1.0 2011-09-21 01:51:23 UTC 2015-07-21 06:59:39 UTC FDB029184 6-Hydroxyhexanoic acid 6-Hydroxyhexanoate was identified as the immediate product of hexanoate w-hydroxylation by whole cells and was further oxidized into adipic acid and an unexpected metabolite identified as 2-tetrahydrofuranacetic acid. This same metabolite, together with adipic acid, was also detected when similarly induced cells were incubated with hexanoate or 1,6-hexanediol, but not with 6-oxohexanoate (adipic semialdehyde).Cells grown on hexanoate and incubated with 6-hydroxyhexanoate were also found to accumulate 2-tetrahydrofuranacetic acid, which was not further degraded. Utilization of 6-hydroxyhexanoate for growth was restricted to those organisms also able to utilize adipate. Similar observations were made with 1,6-hexanediol serving as the carbon source and cells obtained from one organism,Pseudomonas aeruginosa PAO, grown either on 1,6-hexanediol or 6-hydroxyhexanoate,were found to be well induced for both 6-oxohexanoate and adipate oxidation. The results indicate that 6-hydroxyhexanoate and 1,6-hexanediol are susceptible to both 1B- and w-oxidative attack; however, the former pathway appears to be of no physiological significance since it generates 2-tetrahydrofuranacetic acid as a nonmetabolizable intermediate, making w-oxidation via adipate the exclusive pathway for degradation. [HMDB] 5-Carboxypentanol 5-Hydroxypentanecarboxylate 5-Hydroxypentanecarboxylic acid 6-Hydroxy caproate 6-Hydroxy caproic acid 6-Hydroxycaproate 6-Hydroxycaproic acid 6-Hydroxyhexanoate 6-Hydroxyhexanoic acid epsilon-Hydroxycaproate epsilon-Hydroxycaproic acid epsilon-Hydroxyhexanoate epsilon-Hydroxyhexanoic acid C6H12O3 132.1577 132.07864425 6-hydroxyhexanoic acid 6-hydroxyhexanoic acid 1191-25-9 OCCCCCC(O)=O InChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9) IWHLYPDWHHPVAA-UHFFFAOYSA-N belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Medium-chain hydroxy acids and derivatives Organic compounds Organic acids and derivatives Hydroxy acids and derivatives Medium-chain hydroxy acids and derivatives Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Monocarboxylic acids and derivatives Organic oxides Primary alcohols Straight chain fatty acids Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Straight chain fatty acid 6-hydroxy monocarboxylic acid Hydroxy fatty acids Hydroxy fatty acids medium-chain fatty acid omega-hydroxy fatty acid straight-chain fatty acid Solid logp 0.29 ALOGPS logs -0.28 ALOGPS solubility 6.97e+01 g/l ALOGPS logp 0.37 ChemAxon pka_strongest_acidic 4.71 ChemAxon pka_strongest_basic -2 ChemAxon iupac 6-hydroxyhexanoic acid ChemAxon average_mass 132.1577 ChemAxon mono_mass 132.07864425 ChemAxon smiles OCCCCCC(O)=O ChemAxon formula C6H12O3 ChemAxon inchi InChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9) ChemAxon inchikey IWHLYPDWHHPVAA-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 33 ChemAxon polarizability 14.24 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 2794 Specdb::MsIr 2795 Specdb::MsIr 2796 Specdb::CMs 22019 Specdb::CMs 32223 Specdb::CMs 32224 Specdb::CMs 32225 Specdb::CMs 40001 Specdb::CMs 100022 Specdb::CMs 100023 Specdb::CMs 100024 Specdb::CMs 136193 Specdb::CMs 143927 Specdb::MsMs 314884 Specdb::MsMs 314885 Specdb::MsMs 314886 Specdb::MsMs 360724 Specdb::MsMs 360725 Specdb::MsMs 360726 Specdb::MsMs 437870 Specdb::MsMs 437871 Specdb::MsMs 437872 Specdb::MsMs 437873 Specdb::MsMs 437874 Specdb::MsMs 2766026 Specdb::MsMs 2766027 Specdb::MsMs 2766028 Specdb::MsMs 2943259 Specdb::MsMs 2943260 Specdb::MsMs 2943261 Specdb::NmrOneD 151850 Specdb::NmrOneD 151851 Specdb::NmrOneD 151852 Specdb::NmrOneD 151853 Specdb::NmrOneD 151854 Specdb::NmrOneD 151855 Specdb::NmrOneD 151856 Specdb::NmrOneD 151857 Specdb::NmrOneD 151858 Specdb::NmrOneD 151859 Specdb::NmrOneD 151860 Specdb::NmrOneD 151861 Specdb::NmrOneD 151862 Specdb::NmrOneD 151863 Specdb::NmrOneD 151864 Specdb::NmrOneD 151865 Specdb::NmrOneD 151866 Specdb::NmrOneD 151867 Specdb::NmrOneD 151868 Specdb::NmrOneD 151869 HMDB12843 32383 Alcohol dehydrogenase [NADP(+)] P14550 AKR1A1