ECMDB: 6-Phosphogluconic acid (ECMDB01316) (M2MDB000336)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (872)

Record Information

Version

2.0

Creation Date

2012-05-31 13:49:48 -0600

Update Date

2015-09-13 12:56:10 -0600

Secondary Accession Numbers

ECMDB01316

Identification

Name:

6-Phosphogluconic acid

Description

6-Phosphogluconic acid is an intermediate in the Pentose phosphate pathway (KEGG)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

6-O-Phosphono-D-gluconate
6-O-Phosphono-D-gluconic acid
6-p Gluconate
6-p Gluconic acid
6-p-Gluconate
6-p-Gluconic acid
6-PG
6-Phospho gluconate
6-Phospho gluconic acid
6-Phospho-D-gluconate
6-Phospho-D-gluconic acid
6-Phosphogluconate
6-Phosphogluconic acid
D-Gluconate 6-(dihydrogen phosphate)
D-Gluconate 6-phosphate
D-Gluconic acid 6-(dihydrogen phosphate)
D-Gluconic acid 6-(dihydrogen phosphoric acid)
D-Gluconic acid 6-phosphate
D-Gluconic acid 6-phosphoric acid
Gluconate-6-phosphate
Gluconic acid-6-phosphate
Gluconic acid-6-phosphoric acid

Chemical Formula:

C₆H₁₃O₁₀P

Weight:

Average: 276.1352
Monoisotopic: 276.024633148

InChI Key:

BIRSGZKFKXLSJQ-SQOUGZDYSA-N

InChI:

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

CAS number:

921-62-0

IUPAC Name:

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

Traditional IUPAC Name:

6-phosphogluconic acid

SMILES:

O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide 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 Framework

Aliphatic acyclic compounds

External Descriptors

gluconic acid phosphate (CHEBI:48928 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	20.7 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.49	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	184.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	49.14 m³·mol⁻¹	ChemAxon
Polarizability	21.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Glutathione metabolism	PW000833
Pentose Phosphate	PW000893

KEGG Pathways:

Glutathione metabolism ec00480
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Pentose phosphate pathway ec00030

EcoCyc Pathways:

D-gluconate degradation GLUCONSUPER-PWY
Entner-Doudoroff pathway I ENTNER-DOUDOROFF-PWY
L-idonate degradation IDNCAT-PWY
pentose phosphate pathway (oxidative branch) OXIDATIVEPENT-PWY
superpathway of glycolysis and Entner-Doudoroff GLYCOLYSIS-E-D

