1,5-Anhydrosorbitol (CHEM035465)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:47:20 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035465
Identification
Common Name1,5-Anhydrosorbitol
ClassSmall Molecule
DescriptionAn anhydro sugar of D-glucitol.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,5-Anhydro-D-sorbitolChEBI
1,5-AnhydroglucitolChEBI
1,5-AGHMDB
1,5-anhydro-D-GlucitolHMDB
1-DeoxyglucoseMeSH, HMDB
1,5-ANHYDROSORBITOLChEBI
AceritolMeSH, HMDB
PolygalitolMeSH, HMDB
1-Deoxy-D-glucoseMeSH, HMDB
1,5-SorbitanMeSH, HMDB
1-Deoxy-D-glucopyranoseMeSH, HMDB
Chemical FormulaC6H12O5
Average Molecular Mass164.157 g/mol
Monoisotopic Mass164.068 g/mol
CAS Registry Number154-58-5
IUPAC Name(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name1,5-anhydroglucitol
SMILESOC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0930000000-3e9a279cc11867623df9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0930000000-3e9a279cc11867623df9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-0900000000-3b72b858c9bcc30c45b1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0920000000-5ad690bbbd7fce791cceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9600000000-614246ddd5b68d2ed62dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-01di-4169300000-4fef5d885796ecad0f89Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-6900000000-9a919af22cbe7d86b80dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9100000000-f5cab1c2b02d65ad346aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-ced7163dcc8f3ebdbbceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0w30-0900000000-7cd7be2b3ef8c9d328e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-c8a9b1625a999852f120Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1900000000-60691e9a1518b8f9eacdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00bi-9200000000-e9e5be081f31a0ee52fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-c6502965757c84521bf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1900000000-944d7cc4495151774511Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9100000000-eea65e515404cb15787aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016s-0900000000-11ed18d0db7491144ffdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-9700000000-5e4a2cbe1835cdf91d56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9000000000-b6c715de68810d7109e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-20c29efaf1999d1f7f7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btc-9300000000-d09212a569ed1403170eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3b59d6f226c5762f52c0Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002712
FooDB IDFDB023050
Phenol Explorer IDNot Available
KNApSAcK IDC00052531
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3775
PDB IDNot Available
Wikipedia Link1,5-Anhydroglucitol
Chemspider ID58485
ChEBI ID16070
PubChem Compound ID64960
Kegg Compound IDC07326
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15277408
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18492944
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19796288
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.
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.
6. Servo C, Pitkanen E: Variation in polyol levels in cerebrospinal fluid and serum in diabetic patients. Diabetologia. 1975 Dec;11(6):575-80.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.