2.0 2015-06-08 15:09:31 -0600 2015-08-05 16:22:05 -0600 ECMDB23862 M2MDB005464 3-Oxoacyl-[acyl-carrier protein] An acyl-[acyl-carrier protein] where the acyl group is substituted at position 3 by an oxo group 2-dehydro-3-Deoxy-L-arabinonate 2-dehydro-3-Deoxy-L-arabinonic acid 2-dehydro-3-Deoxy-L-pentonate 2-dehydro-3-Deoxy-L-pentonic acid 3-Deoxy-L-glycero-pentulosonate 3-Deoxy-L-glycero-pentulosonic acid C5H8O5 148.114 148.037173358 (4R)-4,5-dihydroxy-2-oxopentanoic acid 3-deoxy-L-pent-2-ulosonic acid OC[C@H](O)CC(=O)C(O)=O InChI=1S/C5H8O5/c6-2-3(7)1-4(8)5(9)10/h3,6-7H,1-2H2,(H,9,10)/t3-/m1/s1 UQIGQRSJIKIPKZ-GSVOUGTGSA-N logp -1.62 ALOGPS logs 0.14 ALOGPS solubility 2.05e+02 g/l ALOGPS logp -1.1 ChemAxon pka_strongest_acidic 2.91 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (4R)-4,5-dihydroxy-2-oxopentanoic acid ChemAxon average_mass 148.114 ChemAxon mono_mass 148.037173358 ChemAxon smiles OC[C@H](O)CC(=O)C(O)=O ChemAxon formula C5H8O5 ChemAxon inchi InChI=1S/C5H8O5/c6-2-3(7)1-4(8)5(9)10/h3,6-7H,1-2H2,(H,9,10)/t3-/m1/s1 ChemAxon inchikey UQIGQRSJIKIPKZ-GSVOUGTGSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 30.35 ChemAxon polarizability 12.85 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Biotin metabolism Biotin (vitamin H or vitamin B7) is the essential cofactor of biotin-dependent carboxylases, such as pyruvate carboxylase and acetyl-CoA carboxylase.In E. coli and many organisms, pimelate thioester is derived from malonyl-ACP. The pathway starts with a malonyl-[acp] interacting with S-adenosylmethionine through a biotin synthesis protein BioC resulting in a S-adenosylhomocysteine and a malonyl-[acp] methyl ester. The latter compound is then involved in the synthesis of a 3-ketoglutaryl-[acp] methyl ester through a 3-oxoacyl-[acyl-carrier-protein] synthase. The compound 3-ketoglutaryl-[acp] methyl ester is reduced by a NADPH mediated 3-oxoacyl-[acyl-carrier-protein] reductase resulting in a 3R-hydroxyglutaryl-[acp] methyl ester. This compound is then dehydrated through ad (3R)-hydroxymyristoyl-[acp] dehydratase producing a enoylglutaryl-[acp] methyl ester. This compound is then reduced through a NADPH mediated enoyl-acp-reductase [NADH] resulting in a glutaryl-[acp] methyl ester. This compound interacts with a malonyl-[acp] through a 3-oxoacyl-[acp] synthase 2 resulting in a 3-ketopimeloyl [acp] methyl ester. This compound is then reduced through a NADPH 3-oxoacyl [acp] reductase producing a 3-hydroxypimeloyl-[acp] methyl ester and then dehydrated by (3R)-hydroxymyristoyl-[acp] dehydratase to produce a enoylpimeloyl-[acp] methyl ester. This compound is then reduced by a NADPH dependent enoyl-[acp]reductase resulting in a pimeloyl-[acp] methyl ester. This compound then reacts with water through a carboxylesterase resulting in a pimeloyl-[acp] and a methanol. The pimeloyl-acp reacts with L-alanine through a 8-amino-7-oxononanoate synthase resulting in 8-amino-7-oxononanoate which in turn reacts with S-adenosylmethionine through a 7,8 diaminonanoate transaminase resulting in a S-adenosyl-4-methylthio-2-oxobutanoate and 7,8 diaminononanoate. The latter compound is then dephosphorylated through a dethiobiotin synthetase resulting in a dethiobiotin. This compound interacts with a sulfurated[sulfur carrier), a