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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:05 UTC
HMDB IDHMDB0000346
Secondary Accession Numbers
  • HMDB00346
Metabolite Identification
Common Name3-Deoxyarabinohexonic acid
Description3-Deoxyarabinohexonic acid, also known as arabino-3-deoxyhexonate or D-2-keto-3-deoxygluconate, 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. 3-Deoxyarabinohexonic acid is a drug. 3-Deoxyarabinohexonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752125
Synonyms
ValueSource
3-DeoxyarabinohexonateGenerator
(2S,4S,5R)-2,4,5,6-TetrahydroxyhexanoateHMDB
(2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoic acidHMDB
3-Deoxy-arabino-hexonateHMDB
3-Deoxy-arabino-hexonic acidHMDB
3-Deoxy-D-arabino-hexonic acidHMDB
3-Deoxyarabino-hexonic acidHMDB
Arabino-3-deoxyhexonateHMDB
Arabino-3-deoxyhexonic acidHMDB
D-2-Keto-3-deoxygluconateHMDB
3-Deoxy-arabino-hexonic acid, monosodium salt, (D)-isomerHMDB
3-Deoxy-arabino-hexonic acid, (D)-isomerHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(2S,4S,5R)-2,4,5,6-tetrahydroxyhexanoic acid
Traditional Name3-deoxy-arabinohexonic acid
CAS Registry Number29625-79-4
SMILES
OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1
InChI KeyYGMNHEPVTNXLLS-VAYJURFESA-N
Chemical Taxonomy
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
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility255 g/LALOGPS
logP-2.5ALOGPS
logP-2.7ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.17 m³·mol⁻¹ChemAxon
Polarizability16.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xr-9300000000-2c51a274d3829236fb3dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004r-9011830000-6fd8133dd7e3fd46d86fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ea-2900000000-881714d3fd59cb3dce87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000m-9500000000-362f55e67fe8e5ad72afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009l-9100000000-63e26dab8c3fd216fccfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5900000000-1708165ec6bea9405ae6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9300000000-69eedad8f8133d91c93eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05g3-9200000000-0f8904ef71f095754d68Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDDB03303
Phenol Explorer Compound IDNot Available
FooDB IDFDB021969
KNApSAcK IDNot Available
Chemspider ID134838
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5335
PubChem Compound152990
PDB IDSSH
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceHanninen, Kari; Niemela, Klaus. Alkaline degradation of peat humic acids. Part II. Identification of hydrophilic products. Acta Chemica Scandinavica (1992), 46(5), 459-63.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Schoots AC, Mikkers FE, Cramers CA, Ringoir S: Profiling of uremic serum by high-resolution gas chromatography-electron-impact, chemical ionization mass spectrometry. J Chromatogr. 1979 Sep 11;164(1):1-8. [PubMed:541389 ]
  2. Schoots AC, Leclercq PA: Chemical ionization mass spectrometry of trimethylsilylated carbohydrates and organic acids retained in uremic serum. Biomed Mass Spectrom. 1979 Nov;6(11):502-7. [PubMed:534687 ]