Record Information
Version1.0
Creation date2011-09-21 00:15:44 UTC
Update date2020-09-17 15:38:54 UTC
Primary IDFDB022550
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6-Phosphogluconic acid
Description6-Phosphogluconic acid, also known as 6-phospho-D-gluconate or gluconate 6-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. A gluconic acid phosphate having the phosphate group at the 6-position. 6-Phosphogluconic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphogluconic acid exists in all living species, ranging from bacteria to humans. Within humans, 6-phosphogluconic acid participates in a number of enzymatic reactions. In particular, 6-phosphogluconic acid can be biosynthesized from gluconolactone through its interaction with the enzyme 6-phosphogluconolactonase. In addition, 6-phosphogluconic acid can be converted into D-ribulose 5-phosphate through the action of the enzyme 6-phosphogluconate dehydrogenase, decarboxylating. In humans, 6-phosphogluconic acid is involved in the metabolic disorder called the glucose-6-phosphate dehydrogenase deficiency pathway. Outside of the human body, 6-Phosphogluconic acid has been detected, but not quantified in, several different foods, such as teffs, chinese chestnuts, cottonseeds, irish moss, and red beetroots. This could make 6-phosphogluconic acid a potential biomarker for the consumption of these foods.
CAS Number921-62-0
Structure
Thumb
Synonyms
SynonymSource
6-Phospho-D-gluconateChEBI
6-Phospho-D-gluconic acidGenerator
6-PhosphogluconateGenerator
6-O-Phosphono-D-gluconic acidHMDB
6-p-GluconateHMDB
D-Gluconic acid 6-(dihydrogen phosphate)HMDB
D-Gluconic acid 6-phosphateHMDB
Gluconic acid-6-phosphateHMDB
Gluconate 6-phosphateHMDB
6-O-D-GluconateChEBI
6-O-D-Gluconic acidGenerator
6-O-ONO-D-Gluconic acidHMDB
6-O-phosphono-D-gluconic acidhmdb
6-OgluconateHMDB
6-Ogluconic acidHMDB
6-p-gluconatehmdb
6-phosphogluconatehmdb
6-phosphogluconic acidhmdb
D-Gluconic acid 6-(dihydrogen ate)HMDB
D-Gluconic acid 6-ateHMDB
Gluconic acid-6-ateHMDB
gluconic acid-6-phosphatehmdb
Predicted Properties
PropertyValueSource
Water Solubility20.7 g/LALOGPS
logP-2.3ALOGPS
logP-3.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area184.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.14 m³·mol⁻¹ChemAxon
Polarizability21.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H13O10P
IUPAC name(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid
InChI IdentifierInChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1
InChI KeyBIRSGZKFKXLSJQ-SQOUGZDYSA-N
Isomeric SMILESO[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
Average Molecular Weight276.1352
Monoisotopic Molecular Weight276.024633148
Classification
Description Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Gluconic_acid
  • Hexose monosaccharide
  • Monosaccharide phosphate
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Monoalkyl phosphate
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alkyl phosphate
  • Fatty acid
  • Alpha-hydroxy acid
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Hydroxy acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
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-MS6-Phosphogluconic acid, 5 TMS, GC-MS Spectrumsplash10-0uxu-0933000000-d0c837bb667abbae2ce0Spectrum
GC-MS6-Phosphogluconic acid, 7 TMS, GC-MS Spectrumsplash10-00ks-1978000000-c7702d284ad9f06bb5c0Spectrum
GC-MS6-Phosphogluconic acid, non-derivatized, GC-MS Spectrumsplash10-0uxu-0933000000-d0c837bb667abbae2ce0Spectrum
GC-MS6-Phosphogluconic acid, non-derivatized, GC-MS Spectrumsplash10-00ks-1978000000-c7702d284ad9f06bb5c0Spectrum
Predicted GC-MS6-Phosphogluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4j-9430000000-e4198ba354325082e116Spectrum
Predicted GC-MS6-Phosphogluconic acid, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-7192047000-e8fa0bd25a22fa6fd28bSpectrum
Predicted GC-MS6-Phosphogluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6-Phosphogluconic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dj-5090000000-a1b0f01abec0e4fb22c5Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b62Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff41Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d218Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cdSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d218Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f532Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e12603Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e1b81e634eb90448b9cdSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2590000000-53a3a79c2cc73c243e4eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6v-7920000000-e9b87a1b1cd046187a03Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-299a98a9b8ecad68997dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9830000000-f784c955d104bea3213fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-bffd36c521b6f41716d9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d27f7e55395c8a6e1547Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID82615
ChEMBL IDCHEMBL1230513
KEGG Compound IDC00345
Pubchem Compound ID91493
Pubchem Substance IDNot Available
ChEBI ID16863
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01316
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34686
KNApSAcK IDNot Available
HET ID6PG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID6-phosphogluconate
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
Enzymes
NameGene NameUniProt ID
6-phosphogluconolactonasePGLSO95336
6-phosphogluconate dehydrogenase, decarboxylatingPGDP52209
Probable gluconokinaseIDNKQ5T6J7
Pathways
NameSMPDB LinkKEGG Link
Pentose Phosphate PathwaySMP00031 map00030
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference