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Identification
YMDB IDYMDB00069
NamePalmitic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPalmitic acid, also known as C16 or hexadecanoate, 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. Palmitic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Palmitic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1-hexyldecanoate
  • 1-hexyldecanoic acid
  • 1-Pentadecanecarboxylic acid
  • C16 fatty acid
  • Cetylic acid
  • Coconut oil fatty acids
  • Edenor C16
  • Hexadecanoate
  • Hexadecanoic (palmitic) acid
  • Hexadecanoic acid
  • Hexadecanoic acid (palmitic acid)
  • Hexadecanoic acid palmitic acid
  • Hexadecoate
  • Hexadecoic acid
  • Hexadecylic acid
  • Hexaectylic acid
  • Hydrofol
  • 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
  • 16:00
  • C16
  • C16:0
  • CH3-[CH2]14-COOH
  • FA 16:0
  • 1-Pentadecanecarboxylate
  • Cetylate
  • Hexadecylate
  • Hexaectylate
  • Emersol 140
  • Emersol 143
  • Glycon p-45
  • Hexadecanoate (N-C16:0)
  • Hydrofol acid 1690
  • Hystrene 8016
  • Hystrene 9016
  • Industrene 4516
  • Kortacid 1698
  • Loxiol ep 278
  • Lunac p 95
  • Lunac p 95KC
  • Lunac p 98
  • Prifac 2960
  • Prifrac 2960
  • Pristerene 4934
  • Univol u332
  • Acid, hexadecanoic
  • Acid, palmitic
  • FA(16:0)
CAS number57-10-3
WeightAverage: 256.4241
Monoisotopic: 256.240230268
InChI KeyIPCSVZSSVZVIGE-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Namehexadecanoic acid
Traditional IUPAC Namepalmitic acid
Chemical FormulaC16H32O2
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point61.8 °C
Experimental Properties
PropertyValueReference
Water Solubility4e-05 mg/mL at 25 oC [ROBB,ID (1966)]PhysProp
LogP7.17 [SANGSTER (1993)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00041 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 Area37.3 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.08 m³·mol⁻¹ChemAxon
Polarizability34.36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cell Envelope, Cytoplasm, Endoplasmic Reticulum, Extracellular, Lipid Particle, Mitochondrion, Peroxisome
Organoleptic Properties
Flavour/OdourSource
FattyFDB011679
Slightly waxyFDB011679
SMPDB Pathways
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (docosanoyl)PW002408 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (icosanoyl)PW002434 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (stearoyl)PW002435 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA)PW002404 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
Ether lipid metabolismec00565 Map00565
Fatty acid biosynthesisec00061 Map00061
Fatty acid elongation in mitochondriaec00062 Map00062
Fatty acid metabolismec00071 Map00071
SMPDB Reactions
Palmitic acid + Adenosine triphosphate + Coenzyme AAdenosine monophosphate + Pyrophosphate + Palmityl-CoA
PA(16:0/0:0) + Palmitic acidPA(16:0/16:0) + Coenzyme A
Trans-Hexa-dec-2-enoic acidPalmitic acid
Palmitic acid + Adenosine triphosphate + Coenzyme APalmityl-CoA + Adenosine monophosphate + Pyrophosphate
Palmityl-CoA + waterPalmitic acid + Coenzyme A
KEGG Reactions
myristic acid + malonyl-CoA + hydron + NADPHCarbon dioxide + NADP + water + Coenzyme A + Palmitic acid
malonyl-CoA + hydron + NADPH + Palmitic acidstearic acid + Carbon dioxide + NADP + water + Coenzyme A
hydron + malonyl-CoA + oxygen + NADPH + Palmitic acidNADP + Carbon dioxide + Coenzyme A + Oleic acid + water
Adenosine triphosphate + Coenzyme A + Palmitic acidAdenosine monophosphate + Pyrophosphate + Palmityl-CoA
water + palmitoyl-[acyl-carrier protein] ↔ acyl-carrier protein + hydron + Palmitic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Molenaar, C. M., Prange, R., Gallwitz, D. (1988). "A carboxyl-terminal cysteine residue is required for palmitic acid binding and biological activity of the ras-related yeast YPT1 protein." EMBO J 7:971-976.3042385
  • Stoops, J. K., Awad, E. S., Arslanian, M. J., Gunsberg, S., Wakil, S. J., Oliver, R. M. (1978). "Studies on the yeast fatty acid synthetase. Subunit composition and structural organization of a large multifunctional enzyme complex." J Biol Chem 253:4464-4475.350874
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
Synthesis Reference:Xu, Yan; Ling, Li. A method for preparing conjugated linoleic acid and palmitic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 5 pp.
External Links:
ResourceLink
CHEBI ID15756
HMDB IDHMDB00220
Pubchem Compound ID985
Kegg IDC00249
ChemSpider ID960
FOODB IDFDB011679
WikipediaPalmitic_acid
BioCyc IDCPD-8475

