Human Metabolome Database Version 3.5

Showing metabocard for Fructosamine (HMDB02030)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:32 -0600
Update Date 2013-05-29 13:33:29 -0600
HMDB ID HMDB02030
Secondary Accession Numbers None
Metabolite Identification
Common Name Fructosamine
Description Fructosamine is a compound which can be considered as the result of a reaction between fructose and ammonia or an amine (with a molecule of water being released). A fructosamine is also formed when carbonyl group of glucose reacts with an amino group of a protein, as the double bond to oxygen moves from the end carbon atom to the next carbon atom and water is released. Fructosamines formed from blood proteins such as serum albumin are known as Glycated Serum Protein (GSP) or Glycated Albumin, and are used to identify the plasma glucose concentration over time and so assess diabetic control. (wikipedia). Glucose molecules are joined to protein molecules to form stable ketoamines, or fructosamines, through glycation, a nonenzymatic mechanism involving a labile Schiff base intermediate and the Amadori rearrangement. The amount of fructosamine in serum is increased in diabetes mellitus owing to the abnormally high concentration of sugar in blood. The concentration of fructosamine in serum thus reflects the degree of glycemic control attained by the diabetic patient and is useful in monitoring the effectiveness of therapy in diabetes over a period of several weeks, in a manner analogous to the determination of glycated hemoglobin. Of the analytical approaches used to measure fructosamine, affinity chromatography with m-aminophenylboronic acid and the nitroblue tetrazolium reduction method appear to be the most practical means for clinical chemists to assay fructosamine quickly, economically, and accurately. Fructosamine values can readily distinguish normal individuals and diabetic patients in good glycemic control from diabetics in poor control. Unlike glycated hemoglobin, which reflects the average blood sugar concentration over the past six to eight weeks, fructosamine reflects the average blood sugar concentration over the past two to three weeks. Thus a clinical advantage is that fructosamine responds more quickly to changes in therapy, thereby allowing for improved glycemic control. Fructosamine is used in conjunction with determinations of blood sugar and (or) of glycated hemoglobin, or by itself, the fructosamine assay can provide clinically useful information for the detection and control of diabetes. (PMID: 3319287 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Amino-1-deoxy-D-fructose
  2. D-Isoglucosamine
Chemical Formula C6H13NO5
Average Molecular Weight 179.1711
Monoisotopic Molecular Weight 179.079372531
IUPAC Name (2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name (2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol
CAS Registry Number 4429-04-3
SMILES NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier InChI=1S/C6H13NO5/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,8-11H,1-2,7H2/t3-,4-,5+,6-/m1/s1
InChI Key IXZISFNWUWKBOM-ARQDHWQXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxane
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct Parent Hexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 990 g/L ALOGPS
LogP -2.71 ALOGPS
LogP -2.9 ChemAxon
LogS 0.74 ALOGPS
pKa (strongest acidic) 10.71 ChemAxon
pKa (strongest basic) 8.17 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 116.17 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 38.02 ChemAxon
Polarizability 16.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Saliva
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1980 +/- 320 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
2300 (1850 - 2850) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
192 (149–242) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
4750.0 +/- 2950.0 uM Adult (>18 years old) Female Normal
Saliva Detected and Quantified
<1.00 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 2220 +/- 250 uM Adult (>18 years old) Female Pregnancy
Blood Detected and Quantified 338.7 +/- 77.4 uM Adult (>18 years old) Both Comment Diabetes
Blood Detected and Quantified 228 (180–255) uM Adult (>18 years old) Both Cirrhosis
Blood Detected and Quantified 315 (260–430) uM Adult (>18 years old) Both Renal disease
Blood Detected and Quantified 254 (193–315) uM Adult (>18 years old) Both Type 2 diabetes (Good control)
Blood Detected and Quantified 408 (346–653) uM Adult (>18 years old) Both Type 2 diabetes (Poor control)
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  • Guevara-Aguirre J, Guevara-Aguirre M, Saavedra J, Bernstein G, Rosenbloom AL: Comparison of oral insulin spray and subcutaneous regular insulin at mealtime in type 1 diabetes. Diabetes Technol Ther. 2007 Aug;9(4):372-6. Pubmed: 17705693 Link_out
      Pregnancy
      • Khan HA, Sobki SH, Alhomida AS: Fluctuations in fasting blood glucose and serum fructosamine in pregnant women monitored on successive antenatal visits. Clin Exp Med. 2006 Oct;6(3):134-7. Pubmed: 17061063 Link_out
          11-beta-hydroxylase deficiency
          • Paroni R, Ceriotti F, Galanello R, Battista Leoni G, Panico A, Scurati E, Paleari R, Chemello L, Quaino V, Scaldaferri L, Lapolla A, Mosca A: Performance characteristics and clinical utility of an enzymatic method for the measurement of glycated albumin in plasma. Clin Biochem. 2007 Dec;40(18):1398-405. Epub 2007 Aug 10. Pubmed: 17919531 Link_out
              Associated OMIM IDs
              • 125853 Link_out (Diabetes mellitus type 2)
              • 202010 Link_out (11-beta-hydroxylase deficiency)
              DrugBank ID Not Available
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB022807
              KNApSAcK ID Not Available
              Chemspider ID 19291 Link_out
              KEGG Compound ID Not Available
              BioCyc ID Not Available
              BiGG ID Not Available
              Wikipedia Link Fructosamine Link_out
              NuGOwiki Link HMDB02030 Link_out
              Metagene Link HMDB02030 Link_out
              METLIN ID Not Available
              PubChem Compound 20484 Link_out
              PDB ID Not Available
              ChEBI ID 24103 Link_out
              References
              Synthesis Reference Liu, Gui-Rong; Qiu, Ye; Yang, Qun-Shui. Synthesis of fructosamine and its application in cigarettes. Yancao Keji (2006), (8), 33-34, 37.
              Material Safety Data Sheet (MSDS) Download (PDF)
              General References
              1. Morenkova SA: [Comparative analysis of dependence of saliva sorbitol and fructosamine levels on blood glucose level in patients with diabetes] Biomed Khim. 2004;50(6):612-4. Pubmed: 15707277 Link_out
              2. Armbruster DA: Fructosamine: structure, analysis, and clinical usefulness. Clin Chem. 1987 Dec;33(12):2153-63. Pubmed: 3319287 Link_out

              Enzymes
              Name: Fructosamine-3-kinase
              Reactions: Not Available
              Gene Name: FN3K
              Uniprot ID: Q9H479 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Ketosamine-3-kinase
              Reactions: Not Available
              Gene Name: FN3KRP
              Uniprot ID: Q9HA64 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: G/T mismatch-specific thymine DNA glycosylase
              Reactions: Not Available
              Gene Name: TDG
              Uniprot ID: Q13569 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA