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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:53 UTC
HMDB IDHMDB0001316
Secondary Accession Numbers
  • HMDB01316
Metabolite Identification
Common Name6-Phosphogluconic acid
DescriptionIntermediate in the Pentose phosphate pathway (KEGG).
Structure
Data?1563860693
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0uxu-0933000000-d0c837bb667abbae2ce0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (7 TMS)splash10-00ks-1978000000-c7702d284ad9f06bb5c0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uxu-0933000000-d0c837bb667abbae2ce0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ks-1978000000-c7702d284ad9f06bb5c0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9430000000-e4198ba354325082e116JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00dl-7192047000-e8fa0bd25a22fa6fd28bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dj-5090000000-a1b0f01abec0e4fb22c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b62JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff41JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d218JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d218JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f532JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e12603JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e1b81e634eb90448b9cdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2590000000-53a3a79c2cc73c243e4eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6v-7920000000-e9b87a1b1cd046187a03JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9400000000-299a98a9b8ecad68997dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9830000000-f784c955d104bea3213fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-bffd36c521b6f41716d9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d27f7e55395c8a6e1547JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified2720 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.117 +/- 0.228 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.171 +/- 0.231 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.253 +/- 0.218 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.557 +/- 0.537 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
Associated OMIM IDs
DrugBank IDDB02076
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022550
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)Download (PDF)
General References
  1. Chen SH, Karp LE, Scott CR, Chen W: Use of genetic markers to certify fetal origin of cultured amniotic fluid cells. Hum Genet. 1981;57(3):323-4. [PubMed:6454643 ]
  2. Schwerd W, Fehrer HD: [The detection of inherited enzyme polymorphism in semen (author's transl)]. Z Rechtsmed. 1979 Jul 17;83(2):129-38. [PubMed:494813 ]
  3. Ahmed N, Weidemann MJ: Purine metabolism in promyelocytic HL60 and dimethylsulphoxide-differentiated HL60 cells. Leuk Res. 1994 Jun;18(6):441-51. [PubMed:8207962 ]
  4. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
  5. Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. Epub 2005 Jan 23. [PubMed:16055050 ]
  6. Moghetti P, Bonora E, Cigolini M, Querena M, Cacciatori V, Muggeo M: Enzymatic activities related to intermediary metabolism of glucose in circulating mononuclear cells from obese humans: relationship to enzyme activity in adipose tissue. Enzyme. 1990;43(1):26-32. [PubMed:2141817 ]
  7. Harmon CS, Phizackerley PJ: Glycogen metabolism in psoriatic epidermis and in regenerating epidermis. Clin Sci (Lond). 1984 Sep;67(3):291-8. [PubMed:6432401 ]
  8. Harada S: Isoelectrofocusing in acetate membrane: the method and application. Clin Chim Acta. 1975 Sep 16;63(3):275-83. [PubMed:240520 ]
  9. Swierczynski J, Goyke E, Wach L, Pankiewicz A, Kochan Z, Adamonis W, Sledzinski Z, Aleksandrowicz Z: Comparative study of the lipogenic potential of human and rat adipose tissue. Metabolism. 2000 May;49(5):594-9. [PubMed:10831168 ]
  10. 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. [PubMed:19212411 ]

Enzymes

General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:
PGLS
Uniprot ID:
O95336
Molecular weight:
27546.495
Reactions
6-phospho-D-glucono-1,5-lactone + Water → 6-Phosphogluconic aciddetails
6-Phosphonoglucono-D-lactone + Water → 6-Phosphogluconic aciddetails
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Oxidizes glucose-6-phosphate and glucose, as well as other hexose-6-phosphates.
Gene Name:
H6PD
Uniprot ID:
O95479
Molecular weight:
88891.99
Reactions
6-phospho-D-glucono-1,5-lactone + Water → 6-Phosphogluconic aciddetails
6-Phosphonoglucono-D-lactone + Water → 6-Phosphogluconic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
Gene Name:
PGD
Uniprot ID:
P52209
Molecular weight:
53139.56
Reactions
6-Phosphogluconic acid + NADP → D-Ribulose 5-phosphate + CO(2) + NADPHdetails
6-Phosphogluconic acid + NADP → D-Ribulose 5-phosphate + Carbon dioxide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
PGD
Uniprot ID:
A9Z1X1
Molecular weight:
32311.5
General function:
Involved in shikimate kinase activity
Specific function:
Not Available
Gene Name:
IDNK
Uniprot ID:
Q5T6J7
Molecular weight:
20577.63
Reactions
Adenosine triphosphate + Gluconic acid → ADP + 6-Phosphogluconic aciddetails