hydrogen ion and a S-adenosylmethionine through a biotin synthase to produce Biotin and releasing l-methionine and a 5-deoxyadenosine. Biotin is then metabolized by a bifunctional protein resulting in pyrophosphate and Biotinyl-5-AMP which in turn reacts with the same protein (bifunctional protein birA resulting ina biotin caroxyl carrying protein.This product then enters the fatty acid biosynthesis. PW000762 ec00780 Metabolic Fatty acid biosynthesis The fatty acid biosynthesis starts from acetyl-CoA reacting either with a holo-[acp] through a 3-oxoacyl-[acp] synthase 3 resulting in an acetyl-[acp] or react with hydrogen carbonate through an ATP driven acetyl-CoA carboxylase resulting in a malonyl-CoA. Malonyl-CoA reacts with a holo-acp] through a malonyl-CoA-ACP transacylase resulting in a malonyl-[acp]. This compound can react with a KASI protein resulting in an acetyl-[acp]. A malonyl-[acp] can also react with an acetyl-[acp] through KASI and KASII or with acetyl-CoA through a beta-ketoacyl-ACP synthase to produce an acetoacetyl-[acp]. An acetoacetyl-[acp] is also known as a 3-oxoacyl-[acp]. A 3-oxoacyl-[acp] is reduced through a NDPH mediated 3-oxoacyl-[acp] reductase resulting in a (3R)-3-hydroxyacyl-[acp] (R3 hydroxydecanoyl-[acp]) which can either join the fatty acid metabolism, be dehydrated by an 3R-hydroxymyristoyl-[acp] dehydratase to produce a trans-2-enoyl-[acp] or be dehydrated by a hydroxydecanoyl-[acp] to produce a trans-delta2 decenoyl-[acp]. Trans-2-enoyl-[acp] is reduced by a NADH driven enoyl-[acp] reductase resulting in a 2,3,4-saturated fatty acyl-[acp]. This product then reacts with malonyl-[acp] through KASI and KASII resulting in a holo-acyl carrier protein and a 3- oxoacyl-[acp]. Trans-delta2 decenoyl-[acp] reacts with a 3-hydroxydecanoyl-[acp] dehydrase producing a cis-delta 3-decenoyl-ACP. This product then reacts with KASI to produce a 3-oxo-cis-delta5-dodecenoyl-[acp], which in turn is reduced by a NADPH driven 3-oxoacyl-[acp] resulting in a 3R-hydroxy cis delta5-dodecenoyl-acp. This product is dehydrated by a (3R)-hydroxymyristoyl-[acp] dehydratase resulting in a trans-delta 3- cis-delta 5-dodecenoyl-[acp] which in turn is reduced by a NADH driven enoyl-[acp] reductase resulting in a cis-delta5-dodecenoyl-acp which goes into fatty acid metabolism PW000900 ec00061 Metabolic Biosynthesis of unsaturated fatty acids ec01040 Metabolic pathways eco01100 Specdb::CMs 1085682 Specdb::NmrOneD 320531 Specdb::NmrOneD 320532 Specdb::NmrOneD 320533 Specdb::NmrOneD 320534 Specdb::NmrOneD 320535 Specdb::NmrOneD 320536 Specdb::NmrOneD 320537 Specdb::NmrOneD 320538 Specdb::NmrOneD 320539 Specdb::NmrOneD 320540 Specdb::NmrOneD 320541 Specdb::NmrOneD 320542 Specdb::NmrOneD 320543 Specdb::NmrOneD 320544 Specdb::NmrOneD 320545 Specdb::NmrOneD 320546 Specdb::NmrOneD 320547 Specdb::NmrOneD 320548 Specdb::NmrOneD 320549 Specdb::NmrOneD 320550 Specdb::MsMs 28130 Specdb::MsMs 28131 Specdb::MsMs 28132 Specdb::MsMs 34688 Specdb::MsMs 34689 Specdb::MsMs 34690 C00685 Acyl-[acyl-carrier protein] + Malonyl-[acyl-carrier protein] <> 3-Oxoacyl-[acyl-carrier protein] + Carbon dioxide + Acyl-carrier protein R02768 (3R)-3-Hydroxyacyl-[acyl-carrier protein] + NADP <> 3-Oxoacyl-[acyl-carrier protein] + NADPH + Hydrogen ion R02767