2.0 2015-06-08 15:40:34 -0600 2015-08-05 16:22:05 -0600 ECMDB23875 M2MDB005550 (3R)-3-Hydroxyacyl-[acyl-carrier protein] An acyl-[acyl-carrier protein] where the acyl group is substituted at the pro-3R position by a hydroxy group 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone 3,7-Di-O-methylquercetin 3,7-O-Dimethylquercetin 5,3',4'-Trihydroxy-3,7-dimethoxyflavone C17H14O7 330.2889 330.073952802 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one DTHF COC1=CC2=C(C(O)=C1)C(=O)C(OC)=C(O2)C1=CC(O)=C(O)C=C1 InChI=1S/C17H14O7/c1-22-9-6-12(20)14-13(7-9)24-16(17(23-2)15(14)21)8-3-4-10(18)11(19)5-8/h3-7,18-20H,1-2H3 LUJAXSNNYBCFEE-UHFFFAOYSA-N logp 3.00 ALOGPS logs -3.72 ALOGPS solubility 6.33e-02 g/l ALOGPS logp 2.42 ChemAxon pka_strongest_acidic 8.14 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one ChemAxon average_mass 330.2889 ChemAxon mono_mass 330.073952802 ChemAxon smiles COC1=CC2=C(C(O)=C1)C(=O)C(OC)=C(O2)C1=CC(O)=C(O)C=C1 ChemAxon formula C17H14O7 ChemAxon inchi InChI=1S/C17H14O7/c1-22-9-6-12(20)14-13(7-9)24-16(17(23-2)15(14)21)8-3-4-10(18)11(19)5-8/h3-7,18-20H,1-2H3 ChemAxon inchikey LUJAXSNNYBCFEE-UHFFFAOYSA-N ChemAxon polar_surface_area 105.45 ChemAxon refractivity 86.1 ChemAxon polarizability 32.5 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge 0 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 22892 Specdb::CMs 41233 Specdb::CMs 133355 Specdb::CMs 141089 Specdb::MsMs 24575 Specdb::MsMs 24576 Specdb::MsMs 24577 Specdb::MsMs 31133 Specdb::MsMs 31134 Specdb::MsMs 31135 Specdb::MsMs 374117 Specdb::MsMs 374118 Specdb::MsMs 2822561 Specdb::MsMs 2822562 Specdb::MsMs 2822563 Specdb::MsMs 2860018 Specdb::MsMs 2860019 Specdb::MsMs 2860020 C01271 (3R)-3-Hydroxyacyl-[acyl-carrier protein] <> trans-2,3-Dehydroacyl-[acyl-carrier protein] + Water R10208 (3R)-3-Hydroxyacyl-[acyl-carrier protein] + NADP <> 3-Oxoacyl-[acyl-carrier protein] + NADPH + Hydrogen ion R02767