Showing Compound Fructosamine (FDB022807)

Record Information

Version

1.0

Creation date

2011-09-21 00:19:54 UTC

Update date

2018-05-29 01:52:53 UTC

Primary ID

FDB022807

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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. It 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) [HMDB]

CAS Number

4429-04-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	990 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-2.9	ChemAxon
logS	0.74	ALOGPS
pKa (Strongest Acidic)	10.71	ChemAxon
pKa (Strongest Basic)	8.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	116.17 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.02 m³·mol⁻¹	ChemAxon
Polarizability	16.43 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H13NO5

IUPAC name

(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol

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

Isomeric SMILES

NC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

179.1711

Monoisotopic Molecular Weight

179.079372531

Classification

Description

Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Monosaccharide
Oxane
Hemiacetal
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Primary amine
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

11-beta-hydroxylase deficiency

Disposition

Biological location:

Biofluid and excreta:

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Fructosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9300000000-4706e786831a83f7fdae	Spectrum
Predicted GC-MS	Fructosamine, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-2920100000-72782c8bd8e44300b317	Spectrum
Predicted GC-MS	Fructosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-fa504cd79cbfd6e45f1f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-2900000000-5e5687353a546e6c16ef	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05ar-9200000000-4e65a2b6f1c459eb13c9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fu-9600000000-5119143995339c78ad83	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-9700000000-41083fc8476785e53998	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2584bd1445d20f6e5747	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-0900000000-4d89cae6c9a7e59fca4a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-7900000000-cf9880807567a3cb2752	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ox-9000000000-28e351a8717de586ec69	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-6900000000-ffe71ad3e65f7b31f76e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adi-9200000000-5096012007a6fe6dd9f7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9000000000-39cc27e8040279e219a0	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

19291

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

20484

Pubchem Substance ID

Not Available

ChEBI ID

24103

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02030

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Fructosamine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB