P. aeruginosa Metabolome Database: Palmitic acid (PAMDB000091)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000091

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

🔍MOL SDF PDB SMILES InChI View Structure

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 Description

This 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 Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty 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

long-chain fatty acid (CHEBI:15756 )
straight-chain saturated fatty acid (CHEBI:15756 )
Straight chain fatty acids (C00249 )
Saturated fatty acids (C00249 )
Straight chain fatty acids (LMFA01010001 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

61.8 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	0.04 mg/L [ROBB.ID (1966)]	PhysProp
LogP:	7.17 [SANGSTER (1993)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.000407 mg/mL	ALOGPS
logP	7.23	ALOGPS
logP	6.26	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	77.08 m³·mol^-1	ChemAxon
Polarizability	34.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

Pathways:

Biosynthesis of unsaturated fatty acids pae01040
Fatty acid biosynthesis pae00061
Fatty acid metabolism pae00071

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-014i-0901000000-51ee83f9462d25fa4045	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0100-9700000000-3d8b6cf4736afa482b57	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0159-2901000000-fb423e89a78708021db1	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-0090000000-39c3a0e17432781e9760	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0090000000-8ec1a6953701fc22ce27	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0fba-9200000000-23c995bf81d5ef609489	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0abc-9110000000-12f1884d67998fb924a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-26bb4965a56ab0e82b49	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06rj-5790000000-251700f3edf9a5af04cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-5b75a67e276017f221b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-e4a4200bd25f8fa480cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1090000000-768a48058fc0a2d7a877	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9320000000-c9714c7ffdc804bf9323	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-06xx-9100000000-7ac9cd088cb9cb9f7560	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

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
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)

Links

External Links:

Resource	Link
CHEBI ID	15756
HMDB ID	HMDB00220
Pubchem Compound ID	985
Kegg ID	C00249
ChemSpider ID	960
Wikipedia	Palmitic acid
BioCyc ID	PALMITATE
EcoCyc ID	PALMITATE
Ligand Expo	PLM

Enzymes

Protein Details

• Lysophospholipase L2

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.

Protein Details

• Acyl-CoA thioesterase I

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.

Protein Details

• Long-chain-fatty-acid--CoA ligase

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.

Protein Details

• Acyl-CoA thioesterase 2

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

Protein Details

• Acyl carrier protein

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

Palmitic acid (PAMDB000091)

Structure for Palmitic acid (PAMDB000091)

Enzymes

Reactions

Reactions

Reactions

Transporters