You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 14:17:32 UTC
Update Date2014-06-13 20:28:11 UTC
HMDB IDHMDB02030
Secondary Accession NumbersNone
Metabolite Identification
Common NameFructosamine
DescriptionFructosamine 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 ).
Structure
Thumb
Synonyms
  1. 1-Amino-1-deoxy-D-fructose
  2. D-Isoglucosamine
Chemical FormulaC6H13NO5
Average Molecular Weight179.1711
Monoisotopic Molecular Weight179.079372531
IUPAC Name(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol
Traditional Name(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol
CAS Registry Number4429-04-3
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 KeyIXZISFNWUWKBOM-ARQDHWQXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxane
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility990.0ALOGPS
logP-2.7ALOGPS
logP-2.9ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)10.71ChemAxon
pKa (Strongest Basic)8.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area116.17 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.02 m3·mol-1ChemAxon
Polarizability16.43 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1980 +/- 320 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified2300 (1850 - 2850) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified192 (149–242) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4750.0 +/- 2950.0 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified<1.00 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2220 +/- 250 uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified338.7 +/- 77.4 uMAdult (>18 years old)Both
Diabetes
details
BloodDetected and Quantified228 (180–255) uMAdult (>18 years old)BothCirrhosis details
BloodDetected and Quantified315 (260–430) uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified254 (193–315) uMAdult (>18 years old)Both
Diabetes mellitus type 2
details
BloodDetected and Quantified408 (346–653) uMAdult (>18 years old)Both
Diabetes mellitus type 2
details
Associated Disorders and Diseases
Disease References
11-beta-hydroxylase deficiency
  1. 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
Pregnancy
  1. 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
Diabetes mellitus type 2
  1. 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
Associated OMIM IDs
  • 125853 (Diabetes mellitus type 2)
  • 202010 (11-beta-hydroxylase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022807
KNApSAcK IDNot Available
Chemspider ID19291
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFructosamine
NuGOwiki LinkHMDB02030
Metagene LinkHMDB02030
METLIN IDNot Available
PubChem Compound20484
PDB IDNot Available
ChEBI ID24103
References
Synthesis ReferenceLiu, 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
  2. Armbruster DA: Fructosamine: structure, analysis, and clinical usefulness. Clin Chem. 1987 Dec;33(12):2153-63. Pubmed: 3319287

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
May initiate a process leading to the deglycation of fructoselysine and of glycated proteins. May play a role in the phosphorylation of 1-deoxy-1-morpholinofructose (DMF), fructoselysine, fructoseglycine, fructose and glycated lysozyme
Gene Name:
FN3K
Uniprot ID:
Q9H479
Molecular weight:
35170.9
General function:
Carbohydrate transport and metabolism
Specific function:
Phosphorylates psicosamines and ribulosamines, but not fructosamines, on the third carbon of the sugar moiety. Protein- bound psicosamine 3-phosphates and ribulosamine 3-phosphates are unstable and decompose under physiological conditions. Thus phosphorylation leads to deglycation
Gene Name:
FN3KRP
Uniprot ID:
Q9HA64
Molecular weight:
34412.0
General function:
Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
Specific function:
In the DNA of higher eukaryotes, hydrolytic deamination of 5-methylcytosine to thymine leads to the formation of G/T mismatches. This enzyme corrects G/T mispairs to G/C pairs. It is capable of hydrolyzing the carbon-nitrogen bond between the sugar- phosphate backbone of the DNA and a mispaired thymine. In addition to the G/T, it can remove thymine also from C/T and T/T mispairs in the order G/T >> C/T > T/T. It has no detectable activity on apyrimidinic sites and does not catalyze the removal of thymine from A/T pairs or from single-stranded DNA. It can also remove uracil and 5-bromouracil from mispairs with guanine
Gene Name:
TDG
Uniprot ID:
Q13569
Molecular weight:
46053.0