Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:06 UTC
HMDB IDHMDB00220
Secondary Accession NumbersNone
Metabolite Identification
Common NamePalmitic acid
DescriptionPalmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.(wikipedia) Biological Source: Occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin. Usually obtained from palm oil. Widely distributed in plants Use/Importance:. Palmitic acid is used in determination of water hardness Biological Use/Importance: Active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging. Ultrasound contrast medium (Dictionary of Organic Compounds).
Structure
Thumb
Synonyms
  1. 1-Hexyldecanoate
  2. 1-Hexyldecanoic acid
  3. 1-Pentadecanecarboxylic acid
  4. C16 fatty acid
  5. Cetylic acid
  6. Edenor C16
  7. Emersol 140
  8. Emersol 143
  9. Glycon P-45
  10. Hexadecanoate
  11. Hexadecanoic acid
  12. Hexadecanoic acid palmitic acid
  13. Hexadecoate
  14. Hexadecoic acid
  15. Hexadecylic acid
  16. Hexaectylic acid
  17. Hydrofol
  18. Hydrofol acid 1690
  19. Hystrene 8016
  20. Hystrene 9016
  21. Industrene 4516
  22. Kortacid 1698
  23. Loxiol EP 278
  24. Lunac P 95
  25. Lunac P 95KC
  26. Lunac P 98
  27. N-Hexadecanoate
  28. N-Hexadecanoic acid
  29. N-Hexadecoate
  30. N-Hexadecoic acid
  31. Palmitate
  32. Palmitic acid
  33. Palmitinate
  34. Palmitinic acid
  35. Palmitinsaeure
  36. Palmitoate
  37. Palmitoic acid
  38. PAM
  39. Pentadecanecarboxylate
  40. Pentadecanecarboxylic acid
  41. PLM
  42. Prifac 2960
  43. Prifrac 2960
  44. Pristerene 4934
  45. Univol U332
Chemical FormulaC16H32O2
Average Molecular Weight256.4241
Monoisotopic Molecular Weight256.240230268
IUPAC Namehexadecanoic acid
Traditional IUPAC Namepalmitic acid
CAS Registry Number57-10-3
SMILES
CCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)
InChI KeyIPCSVZSSVZVIGE-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)
  • Endoplasmic reticulum
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4e-05 mg/mLNot Available
LogP7.17SANGSTER (1993)
Predicted Properties
PropertyValueSource
water solubility4.070E-04 g/LALOGPS
logP7.23ALOGPS
logP6.26ChemAxon
logS-5.8ALOGPS
pKa (strongest acidic)4.95ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area37.3ChemAxon
rotatable bond count14ChemAxon
refractivity77.08ChemAxon
polarizability34.37ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Bladder
  • Epidermis
  • Fibroblasts
  • Kidney
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456Not Available
Fatty Acid Elongation In MitochondriaSMP00054map00062
Fatty acid MetabolismSMP00051map00071
Glycerolipid MetabolismSMP00039map00561
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified122 +/- 48 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified66.010 +/- 9.879 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified25.0 +/- 2.8 uMChildren (1-13 year old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified25.5 +/- 2.8 uMAdolescent (13-18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified26.7 +/- 4.4 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified63.8 +/- 0.400 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified30.49 +/- 2.64 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified18.0 +/- 12.0 uMAdult (>18 years old)Not SpecifiedNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified10.8 (2.6-32.7) umol/mmol creatinineNewborn (0-30 days old)BothNormal
UrineDetected and Quantified1.4 (0.1-7.3) umol/mmol creatinineAdolescent (13-18 years old)BothCommentNormal
UrineDetected and Quantified11 (6.0-23) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.30 +/- 0.09 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
UrineDetected and Quantified11.2 (6.0-26.1) umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified2.2 (0.8-8.2) umol/mmol creatinineChildren (1-13 year old)BothCommentNormal
UrineDetected and Quantified1.4 (0.1-3.8) umol/mmol creatinineChildren (1-13 year old)BothCommentNormal
UrineDetected and Quantified6.7(2.6-24.3) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
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 IDFDB011679
KNApSAcK IDC00030479
Chemspider ID960
KEGG Compound IDC00249
BioCyc IDCPD-8475
BiGG ID34386
Wikipedia LinkPalmitic acid
NuGOwiki LinkHMDB00220
Metagene LinkHMDB00220
METLIN ID187
PubChem Compound985
PDB IDPLM
ChEBI ID15756
References
Synthesis ReferenceXu, Yan; Ling, Li. A method for preparing conjugated linoleic acid and palmitic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
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. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  3. 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
  4. A J, Trygg J, Gullberg J, Johansson AI, Jonsson P, Antti H, Marklund SL, Moritz T: Extraction and GC/MS analysis of the human blood plasma metabolome. Anal Chem. 2005 Dec 15;77(24):8086-94. Pubmed: 16351159
  5. 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
  6. Lloyd B, Halter RJ, Kuchan MJ, Baggs GE, Ryan AS, Masor ML: Formula tolerance in postbreastfed and exclusively formula-fed infants. Pediatrics. 1999 Jan;103(1):E7. Pubmed: 9917487
  7. Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. Pubmed: 15854043
  8. Mensink RP: Nutrition in lipid disorders. Ther Umsch. 1995 Aug;52(8):509-14. Pubmed: 7676394
  9. Mesiha MS, Ponnapula S, Plakogiannis F: Oral absorption of insulin encapsulated in artificial chyles of bile salts, palmitic acid and alpha-tocopherol dispersions. Int J Pharm. 2002 Dec 5;249(1-2):1-5. Pubmed: 12433429
  10. Dubinin DM, Naidina VP, Zaloguev SN: [Evaluation of human skin function in a sealed room by a chromatographic method] Kosm Biol Aviakosm Med. 1985 Nov-Dec;19(6):69-73. Pubmed: 2868151
  11. Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. Pubmed: 12385891
  12. Otsuki T, Oku M: [A study on the effect of cortisol and progesterone on cytosolic arachidonic and palmitic acid concentrations in cultured human myometrial cells] Nippon Sanka Fujinka Gakkai Zasshi. 1995 Jun;47(6):531-8. Pubmed: 7608616
  13. Draisey TF, Gagneja GL, Thibert RJ: Pulmonary surfactant and amniotic fluid insulin. Obstet Gynecol. 1977 Aug;50(2):197-9. Pubmed: 577607
  14. Florentin E, Athias A, Lagrost L: Modulation of the activity of the human cholesteryl ester transfer protein by carboxylated derivatives. Evidence for 13-cis-retinoic acid as a potent activator of the protein's activity in plasma. Eur J Biochem. 1996 Sep 15;240(3):699-706. Pubmed: 8856073
  15. Urien S, Morin D, Tillement JP: Effect of alpha-1-acid glycoprotein, albumin and palmitic acid on the brain and salivary gland extraction of warfarin in rats. J Pharmacol Exp Ther. 1989 Feb;248(2):781-5. Pubmed: 2918479
  16. Wang J, Zhu F, Pan G: [Diagnosis of chylous ascites with oral administration of 13C-palmitic acid] Zhonghua Nei Ke Za Zhi. 1996 Jun;35(6):382-4. Pubmed: 9387625
  17. Ip MP, Draisey TF, Thibert RJ, Gagneja GL, Jasey GM: Fetal lung maturity, as assessed by gas-liquid chromatographic determination of phospholipid palmitic acid in amniotic fluid. Clin Chem. 1977 Jan;23(1):35-40. Pubmed: 832370
  18. Messner T, Erkstam UB, Gustafsson IB, Nilsson SB, Vessby B: Diet and dietary markers in Kiruna and Uppsala, Sweden--a comparison. Int J Circumpolar Health. 1997 Apr;56(1-2):21-9. Pubmed: 9300843
  19. Vessby B, Tengblad S, Lithell H: Insulin sensitivity is related to the fatty acid composition of serum lipids and skeletal muscle phospholipids in 70-year-old men. Diabetologia. 1994 Oct;37(10):1044-50. Pubmed: 7851683
  20. Liau YH, Slomiany BL, Slomiany A, Piasek A, Palmer D, Rosenthal WS: Identification of mucus glycoprotein fatty acyltransferase activity in human gastric mucosa. Digestion. 1985;32(1):57-62. Pubmed: 4018446

