uM |
Children (1-13 year old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
7.16 +/- 3 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
9.3 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
15.464 +/- 4.024 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
2.7 +/- 1.5 uM |
Adolescent (13-18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
2.1 +/- 0.9 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
6.06 +/- 0.069 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
5.0 +/- 5.0 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.06 +/- 0.03 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
Not Available |
| Associated Disorders and Diseases |
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB002890 |
| KNApSAcK ID |
C00001228  |
| Chemspider ID |
10539  |
| KEGG Compound ID |
C06424  |
| BioCyc ID |
Not Available |
| BiGG ID |
215851  |
| Wikipedia Link |
Myristic acid  |
| NuGOwiki Link |
HMDB00806  |
| Metagene Link |
HMDB00806  |
| METLIN ID |
196  |
| PubChem Compound |
11005  |
| PDB ID |
MYR  |
| ChEBI ID |
28875  |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Matsubara M: [Structures and molecular recognition of MARCKS family proteins] Seikagaku. 2005 Jan;77(1):50-5.
Pubmed: 15770953
- 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
- 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
- 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
- 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
- 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
- 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
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| Enzymes |
| Name: |
Fatty acid synthase
|
| Reactions: |
- a (3R)-3-hydroxypalmitoyl-[acyl-carrier protein] = a hexadec-2-enoyl-[acyl-carrier protein] + H2O [RN:R04462]
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| Gene Name: |
FASN |
| Uniprot ID: |
P49327  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Cytosolic phospholipase A2
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| Reactions: |
- 2-lysophosphatidylcholine + H2O = glycerophosphocholine + a carboxylate [RN:R07291]
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| Gene Name: |
PLA2G4A |
| Uniprot ID: |
P47712  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Phospholipase A2
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| Reactions: |
- phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
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| Gene Name: |
PLA2G1B |
| Uniprot ID: |
P04054  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Endothelial lipase
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| Reactions: |
- triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
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| Gene Name: |
LIPG |
| Uniprot ID: |
Q9Y5X9  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lipoprotein lipase
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| Reactions: |
- triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
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| Gene Name: |
LPL |
| Uniprot ID: |
P06858  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Carboxylesterase 2
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| Reactions: |
- a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
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| Gene Name: |
CES2 |
| Uniprot ID: |
O00748  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Cholinesterase
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| Reactions: |
- an acylcholine + H2O = choline + a carboxylate [RN:R01029]
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| Gene Name: |
BCHE |
| Uniprot ID: |
P06276  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
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| Name: |
Hormone-sensitive lipase
|
| Reactions: |
- (1) diacylglycerol + H2O = monoacylglycerol + a carboxylate [RN:R05209]
- (2) triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
- (3) monoacylglycerol + H2O = glycerol + a carboxylate [RN:R07293]
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| Gene Name: |
LIPE |
| Uniprot ID: |
Q05469  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acylphosphatase-2
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| Reactions: |
- an acylphosphate + H2O = a carboxylate + phosphate [RN:R00539]
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| Gene Name: |
ACYP2 |
| Uniprot ID: |
P14621  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Acylphosphatase-1
|
| Reactions: |
- an acylphosphate + H2O = a carboxylate + phosphate [RN:R00539]
|
| Gene Name: |
ACYP1 |
| Uniprot ID: |
P07311  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Aminoacylase-1
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| Reactions: |
- an N-acyl-L-amino acid + H2O = a carboxylate + an L-amino acid [RN:R01263]
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| Gene Name: |
ACY1 |
| Uniprot ID: |
Q03154  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Aspartoacylase
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| Reactions: |
- N-acyl-L-aspartate + H2O = a carboxylate + L-aspartate [RN:R00546]
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| Gene Name: |
ASPA |
| Uniprot ID: |
P45381  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acid ceramidase
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ASAH1 |
| Uniprot ID: |
Q13510  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alkaline ceramidase 2
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ACER2 |
| Uniprot ID: |
Q5QJU3  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Neutral ceramidase
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ASAH2 |
| Uniprot ID: |
Q9NR71  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Carboxylesterase 7
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| Reactions: |
- a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
|
| Gene Name: |
CES7 |
| Uniprot ID: |
Q6NT32  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
|
| Name: |
Alkaline ceramidase 1
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| Reactions: |
- N-acylsphingosine + H2O = a carboxylate + sphingosine [RN:R01493]
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| Gene Name: |
ACER1 |
| Uniprot ID: |
Q8TDN7  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Carboxylesterase 3
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| Reactions: |
- a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
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| Gene Name: |
CES3 |
| Uniprot ID: |
Q6UWW8  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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