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Record Information
Version1.0
Creation Date2016-09-30 22:44:02 UTC
Update Date2020-05-21 16:27:10 UTC
BMDB IDBMDB0001316
Secondary Accession Numbers
  • BMDB01316
Metabolite Identification
Common 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. 6-Phosphogluconic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphogluconic acid exists in all living species, ranging from bacteria to humans. 6-Phosphogluconic acid can be biosynthesized from gluconolactone and water; which is catalyzed by the enzyme 6-phosphogluconolactonase. In cattle, 6-phosphogluconic acid is involved in the metabolic pathway called the pentose phosphate pathway.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC6H13O10P
Average Molecular Weight276.1352
Monoisotopic Molecular Weight276.024633148
IUPAC Name(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid
Traditional Name6-phosphogluconic acid
CAS Registry Number921-62-0
SMILES
O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0uxu-0933000000-d0c837bb667abbae2ce0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-00ks-1978000000-c7702d284ad9f06bb5c0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uxu-0933000000-d0c837bb667abbae2ce0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ks-1978000000-c7702d284ad9f06bb5c0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9430000000-e4198ba354325082e116View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00dl-7192047000-e8fa0bd25a22fa6fd28bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dj-5090000000-a1b0f01abec0e4fb22c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d218View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d218View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f532View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e12603View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e1b81e634eb90448b9cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-002b-9100000000-15a83e588180be4c0664View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3d9937a328c6aa73fe8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004j-7190000000-26e8b7b5ea3ee85cbb61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-002b-9100000000-39b6ad01fb7aa0ecbb1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 19V, positivesplash10-01ow-3390000000-1a67f265724b65046d12View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen Locations
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0001316
DrugBank IDDB02076
Phenol Explorer Compound IDNot Available
FooDB IDFDB030611
KNApSAcK IDC00007481
Chemspider ID82615
KEGG Compound IDC00345
BioCyc IDCPD-2961
BiGG ID34686
Wikipedia Link6-Phosphogluconic_acid
METLIN ID367
PubChem Compound91493
PDB IDNot Available
ChEBI ID48928
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH.
Gene Name:
PGD
Uniprot ID:
Q3ZCI4
Molecular weight:
53077.0
General function:
Carbohydrate transport and metabolism
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:
PGLS
Uniprot ID:
Q2TBQ8
Molecular weight:
27547.0
Reactions
Gluconolactone + Water → 6-Phosphogluconic aciddetails
6-Phosphonoglucono-D-lactone + Water → 6-Phosphogluconic acid + Hydrogendetails