alpha-D-glucose 1-phosphate (YMDB00970)

Identification

YMDB ID

YMDB00970

Name

alpha-D-glucose 1-phosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

α-D-Glucose 1-phosphate, also known as alpha-D-glucose-1-phosphate or cori ester, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. α-D-Glucose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). α-D-Glucose 1-phosphate exists in both E. coli (prokaryote) and yeast (eukaryote).

Structure

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

Synonyms

1-O-phosphono-alpha-D-glucopyranose
a-D-Glucopyranosyl phosphate
a-D-Glucose 1-phosphate
alpha-D-Glucopyranosyl phosphate
alpha-D-Glucose 1-phosphate
alpha-d-glucose-1-phosphate
alpha-delta-Glucopyranosyl phosphate
alpha-delta-Glucose 1-phosphate
alpha-delta-glucose-1-phosphate
cori ester
D-Glucopyranose 1-phosphate
D-glucose 1-phosphate
D-Glucose alpha-1-phosphate
D-glucose-1-P
D-Glucose-1-phosphate
delta-Glucopyranose 1-phosphate
delta-glucose 1-phosphate
delta-glucose-1-P
delta-Glucose-1-phosphate
glucose 1-phosphate
Glucose 1-phosphic acid
Glucose monophosphate
Glucose-1-phosphate
glucose-1P
1-O-Phosphono-a-D-glucopyranose
1-O-Phosphono-α-D-glucopyranose
Glucose 1-phosphoric acid
a-D-Glucopyranosyl phosphoric acid
alpha-D-Glucopyranosyl phosphoric acid
α-D-Glucopyranosyl phosphate
α-D-Glucopyranosyl phosphoric acid
a-D-Glucose-1-phosphate
a-D-Glucose-1-phosphoric acid
alpha-D-Glucose-1-phosphoric acid
α-D-Glucose-1-phosphate
α-D-Glucose-1-phosphoric acid
D-Glucose 1-phosphoric acid
D-Glucose a-1-phosphate
D-Glucose a-1-phosphoric acid
D-Glucose alpha-1-phosphoric acid
D-Glucose α-1-phosphate
D-Glucose α-1-phosphoric acid
alpha-Glucose-1-phosphate
a-D-Glucose 1-phosphoric acid
alpha-D-Glucose 1-phosphoric acid
α-D-Glucose 1-phosphoric acid
α-D-Glucose 1-phosphate

CAS number

59-56-3

Weight

Average: 260.1358
Monoisotopic: 260.029718526

InChI Key

HXXFSFRBOHSIMQ-VFUOTHLCSA-N

InChI

InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1

IUPAC Name

{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional IUPAC Name

α-D-glucose 1-phosphate

Chemical Formula

C₆H₁₃O₉P

SMILES

OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

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

Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Alkyl phosphate
Phosphoric acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucopyranose 1-phosphate (CHEBI:29042 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	1000 mg/mL [MERCK INDEX (1996); extremely soluble]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	32.3 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.1	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol⁻¹	ChemAxon
Polarizability	20.72 Å³	ChemAxon
Number of Rings	1	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

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Amino sugar and nucleotide sugar metabolism	PW002413
Ethanol fermentation	PW002448
Glycolysis I	PW002386
Leloir Pathway	PW002397
Starch and sucrose metabolism	PW002481

KEGG Pathways

Amino sugar and nucleotide sugar metabolism	ec00520
Galactose metabolism	ec00052
Glycolysis / Gluconeogenesis	ec00010
Pentose and glucuronate interconversions	ec00040
Starch and sucrose metabolism	ec00500

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0890000000-cb800147fb5e99a510e7	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9110000000-ee60e23a7f8053dae6d3	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0090000000-2a3b56296e3be19cb31e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-5190000000-fdc51a7b0fd975e56650	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-69de35d5ce6872252869	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-9963fa05cb28ee4e9750	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-817af0fa07de830dfcf8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0090000000-2322457ec511bd92510d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-5090000000-d986f523677b1a7addcd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-ce71459726865b116c97	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-41baf1958afa8e1bca49	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-bfea8e3efab209c2697e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-1090000000-8e32630bfab3f0ed6178	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0a4i-0090000000-0c85f2f24f79558bd95e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9030000000-cc7fbcb760461482d91a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9100000000-41a1f7e48ed2619c083c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9100000000-7c0c1db3eeeec90afc60	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-1f32b398f51ac98aaa87	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-2785b12981c99944620a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-004i-9000000000-abfc53ea34b8f04f9f65	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9200000000-1e94374a7c4c5c6c58ea	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9240000000-0a7885872856fe43526b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9240000000-b437590c213fb263989d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0532-9100000000-97504a02d14244b901cb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-9360000000-98c3aee1d36863dc12ab	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-92ad15ffc9eae3eed039	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfc211275bafe42581ae	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:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Daran, J. M., Dallies, N., Thines-Sempoux, D., Paquet, V., Francois, J. (1995). "Genetic and biochemical characterization of the UGP1 gene encoding the UDP-glucose pyrophosphorylase from Saccharomyces cerevisiae." Eur J Biochem 233:520-530.7588797
Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	29042
HMDB ID	HMDB01586
Pubchem Compound ID	65533
Kegg ID	C00103
ChemSpider ID	24604707
FOODB ID	FDB021830
Wikipedia	Glucose_1-phosphate
BioCyc ID	GLC-1-P

Enzymes

Protein Details

1. Galactose-1-phosphate uridylyltransferase

General function:: Involved in UDP-glucose:hexose-1-phosphate uridylyltransferase activity
Specific function:: UDP-glucose + alpha-D-galactose 1-phosphate = alpha-D-glucose 1-phosphate + UDP-galactose
Gene Name:: GAL7
Uniprot ID:: P08431
Molecular weight:: 42384.69922

Reactions

UDP-glucose + alpha-D-galactose 1-phosphate → alpha-D-glucose 1-phosphate + UDP-galactose.

Protein Details

2. Probable UTP--glucose-1-phosphate uridylyltransferase

General function:: Involved in nucleotidyltransferase activity
Specific function:: Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:: Not Available
Uniprot ID:: P38709
Molecular weight:: 55999.80078

Reactions

UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.

Protein Details

3. UTP--glucose-1-phosphate uridylyltransferase

General function:: Involved in nucleotidyltransferase activity
Specific function:: Plays a central role as a glucosyl donor in cellular metabolic pathways
Gene Name:: UGP1
Uniprot ID:: P32861
Molecular weight:: 55987.39844

Reactions

UTP + alpha-D-glucose 1-phosphate → diphosphate + UDP-glucose.

Structure for #<Compound:0xb0280298>

Enzymes

Reactions

Reactions

Reactions