Enzymes

General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Contributes, with FAA1, to the activation of imported myristate
Gene Name:
FAA4
Uniprot ID:
P47912
Molecular weight:
77266.5
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It may supplement intracellular myristoyl-CoA pools from exogenous myristate. Preferentially acts on C12:0-C16:0 fatty acids with myristic and pentadecanic acid (C15:0) having the highest activities
Gene Name:
FAA1
Uniprot ID:
P30624
Molecular weight:
77865.79688
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. This enzyme acts preferentially on C16 and C18 fatty acids with a cis-double bond at C-9-C-10
Gene Name:
FAA3
Uniprot ID:
P39002
Molecular weight:
77946.0
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in fatty acid elongase activity
Specific function:
May be a membrane bound enzyme involved in the highly specific elongation of saturated 14-carbon fatty acids (14:0) to 16-carbon species (16:0)
Gene Name:
ELO1
Uniprot ID:
P39540
Molecular weight:
36233.60156
Reactions
Acyl-CoA + malonyl-CoA → 3-oxoacyl-CoA + CoA + CO(2).
General function:
Involved in acyltransferase activity
Specific function:
May be an acyltransferase with an altered substrate specificity that enables it to use a C-26-CoA in place of the C-16 or C-18-CoAs used by the wild-type protein
Gene Name:
SLC1
Uniprot ID:
P33333
Molecular weight:
33886.69922
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated
Gene Name:
FAA2
Uniprot ID:
P39518
Molecular weight:
83437.10156
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:
FAS1
Uniprot ID:
P07149
Molecular weight:
228689.0
Reactions
Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:
TES1
Uniprot ID:
P41903
Molecular weight:
40259.39844
Reactions
Palmitoyl-CoA + H(2)O → CoA + palmitate.
General function:
Involved in 1-acylglycerol-3-phosphate O-acyltransferas
Specific function:
Membrane-bound O-acyltransferase that mediates the incorporation of unsaturated acyl chains into the sn-2 position of phopholipids. Preferentially acylates lysophosphocholine, but also lysophosphoethanolamine and lysophosphatidylglycerol
Gene Name:
ALE1
Uniprot ID:
Q08548
Molecular weight:
72227.39844
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphocholine → CoA + 1,2-diacyl-sn-glycero-3-phosphocholine.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphoethanolamine → CoA + 1,2-diacyl-sn-glycero-3-phosphoethanolamine.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins with a strong preference for palmitoylated G-alpha proteins over other acyl substrates. Mediates the deacylation of G-alpha proteins such as GPA1 in vivo, but has weak or no activity toward palmitoylated Ras proteins. Has weak lysophospholipase activity in vitro; however such activity may not exist in vivo
Gene Name:
Not Available
Uniprot ID:
Q12354
Molecular weight:
24700.19922
Reactions
Palmitoyl-protein + H(2)O → palmitate + protein.
General function:
Involved in metabolic process
Specific function:
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium
Gene Name:
NTE1
Uniprot ID:
Q04958
Molecular weight:
187131.0
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:
TGL1
Uniprot ID:
P34163
Molecular weight:
62978.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism
Gene Name:
YEH2
Uniprot ID:
Q07950
Molecular weight:
62446.0
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
General function:
Involved in hydrolase activity, acting on ester bonds
Specific function:
Lipolytic activity towards triacylglycerols and diacylglycerols with short-chain fatty acids
Gene Name:
TGL2
Uniprot ID:
P54857
Molecular weight:
37499.89844
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
General function:
Involved in triglyceride lipase activity
Specific function:
Essential for lysis of subvacuolar cytoplasm to vacuole targeted bodies and intravacuolar autophagic bodies. Involved in the lysis of intravacuolar multivesicular body (MVB) vesicles
Gene Name:
ATG15
Uniprot ID:
P25641
Molecular weight:
58434.5
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process
Gene Name:
TGL3
Uniprot ID:
P40308
Molecular weight:
73611.79688
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL5
Uniprot ID:
Q12043
Molecular weight:
84715.10156
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL4
Uniprot ID:
P36165
Molecular weight:
102716.0
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
General function:
triglyceride metabolic process
Specific function:
Converts monoacylglycerides (MAG) to free fatty acids and glycerol. Required for efficient degradation of MAG, short-lived intermediates of glycerolipid metabolism which may also function as lipid signaling molecules. Controls inactivation of the signaling lipid N-palmitoylethanolamine (PEA).
Gene Name:
YJU3
Uniprot ID:
P28321
Molecular weight:
35562.4
Reactions
General function:
lipid particle organization
Specific function:
Acyl-CoA-dependent lysophosphatidic acid acyltransferase with preference for oleoyl-CoA. Involved in triacylglyceride homeostasis and lipid droplet formation. Involved in vacuolar protein sorting.
Gene Name:
LOA1
Uniprot ID:
Q06508
Molecular weight:
33815.635
Reactions

Transporters

General function:
Involved in catalytic activity
Specific function:
May be involved in long-chain fatty acids uptake, and thus may play a pivotal role in regulating their accessibility prior to metabolic utilization. May play an important role in uptake of these hydrophobic compounds under conditions where fatty acid synthesis is compromised
Gene Name:
FAT1
Uniprot ID:
P38225
Molecular weight:
77140.29688
Reactions