Sat. Aug 2nd, 2025

6-Phosphogluconic acid

By rofalproject
Common Name

6-Phosphogluconic acid Description

Intermediate in the Pentose phosphate pathway (KEGG). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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-phosphateMeSH

Chemical Formlia

C6H13O10P Average Molecliar Weight

276.1352 Monoisotopic Molecliar Weight

276.024633148 IUPAC Name

(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid Traditional Name

6-phosphogluconic acid CAS Registry Number

921-62-0 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 Key

BIRSGZKFKXLSJQ-SQOUGZDYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds Direct Parent

Monosaccharide phosphates Alternative Parents

  • Hexoses
  • Medium-chain hydroxy acids and derivatives
  • Medium-chain fatty acids
  • Sugar acids and derivatives
  • Monoalkyl phosphates
  • Hydroxy fatty acids
  • Beta hydroxy acids and derivatives
  • Alpha hydroxy acids and derivatives
  • Secondary alcohols
  • Polyols
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • gluconic acid phosphate (CHEBI:48928 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Endoplasmic reticlium

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility20.7 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count7ChemAxon Refractivity49.14 m3·mol-1ChemAxon Polarizability21.6 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-MS (5 TMS)splash10-0uxu-0933000000-d0c837bb667abbae2ce0View in MoNA GC-MS

    GC-MS Spectrum – GC-MS (7 TMS)splash10-00ks-1978000000-c7702d284ad9f06bb5c0View in MoNA Predicted GC-MS

    Predicted GC-MS Spectrum – GC-MSNot Available LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-00dj-5090000000-a1b0f01abec0e4fb22c5View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-002b-9000000000-780e6dc35ed33dde8b62View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-004i-9000000000-df8e5979c41c127eff41View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00b9-0495110000-a9d468f24ea04c2dd0d2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-9100000000-25ef4bb1cdb69b6418ceView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4j-5090000000-6db5e52f38f29e35f42aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0090000000-b6ed9e59bd4492f4b5ceView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0190000000-50702b7e8f4b7289d218View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004j-9260000000-e356e1c75aa70d0065f9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-002b-9100000000-5be967e173f74d688dc2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004j-9000000000-1c5eda88c214ef66d7b6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-e1b81e634eb90448b9cdView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-004i-0090000000-50702b7e8f4b7289d218View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-004j-9260000000-20df41bde9cbb406f532View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , negativesplash10-002b-9100000000-56434d8c214a22e12603View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 2D NMR

    [1H,1H] 2D NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Endoplasmic reticlium

    • Biofluid Locations

  • Blood
  • Cellliar Cytoplasm
  • Saliva

    • Tissue Location

  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Prostate

    • Pathways

    Name SMPDB Link KEGG Link Glucose-6-phosphate dehydrogenase deficiencySMP00518Not Available Pentose Phosphate PathwaySMP00031map00030 Ribose-5-phosphate isomerase deficiencySMP00519Not Available Transaldolase deficiencySMP00520Not Available Warburg EffectSMP00654Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details Cellliar CytoplasmDetected and Quantified2720 uMAdlit (>18 years old)BothNormal

  • 15882454

    • details SalivaDetected and Quantified0.117 +/- 0.228 uMAdlit (>18 years old)Not Specified

    Normal

  • Sugimoto et al. (…

    • details SalivaDetected and Quantified0.171 +/- 0.231 uMAdlit (>18 years old)Female

    Normal

  • Sugimoto et al. (…

    • details SalivaDetected and Quantified0.253 +/- 0.218 uMAdlit (>18 years old)Not Specified

    Normal

  • Sugimoto et al. (…

    • details SalivaDetected and Quantified0.557 +/- 0.537 uMAdlit (>18 years old)Male

    Normal

  • Sugimoto et al. (…

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected but not Quantified Adlit (>18 years old)BothColorectal cancer

  • 25105552

    • details

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB022550 KNApSAcK ID

    Not Available Chemspider ID

    82615 KEGG Compound ID

    C00345 BioCyc ID

    CPD-2961 BiGG ID

    34686 Wikipedia Link

    6-phosphogluconate NuGOwiki Link

    HMDB01316 Metagene Link

    HMDB01316 METLIN ID

    367 PubChem Compound

    91493 PDB ID

    6PG ChEBI ID

    48928

    Product: Fmoc-Val-Cit-PAB-MMAE

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. 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 ]
    2. 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 ]
    3. 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 ]
    4. 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 ]
    5. Schwerd W, Fehrer HD: [The detection of inherited enzyme polymorphism in semen (authors transl)]. Z Rechtsmed. 1979 Jul 17;83(2):129-38. [PubMed:494813 ]
    6. Ahmed N, Weidemann MJ: Purine metabolism in promyelocytic HL60 and dimethylsulphoxide-differentiated HL60 cells. Leuk Res. 1994 Jun;18(6):441-51. [PubMed:8207962 ]
    7. 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 ]
    8. Harmon CS, Phizackerley PJ: Glycogen metabolism in psoriatic epidermis and in regenerating epidermis. Clin Sci (Lond). 1984 Sep;67(3):291-8. [PubMed:6432401 ]
    9. Harada S: Isoelectrofocusing in acetate membrane: the method and application. Clin Chim Acta. 1975 Sep 16;63(3):275-83. [PubMed:240520 ]
    10. 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 ]

    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 acid details 6-Phosphonoglucono-D-lactone + Water → 6-Phosphogluconic acid details
    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 acid details 6-Phosphonoglucono-D-lactone + Water → 6-Phosphogluconic acid details
    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) + NADPH details 6-Phosphogluconic acid + NADP → D-Ribulose 5-phosphate + Carbon dioxide + NADPH + Hydrogen Ion details
    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 acid details

    PMID: 19893758

    By rofalproject

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