Only showing the first 50 proteins. There are 86 proteins in total.

Enzymes

Gene Name:
FASN
Uniprot ID:
P49327
Reactions
Hexadecanoyl-[acp] + Water unknown Acyl-carrier protein + Palmitic aciddetails
Gene Name:
LYPLA1
Uniprot ID:
O75608
Reactions
Palmitoyl-protein + Water unknown Palmitic acid + proteindetails
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:
LYPLA2
Uniprot ID:
O95372
Reactions
Palmitoyl-protein + Water unknown Palmitic acid + proteindetails
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:
BAAT
Uniprot ID:
Q14032
Reactions
hexadecanoyl-CoA + Water unknown Coenzyme A + Palmitic aciddetails
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:
ACSL4
Uniprot ID:
O60488
Reactions
Adenosine triphosphate + Palmitic acid + Coenzyme A unknown Adenosine monophosphate + hexadecanoyl-CoA + Pyrophosphatedetails
Gene Name:
ACSL1
Uniprot ID:
P33121
Reactions
Adenosine triphosphate + Palmitic acid + Coenzyme A unknown Adenosine monophosphate + hexadecanoyl-CoA + Pyrophosphatedetails
Gene Name:
ACSL6
Uniprot ID:
Q9UKU0
Reactions
Adenosine triphosphate + Palmitic acid + Coenzyme A unknown Adenosine monophosphate + hexadecanoyl-CoA + Pyrophosphatedetails
Gene Name:
ACSL5
Uniprot ID:
Q9ULC5
Reactions
Adenosine triphosphate + Palmitic acid + Coenzyme A unknown Adenosine monophosphate + hexadecanoyl-CoA + Pyrophosphatedetails
Gene Name:
ACSL3
Uniprot ID:
O95573
Reactions
Adenosine triphosphate + Palmitic acid + Coenzyme A unknown Adenosine monophosphate + hexadecanoyl-CoA + Pyrophosphatedetails
Gene Name:
ACOT7
Uniprot ID:
O00154
Reactions
hexadecanoyl-CoA + Water unknown Coenzyme A + Palmitic aciddetails
Gene Name:
ACOT2
Uniprot ID:
P49753
Reactions
hexadecanoyl-CoA + Water unknown Coenzyme A + Palmitic aciddetails
Gene Name:
ACOT4
Uniprot ID:
Q8N9L9
Reactions
hexadecanoyl-CoA + Water unknown Coenzyme A + Palmitic aciddetails
Gene Name:
ACOT8
Uniprot ID:
O14734
Gene Name:
PPT1
Uniprot ID:
P50897
Reactions
Palmitoyl-[protein] + Water unknown Palmitic acid + [protein]details
hexadecanoyl-CoA + Water unknown Coenzyme A + Palmitic aciddetails
Gene Name:
PPT2
Uniprot ID:
Q9UMR5
Reactions
hexadecanoyl-CoA + Water unknown Coenzyme A + Palmitic aciddetails
Gene Name:
ASAH1
Uniprot ID:
Q13510

Transporters

Only showing the first 50 proteins. There are 86 proteins in total.