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Showing Compound 6-Phosphogluconic acid (FDB022550)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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-a1b0f01abec0e4fb22c52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b622012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff412012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d2182012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d2182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f5322017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e126032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-1c5eda88c214ef66d7b62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e1b81e634eb90448b9cd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-002b-9100000000-15a83e588180be4c06642021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3d9937a328c6aa73fe8a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004j-7190000000-26e8b7b5ea3ee85cbb612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-002b-9100000000-39b6ad01fb7aa0ecbb1a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-01ow-3390000000-1a67f265724b65046d122020-07-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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