Palmitic acid (ECMDB00220) (M2MDB000091)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:24:03 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:07 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C16H32O2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 256.4241 Monoisotopic: 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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 61.8 °C | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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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) Hydrogen ion + Palmitic acid + KDO2-Lipid A > Water + Hepta-acylated KDO2-lipid A 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 Adenosine triphosphate + Coenzyme A + Hydrogen ion + Palmitic acid > Adenosine monophosphate + Palmityl-CoA + Pyrophosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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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) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Lipid transport and metabolism
- Specific function:
- 2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
- Gene Name:
- pldB
- Uniprot ID:
- P07000
- Molecular weight:
- 38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate. |
- General function:
- Involved in phospholipase activity
- Specific function:
- Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
- Gene Name:
- pldA
- Uniprot ID:
- P0A921
- Molecular weight:
- 33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate. |
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate. |
- General function:
- Involved in acylphosphatase activity
- Specific function:
- An acylphosphate + H(2)O = a carboxylate + phosphate
- Gene Name:
- yccX
- Uniprot ID:
- P0AB65
- Molecular weight:
- 10300
Reactions
An acylphosphate + H(2)O = a carboxylate + phosphate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
- Gene Name:
- tesA
- Uniprot ID:
- P0ADA1
- Molecular weight:
- 23622
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate. |
- General function:
- Involved in [acyl-carrier-protein] phosphodiesterase activity
- Specific function:
- Converts holo-ACP to apo-ACP by hydrolytic cleavage of the phosphopantetheine prosthetic group from ACP
- Gene Name:
- acpH
- Uniprot ID:
- P21515
- Molecular weight:
- 22961
Reactions
Holo-[acyl-carrier-protein] + H(2)O = 4'-phosphopantetheine + apo-[acyl-carrier-protein]. |
- General function:
- Involved in transferase activity, transferring acyl groups
- Specific function:
- Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
- Gene Name:
- aas
- Uniprot ID:
- P31119
- Molecular weight:
- 80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine. |
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein]. |
- 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
- Uniprot ID:
- P69451
- Molecular weight:
- 62332
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA. |
- General function:
- Not Available
- Specific function:
- Not known; overproduction leads to camphor resistance and chromosome condensation
- Gene Name:
- crcA
- Uniprot ID:
- P37001
- Molecular weight:
- 21770
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the esterification, concomitant with transport, of exogenous fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It has a low activity on medium or long chain fatty acids and is maximally active on C6 and C8 substrates
- Gene Name:
- fadK
- Uniprot ID:
- P38135
- Molecular weight:
- 60773
Reactions
ATP + a short-chain carboxylic 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
- Uniprot ID:
- P0AGG2
- Molecular weight:
- 31966
- General function:
- Involved in fatty acid biosynthetic process
- Specific function:
- Carrier of the growing fatty acid chain in fatty acid biosynthesis
- Gene Name:
- acpP
- Uniprot ID:
- P0A6A8
- Molecular weight:
- 8640
Transporters
- General function:
- Lipid transport and metabolism
- Specific function:
- Involved in translocation of long-chain fatty acids across the outer membrane. It is a receptor for the bacteriophage T2. FadL may form a specific channel
- Gene Name:
- fadL
- Uniprot ID:
- P10384
- Molecular weight:
- 48541