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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:01:31 UTC
Update Date2022-03-07 02:54:01 UTC
HMDB IDHMDB0034223
Secondary Accession Numbers
  • HMDB34223
Metabolite Identification
Common Name2,3,4,5,6-Penta-O-acetyl-D-glucose
Description2,3,4,5,6-Penta-O-acetyl-D-glucose, also known as glucose pentaacetate or penta-O-acetyl-alpha-D-glucopyranose, belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 2,3,4,5,6-Penta-O-acetyl-D-glucose is a bitter tasting compound. Based on a literature review very few articles have been published on 2,3,4,5,6-Penta-O-acetyl-D-glucose.
Structure
Data?1563862530
Synonyms
ValueSource
1,2,3,4,6-Penta-O-acetyl-alpha-D-glucopyranosideMeSH
Glucose pentaacetateMeSH
Glucose pentaacetate, (D)-isomerMeSH
Glucose pentaacetate, (alpha-D)-isomerMeSH
Glucose pentaacetate, (beta-(D))-isomerMeSH
Penta-O-acetyl-alpha-D-glucopyranoseMeSH
Penta-O-acetylglucopyranoseMeSH
Beta-D-Glucopyranose pentaacetateChEMBL, HMDB
b-D-Glucopyranose pentaacetateGenerator, HMDB
b-D-Glucopyranose pentaacetic acidGenerator, HMDB
beta-D-Glucopyranose pentaacetic acidGenerator, HMDB
β-D-glucopyranose pentaacetateGenerator, HMDB
β-D-glucopyranose pentaacetic acidGenerator, HMDB
D-Glucose pentaacetateHMDB
D-Glucose, 2,3,4,5,6-pentaacetateHMDB
FEMA 2524HMDB
Glucose 2,3,4,5,6-pentaacetateHMDB
[(2R,3R,4S,5R,6S)-3,4,5,6-Tetrakis(acetyloxy)oxan-2-yl]methyl acetic acidGenerator
beta-D-Glucose pentaacetateMeSH
Chemical FormulaC16H22O11
Average Molecular Weight390.3393
Monoisotopic Molecular Weight390.116211546
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number3891-59-6
SMILES
CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
InChI Identifier
InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16-/m1/s1
InChI KeyLPTITAGPBXDDGR-IBEHDNSVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassPentacarboxylic acids and derivatives
Direct ParentPentacarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pentacarboxylic acid or derivatives
  • Oxane
  • Monosaccharide
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling Point454.00 to 456.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.5 mg/mL at 18 °CNot Available
LogP0.63Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.62 g/LALOGPS
logP0.53ALOGPS
logS-1.8ALOGPS
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.83331661259
DarkChem[M-H]-183.0831661259
DeepCCS[M+H]+177.37430932474
DeepCCS[M-H]-174.97930932474
DeepCCS[M-2H]-207.87230932474
DeepCCS[M+Na]+183.28730932474
AllCCS[M+H]+187.132859911
AllCCS[M+H-H2O]+184.632859911
AllCCS[M+NH4]+189.332859911
AllCCS[M+Na]+190.032859911
AllCCS[M-H]-188.432859911
AllCCS[M+Na-2H]-188.932859911
AllCCS[M+HCOO]-189.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3,4,5,6-Penta-O-acetyl-D-glucoseCC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O3325.4Standard polar33892256
2,3,4,5,6-Penta-O-acetyl-D-glucoseCC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O1984.6Standard non polar33892256
2,3,4,5,6-Penta-O-acetyl-D-glucoseCC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O2092.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose EI-B (Non-derivatized)splash10-0k97-5930000000-e21c830a522243fe6a572017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose EI-B (Non-derivatized)splash10-0k97-5930000000-e21c830a522243fe6a572018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1139000000-3ad29b7ec1ee51f6cccc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 10V, Positive-QTOFsplash10-001s-1049000000-735fd11b19acc0cfec1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 20V, Positive-QTOFsplash10-053i-1169000000-9de811ff6439bdded06a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 40V, Positive-QTOFsplash10-01p9-5192000000-6ef079e665faaf42b9412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 10V, Negative-QTOFsplash10-052k-6019000000-421048e865237bb9f8532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 20V, Negative-QTOFsplash10-0a4r-9223000000-5f54ba2bb711fac1cedb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 40V, Negative-QTOFsplash10-0a4i-9120000000-78e14e14341a24df674f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 10V, Positive-QTOFsplash10-001i-0039000000-6727197cbcc39b91f8bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 20V, Positive-QTOFsplash10-007y-2159000000-2630e5cbf0e62b819ed02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 40V, Positive-QTOFsplash10-014j-5894000000-4df8062522da6a3562492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 10V, Negative-QTOFsplash10-000i-0059000000-8d110703cdba61c450a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 20V, Negative-QTOFsplash10-0a4i-9044000000-e7150f1faec6f8527f002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,4,5,6-Penta-O-acetyl-D-glucose 40V, Negative-QTOFsplash10-0a4j-9047000000-5bdf67e006b51e242b242021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012529
KNApSAcK IDNot Available
Chemspider ID2006823
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2724702
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1495171
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .