Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-16 17:53:52 UTC
Update Date2023-02-21 17:30:24 UTC
HMDB IDHMDB0061681
Secondary Accession Numbers
  • HMDB61681
Metabolite Identification
Common Name6-(2-Hydroxyethoxy)-6-oxohexanoic acid
Description6-(2-Hydroxyethoxy)-6-oxohexanoic acid, also known as (2-hydroxyethyl) hydrogen adipate or adipinic acid ethylene glycol monoester, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 6-(2-Hydroxyethoxy)-6-oxohexanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1677000624
Synonyms
ValueSource
(2-Hydroxyethyl) hydrogen adipateChEBI
Adipinic acid ethylene glycol monoesterChEBI
(2-Hydroxyethyl) hydrogen adipic acidGenerator
Adipinate ethylene glycol monoesterGenerator
6-(2-Hydroxyethoxy)-6-oxohexanoateGenerator
Chemical FormulaC8H14O5
Average Molecular Weight190.1938
Monoisotopic Molecular Weight190.084123558
IUPAC Name6-(2-hydroxyethoxy)-6-oxohexanoic acid
Traditional Name6-(2-hydroxyethoxy)-6-oxohexanoic acid
CAS Registry NumberNot Available
SMILES
OCCOC(=O)CCCCC(O)=O
InChI Identifier
InChI=1S/C8H14O5/c9-5-6-13-8(12)4-2-1-3-7(10)11/h9H,1-6H2,(H,10,11)
InChI KeyYXCHMHANQUUDOV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.9 g/LALOGPS
logP-0.15ALOGPS
logP-0.054ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity43.8 m³·mol⁻¹ChemAxon
Polarizability19.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.85131661259
DarkChem[M-H]-141.36631661259
DeepCCS[M+H]+137.28930932474
DeepCCS[M-H]-133.45630932474
DeepCCS[M-2H]-170.29330932474
DeepCCS[M+Na]+146.03230932474
AllCCS[M+H]+141.732859911
AllCCS[M+H-H2O]+138.032859911
AllCCS[M+NH4]+145.032859911
AllCCS[M+Na]+146.032859911
AllCCS[M-H]-142.732859911
AllCCS[M+Na-2H]-144.032859911
AllCCS[M+HCOO]-145.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-(2-Hydroxyethoxy)-6-oxohexanoic acidOCCOC(=O)CCCCC(O)=O2769.5Standard polar33892256
6-(2-Hydroxyethoxy)-6-oxohexanoic acidOCCOC(=O)CCCCC(O)=O1477.4Standard non polar33892256
6-(2-Hydroxyethoxy)-6-oxohexanoic acidOCCOC(=O)CCCCC(O)=O1637.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-(2-Hydroxyethoxy)-6-oxohexanoic acid,1TMS,isomer #1C[Si](C)(C)OCCOC(=O)CCCCC(=O)O1736.9Semi standard non polar33892256
6-(2-Hydroxyethoxy)-6-oxohexanoic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CCCCC(=O)OCCO1655.0Semi standard non polar33892256
6-(2-Hydroxyethoxy)-6-oxohexanoic acid,2TMS,isomer #1C[Si](C)(C)OCCOC(=O)CCCCC(=O)O[Si](C)(C)C1773.6Semi standard non polar33892256
6-(2-Hydroxyethoxy)-6-oxohexanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCOC(=O)CCCCC(=O)O1990.4Semi standard non polar33892256
6-(2-Hydroxyethoxy)-6-oxohexanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCC(=O)OCCO1897.4Semi standard non polar33892256
6-(2-Hydroxyethoxy)-6-oxohexanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCOC(=O)CCCCC(=O)O[Si](C)(C)C(C)(C)C2224.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fic-9500000000-0e222c56ae25cf9f5a312017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0fk9-8960000000-f5ae7ec4ed8d73165d722017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 10V, Positive-QTOFsplash10-00dj-1900000000-1b68d3a4203c2d2b89462017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 20V, Positive-QTOFsplash10-0002-9700000000-74ee46188fad58a5dbd52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 40V, Positive-QTOFsplash10-054w-9100000000-8224f475309332a306f82017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 10V, Negative-QTOFsplash10-002k-1900000000-862b9632afa76aa395182017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 20V, Negative-QTOFsplash10-004m-5900000000-656ca77940e5cb87bc2b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 40V, Negative-QTOFsplash10-052f-9300000000-0ce808b8b3fda65ffd312017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 10V, Negative-QTOFsplash10-004r-2900000000-756bea861eac3d4fd6252021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 20V, Negative-QTOFsplash10-0kdi-3900000000-119b12f383058dddf1fb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 40V, Negative-QTOFsplash10-052f-9100000000-d73bc4edc984badc8eaf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 10V, Positive-QTOFsplash10-0f92-7900000000-ae0975d3d73f3e7bd2cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 20V, Positive-QTOFsplash10-0571-9300000000-205e81f900e4dda0abb82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-(2-Hydroxyethoxy)-6-oxohexanoic acid 40V, Positive-QTOFsplash10-0a4j-9000000000-a814d4787c2e88ff1a242021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4066086
PDB IDNot Available
ChEBI ID84086
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.