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Showing Compound 6-Hydroxyhexanoic acid (FDB029184)

Record Information
Version1.0
Creation date2011-09-21 01:51:23 UTC
Update date2015-07-21 06:59:39 UTC
Primary IDFDB029184
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6-Hydroxyhexanoic acid
Description6-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]
CAS Number1191-25-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5-CarboxypentanolChEBI
5-Hydroxypentanecarboxylic acidChEBI
6-Hydroxy caproic acidChEBI
6-Hydroxycaproic acidChEBI
6-HydroxyhexanoateChEBI
epsilon-Hydroxycaproic acidChEBI
epsilon-Hydroxyhexanoic acidChEBI
5-HydroxypentanecarboxylateGenerator
6-Hydroxy caproateGenerator
6-HydroxycaproateGenerator
epsilon-HydroxycaproateGenerator
epsilon-HydroxyhexanoateGenerator
6-Hydroxyhexanoic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility69.7 g/LALOGPS
logP0.29ALOGPS
logP0.37ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)4.71ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity33 m³·mol⁻¹ChemAxon
Polarizability14.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H12O3
IUPAC name6-hydroxyhexanoic acid
InChI IdentifierInChI=1S/C6H12O3/c7-5-3-1-2-4-6(8)9/h7H,1-5H2,(H,8,9)
InChI KeyIWHLYPDWHHPVAA-UHFFFAOYSA-N
Isomeric SMILESOCCCCCC(O)=O
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
Classification
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Straight chain fatty acid
  • Fatty acyl
  • Fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS6-Hydroxyhexanoic acid, non-derivatized, GC-MS Spectrumsplash10-0002-2910000000-e716906e6cfff1fe8280Spectrum
GC-MS6-Hydroxyhexanoic acid, non-derivatized, GC-MS Spectrumsplash10-000b-3900000000-40993af249322e692c7eSpectrum
GC-MS6-Hydroxyhexanoic acid, non-derivatized, GC-MS Spectrumsplash10-00ks-3900000000-2cef5bd8abc32978760eSpectrum
GC-MS6-Hydroxyhexanoic acid, non-derivatized, GC-MS Spectrumsplash10-0002-2910000000-e716906e6cfff1fe8280Spectrum
GC-MS6-Hydroxyhexanoic acid, non-derivatized, GC-MS Spectrumsplash10-000b-3900000000-40993af249322e692c7eSpectrum
GC-MS6-Hydroxyhexanoic acid, non-derivatized, GC-MS Spectrumsplash10-00ks-3900000000-2cef5bd8abc32978760eSpectrum
Predicted GC-MS6-Hydroxyhexanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-af2963e26a3090eb411aSpectrum
Predicted GC-MS6-Hydroxyhexanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9820000000-7e00127952e941ecee9bSpectrum
Predicted GC-MS6-Hydroxyhexanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Hydroxyhexanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a8088eacd86801cbaf622017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-5b779c4e5332478575cc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-76288a084d6a02586a2c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-3aa48f729f122be4de712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a1c68e5bb179dbd48ebd2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3900000000-6553d45b878b4896fa252017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9500000000-0fb0bf97042c7f9c82232017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-1a0fadab662757b403582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-7a599e4f4b0881d45d772017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01qi-4900000000-17b9ffeba434e24b5d112017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-ccbbb53893a6b3b0547a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9300000000-092fbfae7070731d2c482021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-9000000000-790bd1a70820471cbd762021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-02783816d58a8896d3bd2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-7900000000-63281c7d32db52f006392021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-9600000000-c5cbc9ed64f6700fd30d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-d991bce438e188e89b422021-09-24View Spectrum
NMRNot Available
ChemSpider ID13835
ChEMBL IDCHEMBL2006530
KEGG Compound IDC06103
Pubchem Compound ID14490
Pubchem Substance IDNot Available
ChEBI ID32383
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12843
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Alcohol dehydrogenase [NADP(+)]AKR1A1P14550
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference