Record Information
Version1.0
Creation date2011-09-21 00:23:50 UTC
Update date2015-10-09 22:32:29 UTC
Primary IDFDB023050
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,5-Anhydrosorbitol
Description1,5-Anhydrosorbitol or 1,5-anhydroglucitol (1,5-AG) is a validated marker of short-term glycemic control. This substance is derived mainly from food, is well absorbed in the intestine, and is distributed to all organs and tissues. It is metabolically stable, being excreted in the urine when its level exceeds the renal threshold. It is reabsorbed in the renal tubules, and is competitively inhibited by glucosuria, which leads to a reduction in its level in serum. The correlation between this reduction and the amount of glucose present in urine is so close that 1,5 AG can be used as a sensitive, day-to-day, real-time marker of glycemic control. It provides useful information on current glycemic control and is superior to both hemoglobin A1C and fructosamine in detecting near-normoglycemia. 1,5-AG in human plasma has been proposed for several years as a short-term, retrospective marker of glycaemic control and seems to be the most suitable parameter for monitoring glucose excursions. The decrease in serum 1,5-AG is very sensitive to urinary glucose excretion. It is a metabolically inert polyol that competes with glucose for reabsorption in the kidneys. Otherwise stable levels of 1,5-AG are rapidly depleted as blood glucose levels exceed the renal threshold for glucosuria. 1,5-AG is also more tightly associated with glucose fluctuations and postprandial glucose. (PMID: 18088226, 12166605, 7783360, 8940824) [HMDB]
CAS Number154-58-5
Structure
Thumb
Synonyms
SynonymSource
1,5-Anhydro-D-sorbitolChEBI
1,5-AnhydroglucitolChEBI
1,5-AGHMDB
1,5-Anhydro-D-glucitolHMDB
1-DeoxyglucoseHMDB
AceritolHMDB
PolygalitolHMDB
1-Deoxy-D-glucoseHMDB
1,5-SorbitanHMDB
1-Deoxy-D-glucopyranoseHMDB
1,5-ANHYDROSORBITOLChEBI
1,5-anhydro-D-glucitolhmdb
Predicted Properties
PropertyValueSource
Water Solubility1040 g/LALOGPS
logP-2.6ALOGPS
logP-2.6ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)12.66ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.89 m³·mol⁻¹ChemAxon
Polarizability15.19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H12O5
IUPAC name(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3-,4+,5+,6+/m0/s1
InChI KeyMPCAJMNYNOGXPB-SLPGGIOYSA-N
Isomeric SMILESOC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrumsplash10-00kb-0930000000-3e9a279cc11867623df9Spectrum
GC-MS1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrumsplash10-00kb-0930000000-3e9a279cc11867623df9Spectrum
GC-MS1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrumsplash10-0gb9-0900000000-3b72b858c9bcc30c45b1Spectrum
GC-MS1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrumsplash10-0fr2-0920000000-5ad690bbbd7fce791cceSpectrum
Predicted GC-MS1,5-Anhydrosorbitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9600000000-614246ddd5b68d2ed62dSpectrum
Predicted GC-MS1,5-Anhydrosorbitol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01di-4169300000-4fef5d885796ecad0f89Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-6900000000-9a919af22cbe7d86b80dSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9100000000-f5cab1c2b02d65ad346aSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-ced7163dcc8f3ebdbbceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0w30-0900000000-7cd7be2b3ef8c9d328e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-c8a9b1625a999852f120Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1900000000-60691e9a1518b8f9eacdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bi-9200000000-e9e5be081f31a0ee52fdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-c6502965757c84521bf7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1900000000-944d7cc4495151774511Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9100000000-eea65e515404cb15787aSpectrum
NMRNot Available
ChemSpider ID58485
ChEMBL IDCHEMBL344637
KEGG Compound IDC07326
Pubchem Compound ID64960
Pubchem Substance IDNot Available
ChEBI ID16070
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02712
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDASO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference