Dodecanoate (N-C12:0) (ECMDB21209) (M2MDB001617)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-07-30 14:54:57 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 17:20:53 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Dodecanoate (N-C12:0) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Dodecanoate (n-c12:0) belongs to the class of Carboxylic Acid Salts. These are ionic derivatives of carboxylic acid. (inferred from compound structure) Dodecanoic acid, also known as lauric acid is a saturated fatty acid with a 12-carbon atom chain, thus falling into the medium chain fatty acids. It is a white, powdery solid with a faint odor of bay oil or soap. (Wikipedia) In plants and bacteria like E. coli, dodecanoate is a by-product in one palmitate biosynthesis pathway. (EcoCyc) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C12H23O2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 199.3098 Monoisotopic: 199.16980498 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | POULHZVOKOAJMA-UHFFFAOYSA-M | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)/p-1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | dodecanoate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | laurate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CCCCCCCCCCCC([O-])=O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Fatty Acyls | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Fatty acids and conjugates | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Medium-chain fatty acids | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Membrane | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Coenzyme A + Dodecanoate (N-C12:0) + Hydrogen ion > Adenosine monophosphate + Lauroyl-CoA + Hydrogen ion + Pyrophosphate acyl carrier protein + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + Dodecanoyl-ACP (n-C12:0ACP) + Pyrophosphate Dodecanoyl-ACP (n-C12:0ACP) + Water > acyl carrier protein + Dodecanoate (N-C12:0) + Hydrogen ion Lauroyl-CoA + Water > Coenzyme A + Dodecanoate (N-C12:0) + Hydrogen ion 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion 1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion 1-Dodecanoyl-sn-glycerol 3-phosphate + Water > Dodecanoate (N-C12:0) + Glycerol 3-phosphate + Hydrogen ion Dodecanoly-phosphate (n-C12:0) + Water > Dodecanoate (N-C12:0) +2 Hydrogen ion + Phosphate 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PE(14:0/14:0) + Pyrophosphate 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Adenosine triphosphate + Dodecanoate (N-C12:0) > Adenosine monophosphate + PG(12:0/12:0) + Pyrophosphate Water + PA(16:0/16:0) > 1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0) + Hydrogen ion Water + PA(16:0/16:0) > 2-dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0) Water + PE(14:0/14:0) > 1-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion Water + PE(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion Water + PG(12:0/12:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion Water + PG(12:0/12:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Dodecanoate (N-C12:0) + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoethanolamine (N-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerylphosphorylethanolamine + Hydrogen ion 2-Acyl-sn-glycero-3-phosphoglycerol (n-C12:0) + Water > Dodecanoate (N-C12:0) + Glycerophosphoglycerol + Hydrogen ion 2-dodecanoyl-sn-glycerol 3-phosphate + Water > Dodecanoate (N-C12:0) + Glycerol 3-phosphate +2 Hydrogen ion | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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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:
- 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