6-Phosphogluconic acid (YMDB00218)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

Identification

YMDB ID

YMDB00218

Name

6-Phosphogluconic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

6-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 an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphogluconic acid exists in all living species, ranging from bacteria to humans.

Structure

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

Synonyms

6-O-phosphono-D-gluconic acid
6-p-gluconate
6-Phospho-D-gluconate
6-Phospho-D-gluconic acid
6-phosphogluconate
6-phosphogluconic acid
d-gluconate 6-phosphate
D-Gluconic acid 6-(dihydrogen phosphate)
D-Gluconic acid 6-phosphate
gluconic acid-6-phosphate
Gluconate 6-phosphate

CAS number

921-62-0

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

IUPAC Name

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

Traditional IUPAC Name

6-phosphogluconic acid

Chemical Formula

C₆H₁₃O₁₀P

SMILES

[H]OC(=O)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Pentose phosphate pathway

ec00030

SMPDB Reactions

Not Available

KEGG Reactions

water + 6-Phosphonoglucono-D-lactone → 6-Phosphogluconic acid + hydron

6-Phosphogluconic acid + NADP → Carbon dioxide + NADPH + D-ribulose 5-phosphate

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
200 ± 100 µM	Minimal medium supplemented with ammonia salts and (glucose or galactose)	aerobic;growing cells	Baker's yeast	PMID: 4578278
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

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

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
KAWADA, M., KAGAWA, Y., TAKIGUCHI, H., SHIMAZONO, N. (1962). "Purification of 6-phosphogluconolactonase from rat liver and yeast; its separation from gluconolactonase." Biochim Biophys Acta 57:404-407.14454532
Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	48928
HMDB ID	HMDB01316
Pubchem Compound ID	91493
Kegg ID	C00345
ChemSpider ID	82615
FOODB ID	FDB030611
Wikipedia	6-Phosphogluconic_acid
BioCyc ID	CPD-2961

Enzymes

Protein Details

1. Probable gluconokinase

General function:: Involved in ATP binding
Specific function:: ATP + D-gluconate = ADP + 6-phospho-D- gluconate
Gene Name:: Not Available
Uniprot ID:: Q03786
Molecular weight:: 22174.5

Reactions

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

Protein Details

2. 6-phosphogluconolactonase 4

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: Hydrolysis of 6-phosphogluconolactone to 6- phosphogluconate
Gene Name:: SOL4
Uniprot ID:: P53315
Molecular weight:: 28447.5

Reactions

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

Protein Details

3. 6-phosphogluconolactonase-like protein 1

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: May be involved in regulation of tRNA subcellular distribution
Gene Name:: SOL1
Uniprot ID:: P50278
Molecular weight:: 35652.19922

Reactions

Protein Details

4. 6-phosphogluconolactonase-like protein 2

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: May be involved in regulation of tRNA subcellular distribution
Gene Name:: SOL2
Uniprot ID:: P37262
Molecular weight:: 34500.89844

Reactions

Protein Details

5. 6-phosphogluconate dehydrogenase, decarboxylating 1

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
Gene Name:: GND1
Uniprot ID:: P38720
Molecular weight:: 53542.69922

Reactions

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

Protein Details

6. 6-phosphogluconate dehydrogenase, decarboxylating 2

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
Gene Name:: GND2
Uniprot ID:: P53319
Molecular weight:: 53922.30078

Reactions

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

Protein Details

7. 6-phosphogluconolactonase 3

General function:: Involved in 6-phosphogluconolactonase activity
Specific function:: Hydrolysis of 6-phosphogluconolactone to 6- phosphogluconate
Gene Name:: SOL3
Uniprot ID:: P38858
Molecular weight:: 27784.19922

Reactions

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

Structure for #<Compound:0xaadbeac0>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions