Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000091
Identification
Name: Palmitic acid
Description:Palmitic acid, or hexadecanoic acid is a saturated fatty acids. Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-CoA to malonyl-CoA which is used to add to the growing acyl chain, thus preventing further palmitate generation. (Wikipedia)
Structure
Thumb
Synonyms:
  • 1-Hexyldecanoate
  • 1-Hexyldecanoic acid
  • 1-Pentadecanecarboxylate
  • 1-Pentadecanecarboxylic acid
  • C16 fatty acid
  • Cetylate
  • Cetylic acid
  • Edenor C16
  • Emersol 140
  • Emersol 143
  • Glycon P-45
  • Hexadecanoate
  • Hexadecanoate (N-C16:0)
  • Hexadecanoate palmitate
  • Hexadecanoate palmitic acid
  • Hexadecanoic acid
  • Hexadecanoic acid (N-C16:0)
  • Hexadecanoic acid palmitic acid
  • Hexadecoate
  • Hexadecoic acid
  • Hexadecylate
  • Hexadecylic acid
  • Hexaectylate
  • Hexaectylic acid
  • Hydrofol
  • Hydrofol acid 1690
  • Hystrene 8016
  • Hystrene 9016
  • Industrene 4516
  • Kortacid 1698
  • Loxiol EP 278
  • Lunac P 95
  • Lunac P 95KC
  • Lunac P 98
  • N-Hexadecanoate
  • N-Hexadecanoic acid
  • N-Hexadecoate
  • N-Hexadecoic acid
  • Palmitate
  • Palmitic acid
  • Palmitinate
  • Palmitinic acid
  • Palmitinsaeure
  • Palmitoate
  • Palmitoic acid
  • PAM
  • Pentadecanecarboxylate
  • Pentadecanecarboxylic acid
  • PLM
  • Prifac 2960
  • Prifrac 2960
  • Pristerene 4934
  • Univol U332
Chemical Formula: C16H32O2
Average Molecular Weight: 256.4241
Monoisotopic Molecular Weight: 256.240230268
InChI Key: IPCSVZSSVZVIGE-UHFFFAOYSA-N
InChI: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)
CAS number: 57-10-3
IUPAC Name:hexadecanoic acid
Traditional IUPAC Name: palmitic acid
SMILES:CCCCCCCCCCCCCCCC(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Long-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 61.8 °C
Experimental Properties:
PropertyValueSource
Water Solubility:0.04 mg/L [ROBB.ID (1966)]PhysProp
LogP:7.17 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000407 mg/mLALOGPS
logP7.23ALOGPS
logP6.26ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.08 m3·mol-1ChemAxon
Polarizability34.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Adenosine triphosphate + Coenzyme A + Hydrogen ion + Palmitic acid > Adenosine monophosphate + Hydrogen ion + Palmityl-CoA + Pyrophosphate
acyl carrier protein + Adenosine triphosphate + Palmitic acid > Adenosine monophosphate + Palmitoyl-ACP (n-C16:0ACP) + Pyrophosphate
Water + Palmitoyl-ACP (n-C16:0ACP) > acyl carrier protein + Hydrogen ion + Palmitic acid
Water + Palmityl-CoA > Coenzyme A + Hydrogen ion + Palmitic acid
1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid
1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid
1-hexadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate + Hydrogen ion + Palmitic acid
core oligosaccharide lipid A + Hydrogen ion + Palmitic acid > Water + hepta-acylated core oligosaccharide lipid A (E. coli)
Water + Hexadecanoyl-phosphate (n-C16:0) >2 Hydrogen ion + Palmitic acid + Phosphate
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Adenosine triphosphate + Palmitic acid > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Adenosine triphosphate + Palmitic acid > Adenosine monophosphate + PG(16:0/16:0) + Pyrophosphate
Water + PA(16:0/16:0) > 1-hexadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Palmitic acid
Water + PA(16:0/16:0) > 2-hexadecanoyl-sn-glycerol 3-phosphate + Palmitic acid
Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Hydrogen ion + Palmitic acid
Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Hydrogen ion + Palmitic acid
Water + PG(16:0/16:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Hydrogen ion + Palmitic acid
Water + PG(16:0/16:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Hydrogen ion + Palmitic acid
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C16:0) + Water > Glycerylphosphorylethanolamine + Hydrogen ion + Palmitic acid
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid
2-hexadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 Hydrogen ion + Palmitic acid
Adenosine triphosphate + Palmitic acid + Coenzyme A <> Adenosine monophosphate + Palmityl-CoA + Pyrophosphate
Palmitic acid + Adenosine triphosphate + Coenzyme A > Palmityl-CoA + Adenosine monophosphate + Pyrophosphate
Palmitic acid + Coenzyme A + Adenosine triphosphate > Adenosine monophosphate + Palmityl-CoA
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-014i-0901000000-51ee83f9462d25fa4045View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0100-9700000000-3d8b6cf4736afa482b57View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2901000000-fb423e89a78708021db1View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0090000000-39c3a0e17432781e9760View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0090000000-8ec1a6953701fc22ce27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0fba-9200000000-23c995bf81d5ef609489View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0abc-9110000000-12f1884d67998fb924a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-26bb4965a56ab0e82b49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rj-5790000000-251700f3edf9a5af04cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-5b75a67e276017f221b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-26bb4965a56ab0e82b49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rj-5790000000-251700f3edf9a5af04cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-5b75a67e276017f221b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-e4a4200bd25f8fa480ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1090000000-768a48058fc0a2d7a877View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-c9714c7ffdc804bf9323View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-e4a4200bd25f8fa480ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bti-1090000000-768a48058fc0a2d7a877View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-c9714c7ffdc804bf9323View in MoNA
MSMass Spectrum (Electron Ionization)splash10-06xx-9100000000-7ac9cd088cb9cb9f7560View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • 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
  • Draisey TF, Gagneja GL, Thibert RJ: Pulmonary surfactant and amniotic fluid insulin. Obstet Gynecol. 1977 Aug;50(2):197-9. Pubmed: 577607
  • 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
  • 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
  • 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
  • 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
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • Mensink RP: Nutrition in lipid disorders. Ther Umsch. 1995 Aug;52(8):509-14. Pubmed: 7676394
  • 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
  • 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
  • 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
  • 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
  • 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
  • Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Xu, 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) Download (PDF)
External Links:
ResourceLink
CHEBI ID15756
HMDB IDHMDB00220
Pubchem Compound ID985
Kegg IDC00249
ChemSpider ID960
WikipediaPalmitic acid
BioCyc IDPALMITATE
EcoCyc IDPALMITATE
Ligand ExpoPLM

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Locus Tag:
PA5089
Molecular weight:
83.4 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Locus Tag:
PA2856
Molecular weight:
21 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:
fadD
Locus Tag:
PA3299
Molecular weight:
61.7 kDa
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in acyl-CoA hydrolase activity
Specific function:
Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:
tesB
Locus Tag:
PA3942
Molecular weight:
32.9 kDa
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Locus Tag:
PA2966
Molecular weight:
8.7 kDa

Transporters