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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 16:31:23 UTC
Update Date2023-05-30 20:56:02 UTC
HMDB IDHMDB0005876
Secondary Accession Numbers
  • HMDB05876
Metabolite Identification
Common Name3-Deoxyfructose
Description3-Deoxyglucosone (3DG) is a dicarbonyl sugar used as a marker of hyperglycemia in diabetic patients (PMID: 10491986 ). 3DG is naturally synthesized from the Maillard reaction. It forms after glucose reacts with primary amino groups of lysine and arginine, found in proteins. 3DG also arises via the degradation of fructose 3-phsophate (PMID: 2300805 ). 3DG is highly reactive toward amine groups. It reacts with amino groups of proteins and forms advanced glycation end-products (AGEs). 3DG as well as AGEs play a role in the modification and cross-linking of long-lived proteins such as crystallin and collagen, contributing to diseases such as the vascular complications of diabetes, atherosclerosis, hypertension, Alzheimer's disease, inflammation, and aging (PMID: 27164965 , 10491986 , 9836531 , 9430981 ). 3DG inactivates aldehyde reductase (PMID: 7827091 ). Aldehyde reductase is the cellular enzyme that protects the body from 3DG. Detoxification of 3DG to 3-deoxyfructose (3DF) is impaired in diabetics. Aminoguanidine (AG) is an investigational drug used to deactivate 3-DG (PMID: 8194672 ).
Structure
Thumb
Synonyms
ValueSource
(4S,5R)-1,4,5,6-Tetrahydroxyhexan-2-oneChEBI
3-Deoxy-D-erythro-2-hexuloseChEBI
3-Deoxy-D-erythro-hexuloseChEBI
3-DeoxyhexuloseChEBI
3-DeoxyfructoseMeSH, ChEBI
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(4S,5R)-1,4,5,6-tetrahydroxyhexan-2-one
Traditional Name(4S,5R)-1,4,5,6-tetrahydroxyhexan-2-one
CAS Registry Number6196-57-2
SMILES
[H]OC([H])([H])C(=O)C([H])([H])[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])O[H]
InChI Identifier
InChI=1S/C6H12O5/c7-2-4(9)1-5(10)6(11)3-8/h5-8,10-11H,1-3H2/t5-,6+/m0/s1
InChI KeyOXFWZSUJNURRMW-NTSWFWBYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Beta-hydroxy ketone
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified7.12 (5.01-8.52) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
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 ID2338378
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3080627
PDB IDNot Available
ChEBI ID142685
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