1.02011-09-21 01:51:23 UTC2015-07-21 06:59:39 UTCFDB0291846-Hydroxyhexanoic acid6-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-Carboxypentanol5-Hydroxypentanecarboxylate5-Hydroxypentanecarboxylic acid6-Hydroxy caproate6-Hydroxy caproic acid6-Hydroxycaproate6-Hydroxycaproic acid6-Hydroxyhexanoate6-Hydroxyhexanoic acidepsilon-Hydroxycaproateepsilon-Hydroxycaproic acidepsilon-Hydroxyhexanoateepsilon-Hydroxyhexanoic acidC6H12O3132.1577132.078644256-hydroxyhexanoic acid6-hydroxyhexanoic acid1191-25-9OCCCCCC(O)=OInChI=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 derivativesOrganic compoundsOrganic acids and derivativesHydroxy acids and derivativesMedium-chain hydroxy acids and derivativesAliphatic acyclic compoundsCarbonyl compoundsCarboxylic acidsHydrocarbon derivativesHydroxy fatty acidsMedium-chain fatty acidsMonocarboxylic acids and derivativesOrganic oxidesPrimary alcoholsStraight chain fatty acidsAlcoholAliphatic acyclic compoundCarbonyl groupCarboxylic acidCarboxylic acid derivativeFatty acidFatty acylHydrocarbon derivativeHydroxy fatty acidMedium-chain fatty acidMedium-chain hydroxy acidMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundPrimary alcoholStraight chain fatty acid6-hydroxy monocarboxylic acidHydroxy fatty acidsHydroxy fatty acidsmedium-chain fatty acidomega-hydroxy fatty acidstraight-chain fatty acidSolidlogp0.29logs-0.28solubility6.97e+01 g/llogp0.37pka_strongest_acidic4.71pka_strongest_basic-2iupac6-hydroxyhexanoic acidaverage_mass132.1577mono_mass132.07864425smilesOCCCCCC(O)=OformulaC6H12O3inchiInChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9)inchikeyIWHLYPDWHHPVAA-UHFFFAOYSA-Npolar_surface_area57.53refractivity33polarizability14.24rotatable_bond_count5acceptor_count3donor_count2physiological_charge-1formal_charge0Specdb::MsIr2794Specdb::MsIr2795Specdb::MsIr2796Specdb::CMs22019Specdb::CMs32223Specdb::CMs32224Specdb::CMs32225Specdb::CMs40001Specdb::CMs100022Specdb::CMs100023Specdb::CMs100024Specdb::CMs136193Specdb::CMs143927Specdb::NmrOneD151850Specdb::NmrOneD151851Specdb::NmrOneD151852Specdb::NmrOneD151853Specdb::NmrOneD151854Specdb::NmrOneD151855Specdb::NmrOneD151856Specdb::NmrOneD151857Specdb::NmrOneD151858Specdb::NmrOneD151859Specdb::NmrOneD151860Specdb::NmrOneD151861Specdb::NmrOneD151862Specdb::NmrOneD151863Specdb::NmrOneD151864Specdb::NmrOneD151865Specdb::NmrOneD151866Specdb::NmrOneD151867Specdb::NmrOneD151868Specdb::NmrOneD151869Specdb::MsMs314884Specdb::MsMs314885Specdb::MsMs314886Specdb::MsMs360724Specdb::MsMs360725Specdb::MsMs360726Specdb::MsMs437870Specdb::MsMs437871Specdb::MsMs437872Specdb::MsMs437873Specdb::MsMs437874Specdb::MsMs2766026Specdb::MsMs2766027Specdb::MsMs2766028Specdb::MsMs2943259Specdb::MsMs2943260Specdb::MsMs2943261HMDB1284332383Alcohol dehydrogenase [NADP(+)]P14550AKR1A1