2.0 2012-07-30 14:54:57 -0600 2015-06-03 17:20:53 -0600 ECMDB21209 M2MDB001617 Dodecanoate (N-C12:0) 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) <i>n</i>-dodecanoic acid Dodecanoate Dodecanoic acid Dodecanoic acid (N-C12:0) Laate Laic acid Laurate Lauric acid N-Dodecanoate N-Dodecanoic acid Tin II 2-ethylhexanoate Tin II 2-ethylhexanoic acid C12H23O2 199.3098 199.16980498 dodecanoate laurate CCCCCCCCCCCC([O-])=O 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 POULHZVOKOAJMA-UHFFFAOYSA-M Membrane logp 5.24 ALOGPS logs -4.72 ALOGPS solubility 4.14e-03 g/l ALOGPS logp 4.48 ChemAxon pka_strongest_acidic 4.95 ChemAxon iupac dodecanoate ChemAxon average_mass 199.3098 ChemAxon mono_mass 199.16980498 ChemAxon smiles CCCCCCCCCCCC([O-])=O ChemAxon formula C12H23O2 ChemAxon 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 ChemAxon inchikey POULHZVOKOAJMA-UHFFFAOYSA-M ChemAxon polar_surface_area 40.13 ChemAxon refractivity 69.52 ChemAxon polarizability 25.37 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon palmitate biosynthesis 2 Palmitate is synthesized by stepwise condensation of C2 units to a growing acyl chain. Each elongation cycle results in the addition of two carbons to the acyl chain, and consists of four separate reactions. The pathway starts with acetyl-CoA interacting with hydrogen carbonate through an ATP driven acetyl-CoA carboxylase resulting in a phosphate, an ADP , a hydrogen ion and a malonyl-CoA. The latter compound interacts with a holo-[acp] through a malonyl-CoA-ACP transacylase resulting in a CoA and a malonyl-[acp]. This compound interacts with hydrogen ion, acetyl-CoA through a KASIII resulting in a CoA, carbon dioxide and an acetoacetyl-[acp]. The latter compound interacts with a hydrogen ion through a NADPH driven 3-oxoacyl-[acyl-carrier-protein] reductase resulting in an NADP and a (R) 3-Hydroxybutanoyl-[acp](1). This compound is then dehydrated by a 3-hydroxyacyl-[acyl-carrier-protein] dehydratase resulting in the release of water and a crotonyl-[acp](2). The crotonyl-[acp] interacts with a hydrogen ion through a NADH enoyl-[acyl-carrier-protein] reductase(NAD) resulting in NAD and a butyryl-[acp](3). The butyryl-[acp] interacts with a hydrogen ion, a malonyl-[acp] through a KASI resulting in a holo-[acp],carbon dioxide and a 3-oxo-hexanoyl-[acp](4). The 3-oxo-hexanoyl-[acp] interacts with a hydrogen ion through a NADPH driven 3-oxoacyl-[acyl-carrier-protein] reductase resulting in an NADP and a (R) 3-Hydroxyhexanoyl-[acp](1). This compound is then dehydrated by a 3-hydroxyacyl-[acyl-carrier-protein] dehydratase resulting in the release of water and a trans hex-2-enoyl-[acp](2). The trans hex-2-enoyl-[acp] interacts with a hydrogen ion through a NADH enoyl-[acyl-carrier-protein] reductase(NAD) resulting in NAD and a hexanoyl-[acp](3). The hexanoyl-[acp] interacts with a hydrogen ion, a malonyl-[acp] through a KASI resulting in a holo-[acp],carbon dioxide and a 3-oxo-octanoyl-[acp](4). The 3-oxo-octanoyl-[acp] interacts with a hydrogen ion through a NADPH driven 3-oxoacyl-[acyl-carrier-protein] reductase resulting in an NADP and a (R) 3-Hydroxyoctanoyl-[acp](1). This compound is then dehydrated by a 3-hydroxyacyl-[acyl-carrier-protein] dehydratase resulting in the release of water and a trans oct-2-enoyl-[acp](2). The trans oct-2-enoyl-[acp] interacts with a hydrogen ion through a NADH enoyl-[acyl-carrier-protein] reductase(NAD) resulting in NAD and a octanoyl-[acp](3). The octanoyl-[acp] interacts with a hydrogen ion, a malonyl-[acp] through a KASI resulting in a holo-[acp],carbon dioxide and a 3-oxo-decanoyl-[acp](4). The 3-oxo-decanoyl-[acp] interacts with a hydrogen ion through a NADPH driven 3-oxoacyl-[acyl-carrier-protein] reductase resulting in an NADP and a (R) 3-Hydroxydecanoyl-[acp](1). This compound is then dehydrated by a 3-hydroxyacyl-[acyl-carrier-protein] dehydratase resulting in the release of water and a trans-delta2-decenoyl-[acp](2). The a trans-delta2-decenoyl-[acp] interacts with a hydrogen ion through a NADH enoyl-[acyl-carrier-protein] reductase(NAD) resulting in NAD and a decanoyl-[acp](3). The decanoyl-[acp] interacts with a malonyl-[acp] through a KASI resulting