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
310± 0 uM	W3110	4.0 g/L Na2SO4; 5.36 g/L (NH4)2SO4; 1.0 g/L NH4Cl; 7.3 g/L K2HPO4; 1.8 g/L NaH2PO4 H2O; 12.0 g/L (NH4)2-H-citrate; 4.0 mL/L MgSO4 (1 M); 6.0 mL/L trace element solution; 0.02 g/L thiamine, 20 g/L glucose	Mid Log Phase	Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h	37 oC	Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.
450± 32 uM	K12	0.2 g/L NH4Cl, 2.0 g/L (NH4)2SO4, 3.25 g/L KH2PO4, 2.5 g/L K2HPO4, 1.5 g/L NaH2PO4, 0.5 g/L MgSO4; trace substances: 10 mg/L CaCl2, 0.5 mg/L ZnSO4, 0.25 mg/L CuCl2, 0.25 mg/L MnSO4, 0.175 mg/L CoCl2, 0.125 mg/L H3BO3, 2.5 mg/L AlCl3, 0.5 mg/L Na2MoO4, 10	Stationary Phase, glucose limited	Bioreactor, pH controlled, aerated, dilution rate=0.125 L/h	37 oC	PMID: 11488613
380± 70 uM	BW25113	M9 Minimal Media, 4 g/L Glucose	Mid-Log Phase	Bioreactor, pH controlled, O2 controlled, dilution rate: 0.2/h	37 oC	PMID: 15158257
3770± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
400± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
193± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-0uxu-0933000000-d0c837bb667abbae2ce0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (7 TMS)	splash10-00ks-1978000000-c7702d284ad9f06bb5c0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0uxu-0933000000-d0c837bb667abbae2ce0	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00ks-1978000000-c7702d284ad9f06bb5c0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9430000000-e4198ba354325082e116	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-00dl-7192047000-e8fa0bd25a22fa6fd28b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00dj-5090000000-a1b0f01abec0e4fb22c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-002b-9000000000-780e6dc35ed33dde8b62	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-004i-9000000000-df8e5979c41c127eff41	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00b9-0495110000-a9d468f24ea04c2dd0d2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-9100000000-25ef4bb1cdb69b6418ce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4j-5090000000-6db5e52f38f29e35f42a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0090000000-b6ed9e59bd4492f4b5ce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0190000000-50702b7e8f4b7289d218	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004j-9260000000-e356e1c75aa70d0065f9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-002b-9100000000-5be967e173f74d688dc2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004j-9000000000-1c5eda88c214ef66d7b6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-e1b81e634eb90448b9cd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0090000000-50702b7e8f4b7289d218	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-9260000000-20df41bde9cbb406f532	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-002b-9100000000-56434d8c214a22e12603	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-9000000000-1c5eda88c214ef66d7b6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-e1b81e634eb90448b9cd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9100000000-25ef4bb1cdb69b6418ce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4j-5090000000-6db5e52f38f29e35f42a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0090000000-b6ed9e59bd4492f4b5ce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-002b-9100000000-15a83e588180be4c0664	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-3d9937a328c6aa73fe8a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004j-7190000000-26e8b7b5ea3ee85cbb61	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-002b-9100000000-39b6ad01fb7aa0ecbb1a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 19V, positive	splash10-01ow-3390000000-1a67f265724b65046d12	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Ahmed N, Weidemann MJ: Purine metabolism in promyelocytic HL60 and dimethylsulphoxide-differentiated HL60 cells. Leuk Res. 1994 Jun;18(6):441-51. Pubmed: 8207962
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Buchholz, A., Takors, R., Wandrey, C. (2001). "Quantification of intracellular metabolites in Escherichia coli K12 using liquid chromatographic-electrospray ionization tandem mass spectrometric techniques." Anal Biochem 295:129-137. Pubmed: 11488613
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
Harada S: Isoelectrofocusing in acetate membrane: the method and application. Clin Chim Acta. 1975 Sep 16;63(3):275-83. Pubmed: 240520
Harmon CS, Phizackerley PJ: Glycogen metabolism in psoriatic epidermis and in regenerating epidermis. Clin Sci (Lond). 1984 Sep;67(3):291-8. Pubmed: 6432401
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
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
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(1):18. Pubmed: 15882454
Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.
Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23. Pubmed: 15158257
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
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. Pubmed: 19212411
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
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	16863
HMDB ID	HMDB01316
Pubchem Compound ID	91493
Kegg ID	C00345
ChemSpider ID	82615
Wikipedia	6-phosphogluconate
BioCyc ID	CPD-2961
EcoCyc ID	CPD-2961
Ligand Expo	6PG

Enzymes

Protein Details

1. 6-phosphogluconate dehydrogenase, decarboxylating

General function:: Involved in oxidation-reduction process
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:: gnd
Uniprot ID:: P00350
Molecular weight:: 51481

Reactions

6-phospho-D-gluconate + NADP(+) = D-ribulose 5-phosphate + CO(2) + NADPH.

Protein Details

2. Phosphogluconate dehydratase

General function:: Involved in phosphogluconate dehydratase activity
Specific function:: 6-phospho-D-gluconate = 2-dehydro-3-deoxy-6- phospho-D-gluconate + H(2)O
Gene Name:: edd
Uniprot ID:: P0ADF6
Molecular weight:: 64639

Reactions

6-phospho-D-gluconate = 2-dehydro-3-deoxy-6-phospho-D-gluconate + H(2)O.

Protein Details

3. Thermosensitive gluconokinase

General function:: Involved in shikimate kinase activity
Specific function:: ATP + D-gluconate = ADP + 6-phospho-D- gluconate
Gene Name:: idnK
Uniprot ID:: P39208
Molecular weight:: 21004

Reactions

ATP + D-gluconate = ADP + 6-phospho-D-gluconate.

Protein Details

4. Thermoresistant gluconokinase

General function:: Involved in shikimate kinase activity
Specific function:: ATP + D-gluconate = ADP + 6-phospho-D- gluconate
Gene Name:: gntK
Uniprot ID:: P46859
Molecular weight:: 19543

Reactions

ATP + D-gluconate = ADP + 6-phospho-D-gluconate.

Protein Details

5. 6-phosphogluconolactonase

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: Catalyzes the hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate
Gene Name:: pgl
Uniprot ID:: P52697
Molecular weight:: 36308

Reactions

6-phospho-D-glucono-1,5-lactone + H(2)O = 6-phospho-D-gluconate.

6-Phosphogluconic acid (ECMDB01316) (M2MDB000336)

Structure for #<Compound:0xa8036d8c>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions