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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:05 UTC
Update Date2017-12-07 01:49:27 UTC
HMDB IDHMDB0002712
Secondary Accession Numbers
  • HMDB02712
  • HMDB11726
  • HMDB11736
Metabolite Identification
Common 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 ).
Structure
Thumb
Synonyms
ValueSource
1,5-anhydro-D-SorbitolChEBI
1,5-AnhydroglucitolChEBI
1,5-AGHMDB
1,5-anhydro-D-GlucitolHMDB
1-DeoxyglucoseMeSH
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name1,5-anhydroglucitol
CAS Registry Number154-58-5
SMILES
OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as monosaccharides. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 - 143 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0930000000-3e9a279cc11867623df9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0930000000-3e9a279cc11867623df9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-0900000000-3b72b858c9bcc30c45b1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0920000000-5ad690bbbd7fce791cceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9600000000-614246ddd5b68d2ed62dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-01di-4169300000-4fef5d885796ecad0f89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-6900000000-9a919af22cbe7d86b80dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9100000000-f5cab1c2b02d65ad346aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-ced7163dcc8f3ebdbbceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0w30-0900000000-7cd7be2b3ef8c9d328e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-c8a9b1625a999852f120View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1900000000-60691e9a1518b8f9eacdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bi-9200000000-e9e5be081f31a0ee52fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-c6502965757c84521bf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1900000000-944d7cc4495151774511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9100000000-eea65e515404cb15787aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Sweat
Tissue Location
  • Prostate
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified130.0 (95.0 - 178.0) uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified150.0 (140 - 171) uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified150.0 (73.0 - 243.0) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified53.0 (11.0-95.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified25.0 +/- 13.0 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified110.9 +/- 30.2 uMAdult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SweatDetected but not Quantified Adult BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30.0 (9.7 - 66.4) uMAdolescent (13-18 years old)Both
Diabetes
details
BloodDetected and Quantified62.0 +/- 38.0 uMAdult (>18 years old)Both
Diabetes
details
BloodDetected but not Quantified Adult (>18 years old)BothPancreatic Cancer details
BloodDetected and Quantified50.0 (18.5 - 95.0) uMAdult (>18 years old)Not Specified
Diabetes
details
Cerebrospinal Fluid (CSF)Detected and Quantified41.7 +/-13.7 uMAdult (>18 years old)BothAlzheimer's disease details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]
Diabetes mellitus type 2
  1. Dungan KM, Buse JB, Largay J, Kelly MM, Button EA, Kato S, Wittlin S: 1,5-anhydroglucitol and postprandial hyperglycemia as measured by continuous glucose monitoring system in moderately controlled patients with diabetes. Diabetes Care. 2006 Jun;29(6):1214-9. [PubMed:16731998 ]
  2. Stickle D, Turk J: A kinetic mass balance model for 1,5-anhydroglucitol: applications to monitoring of glycemic control. Am J Physiol. 1997 Oct;273(4 Pt 1):E821-30. [PubMed:9357814 ]
  3. Nguyen TM, Rodriguez LM, Mason KJ, Heptulla RA: Serum 1,5-anhydroglucitol (Glycomark) levels in children with and without type 1 diabetes mellitus. Pediatr Diabetes. 2007 Aug;8(4):214-9. [PubMed:17659063 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023050
KNApSAcK IDNot Available
Chemspider ID58485
KEGG Compound IDC07326
BioCyc ID15-ANHYDRO-D-GLUCITOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3775
PubChem Compound64960
PDB IDASO
ChEBI ID16070
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
  3. Servo C, Pitkanen E: Variation in polyol levels in cerebrospinal fluid and serum in diabetic patients. Diabetologia. 1975 Dec;11(6):575-80. [PubMed:1205026 ]
  4. Sode K, Sugiura H, Tsugawa W, Watazu Y, Hamafuji T: Enzyme electrochemical preparation of a 3-keto derivative of 1,5-anhydro-D-glucitol using glucose-3-dehydrogenase. Appl Biochem Biotechnol. 2000 Spring;84-86:947-54. [PubMed:10849848 ]
  5. Yoshioka S, Saitoh S, Fujisawa T, Fujimori A, Takatani O, Funabashi M: Identification and metabolic implication of 1-deoxyglucose (1,5-anhydroglucitol) in human plasma. Clin Chem. 1982 Jun;28(6):1283-6. [PubMed:7074934 ]
  6. Yamanouchi T, Minoda S, Ogata N, Tachibana Y, Sekino N, Miyashita H, Akaoka I: Prolonged hyperalimentation as a possible cause of renal tubular dysfunction: evaluation of 1,5-anhydro-D-glucitol resorption and N-acetylglucosaminidase excretion in humans. Clin Sci (Lond). 1995 Feb;88(2):203-10. [PubMed:7720346 ]
  7. Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]
  8. Dworacka M, Winiarska H, Szymanska M, Kuczynski S, Szczawinska K, Wierusz-Wysocka B: 1,5-anhydro-D-glucitol: a novel marker of glucose excursions. Int J Clin Pract Suppl. 2002 Jul;(129):40-4. [PubMed:12166605 ]
  9. Akanuma Y, Morita M, Fukuzawa N, Yamanouchi T, Akanuma H: Urinary excretion of 1,5-anhydro-D-glucitol accompanying glucose excretion in diabetic patients. Diabetologia. 1988 Nov;31(11):831-5. [PubMed:3234638 ]
  10. Dungan KM: 1,5-anhydroglucitol (GlycoMark) as a marker of short-term glycemic control and glycemic excursions. Expert Rev Mol Diagn. 2008 Jan;8(1):9-19. [PubMed:18088226 ]
  11. Matsuyama T, Katayama Y, Fujita S: [Recent progress in evaluation of glycemic control by glycated protein and 1,5-AG]. Rinsho Byori. 1995 May;43(5):445-8. [PubMed:7783360 ]
  12. Saito H, Ohtomo T, Inui K: Na(+)-dependent uptake of 1,5-anhydro-D-glucitol via the transport systems for D-glucose and D-mannose in the kidney epithelial cell line, LLC-PK1. Nihon Jinzo Gakkai Shi. 1996 Oct;38(10):435-40. [PubMed:8940824 ]

Enzymes

General function:
Not Available
Specific function:
Catalyzes the NADPH-dependent reduction of 1,5-anhydro-D-fructose (AF) to 1,5-anhydro-D-glucitol. Can also catalyze the reduction of various aldehydes and quinones (By similarity). Has low NADPH-dependent reductase activity towards 9,10-phenanthrenequinone (in vitro).
Gene Name:
AKR1E2
Uniprot ID:
Q96JD6
Molecular weight:
36588.935
Reactions
1,5-Anhydrosorbitol + NADP → D-1,5-Anhydrofructose + NADPHdetails