in a holo-[acp],carbon dioxide and a 3-oxo-dodecanoyl-[acp](4). The 3-oxo-dodecanoyl-[acp ]interacts with a hydrogen ion through a NADPH driven 3-oxoacyl-[acyl-carrier-protein] reductase resulting in an NADP and a (R) 3-Hydroxydodecanoyl-[acp](1). This compound is then dehydrated by a 3-hydroxyacyl-[acyl-carrier-protein] dehydratase resulting in the release of water and a trans dodec-2-enoyl-[acp](2). The trans dodec-2-enoyl-[acp] interacts with a hydrogen ion through a NADH enoyl-[acyl-carrier-protein] reductase(NAD) resulting in NAD and a dodecanoyl-[acp](3). This compound can either react with water spontaneously resulting in a hydrogen ion, a holo-[acp] and a dodecanoic acid or it interacts with a hydrogen ion, a malonyl-[acp] through a KASI resulting in a holo-[acp],carbon dioxide and a 3-oxo-myristoyl-[acp](4). The 3-oxo-myristoyl-[acp] interacts with a hydrogen ion through a NADPH driven 3-oxoacyl-[acyl-carrier-protein] reductase resulting in an NADP and a (3R) 3-Hydroxymyristoyl-[acp](1). This compound is then dehydrated by a 3-hydroxyacyl-[acyl-carrier-protein] dehydratase resulting in the release of water and a trans tetradec-2-enoyl-[acp](2). This compound interacts with a hydrogen ion, through a NADH-driven KASI resulting in a NAD and a myristoyl-[acp]. Myristoyl-[acp] with a hydrogen ion, a malonyl-[acp] through a KASI resulting in a holo-[acp],carbon dioxide and a 3-oxo-palmitoyl-[acp](4). The 3-oxo-palmitoyl-[acp] interacts with a hydrogen ion through a NADPH driven 3-oxoacyl-[acyl-carrier-protein] reductase resulting in an NADP and a (3R) 3-Hydroxypalmitoyl-[acp](1). This compound is then dehydrated by a 3-hydroxyacyl-[acyl-carrier-protein] dehydratase resulting in the release of water and a trans hexadecenoyl-[acp](2). The trans hexadecenoyl-[acp] interacts with a hydrogen ion through a NADH enoyl-[acyl-carrier-protein] reductase(NAD) resulting in NAD and a palmitoyl-[acp](3). Palmitoyl then reacts with water spontaneously resulting in a hydrogen ion, a holo-[acp] and palmitic acid. No integral membrane protein required for long chain fatty acid uptake has been identified in E. coli. The transport of long chain fatty acids across the cytoplasmic membrane is dependent on fatty acyl-CoA synthetase. An energised membrane is necessary for fatty acid transport and it has been suggested that uncharged fatty acids flip across the inner membrane by diffusion. PW002044 Metabolic palmitate biosynthesis II (bacteria and plants) PWY-5971 Specdb::NmrOneD 269818 Specdb::NmrOneD 269819 Specdb::NmrOneD 269820 Specdb::NmrOneD 269821 Specdb::NmrOneD 269822 Specdb::NmrOneD 269823 Specdb::NmrOneD 269824 Specdb::NmrOneD 269825 Specdb::NmrOneD 269826 Specdb::NmrOneD 269827 Specdb::NmrOneD 269828 Specdb::NmrOneD 269829 Specdb::NmrOneD 269830 Specdb::NmrOneD 269831 Specdb::NmrOneD 269832 Specdb::NmrOneD 269833 Specdb::NmrOneD 269834 Specdb::NmrOneD 269835 Specdb::NmrOneD 269836 Specdb::NmrOneD 269837 Specdb::MsMs 23552 Specdb::MsMs 23553 Specdb::MsMs 23554 Specdb::MsMs 30350 Specdb::MsMs 30351 Specdb::MsMs 30352 4149208 3361474 C02679 18262 DODECANOATE 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. 21097882 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 Lysophospholipase L2 P07000 PLDB_ECOLI pldB http://ecmdb.ca/proteins/P07000.xml Phospholipase A1 P0A921 PA1_ECOLI pldA http://ecmdb.ca/proteins/P0A921.xml Acylphosphatase P0AB65 ACYP_ECOLI yccX http://ecmdb.ca/proteins/P0AB65.xml Acyl-CoA thioesterase I P0ADA1 TESA_ECOLI tesA http://ecmdb.ca/proteins/P0ADA1.xml Acyl carrier protein phosphodiesterase P21515 ACPH_ECOLI acpH http://ecmdb.ca/proteins/P21515.xml Bifunctional protein aas P31119 AAS_ECOLI aas http://ecmdb.ca/proteins/P31119.xml Long-chain-fatty-acid--CoA ligase P69451 LCFA_ECOLI fadD http://ecmdb.ca/proteins/P69451.xml Short-chain-fatty-acid--CoA ligase P38135 FADK_ECOLI fadK http://ecmdb.ca/proteins/P38135.xml Acyl-CoA thioesterase 2 P0AGG2 TESB_ECOLI tesB http://ecmdb.ca/proteins/P0AGG2.xml Acyl carrier protein P0A6A8 ACP_ECOLI acpP http://ecmdb.ca/proteins/P0A6A8.xml Long-chain fatty acid transport protein P10384 FADL_ECOLI fadL http://ecmdb.ca/proteins/P10384.xml 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