General Information of MET (ID: META00088)
Name Palmitic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-Hexyldecanoate; 1-Hexyldecanoic acid; 1-Pentadecanecarboxylate; 1-Pentadecanecarboxylic acid; 16:00; Acid, hexadecanoic; Acid, palmitic; C16; C16 Fatty acid; C16:0; CH3-[CH2]14-COOH; Cetylate; Cetylic acid; Edenor C16; Emersol 140; Emersol 143; FA 16:0; FA(16:0); Glycon p-45; Hexadecanoate; Hexadecanoate (N-C16:0); Hexadecanoic acid; 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; PAM; PLM; Palmitate; Palmitinate; Palmitinic acid; Palmitinsaeure; Palmitoate; Palmitoic acid; Pentadecanecarboxylate; Pentadecanecarboxylic acid; Prifac 2960; Prifrac 2960; Pristerene 4934; Univol u332
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Fatty acyls;Food;Drug;Agricultural Chemicals;Toxins/Pollutant;Cosmetic;Food additives;TCM Ingredients;Microbial
Structure Type   Fatty acids and conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acids and conjugates
PubChem CID
985
HMDB ID
HMDB0000220
Formula
C16H32O2
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00249
DrugBank ID
DB03796
ChEBI ID
15756
FooDB ID
FDB031084
ChemSpider ID
960
METLIN ID
187
Physicochemical Properties Molecular Weight 256.42 Topological Polar Surface Area 37.3
XlogP 6.4 Complexity 178
Heavy Atom Count 18 Rotatable Bond Count 14
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Function
Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21-30% (molar) of human depot fat , and it is a major, but highly variable, lipid component of human breast milk. Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid. Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Free fatty acid receptor 1 (FFAR1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Palmitic acid addition (1 hours)
                      Induced Change FFAR1 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Diabetic acidosis [ICD-11: 5A22]
                      Details It is reported that palmitic acid addition causes the increase of FFAR1 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Transcription factor (TF)
            Hypoxia-inducible factor 1-alpha (HIF1A) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of HIF1A
                      Induced Change Palmitic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockout of HIF1A leads to the increase of palmitic acid levels compared with control group.
      Transferases (EC 2)
            Deacetylase sirtuin-5 (SIRT5) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of Sirt5
                      Induced Change Palmitic acid concentration: increase (FC = 1.16)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Sirt5 leads to the increase of palmitic acid levels compared with control group.
References
1 Deorphanization of GPR109B as a receptor for the beta-oxidation intermediate 3-OH-octanoic acid and its role in the regulation of lipolysis. J Biol Chem. 2009 Aug 14;284(33):21928-21933.
2 Hypoxia induces a lipogenic cancer cell phenotype via HIF1-dependent and -independent pathways. Oncotarget. 2015 Feb 10;6(4):1920-41.
3 Metabolomics Based Identification of SIRT5 and Protein Kinase C Epsilon Regulated Pathways in Brain. Front Neurosci. 2018 Jan 30;12:32.

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