Bovine Metabolome Database: Showing metabocard for Glucose 1-phosphate (BMDB0001586)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (11) Show 11 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:50 UTC

Update Date

2020-06-04 20:50:42 UTC

BMDB ID

BMDB0001586

Secondary Accession Numbers

BMDB01586

Metabolite Identification

Common Name

Glucose 1-phosphate

Description

Galactose 1-phosphate, also known as delta-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. Galactose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose 1-phosphate exists in all living species, ranging from bacteria to humans. Galactose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate through its interaction with the enzyme galactose-1-phosphate uridylyltransferase. Furthermore, Galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. Finally, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is mediated by the enzyme galactose-1-phosphate uridylyltransferase. In cattle, galactose 1-phosphate is involved in a couple of metabolic pathways, which include the nucleotide sugars metabolism pathway and lactose synthesis pathway. Galactose 1-phosphate is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-O-Phosphono-D-glucopyranose	ChEBI
Cori ester	ChEBI
D-Glucose 1-phosphate	ChEBI
GLC-1-p	ChEBI
D-Glucose 1-phosphoric acid	Generator
Glucose 1-phosphoric acid	Generator
a-D-Glucopyranosyl phosphate	HMDB
a-D-Glucose 1-phosphate	HMDB
alpha-D-Glucopyranosyl phosphate	HMDB
alpha-D-Glucose 1-phosphate	HMDB
alpha-D-Glucose-1-phosphate	HMDB
alpha-delta-Glucopyranosyl phosphate	HMDB
alpha-delta-Glucose 1-phosphate	HMDB
alpha-delta-Glucose-1-phosphate	HMDB
D-Glucopyranose 1-phosphate	HMDB
D-Glucose-1-p	HMDB
D-Glucose-1-phosphate	HMDB
delta-Glucopyranose 1-phosphate	HMDB
delta-Glucose 1-phosphate	HMDB
delta-Glucose-1-p	HMDB
delta-Glucose-1-phosphate	HMDB
Glucose monophosphate	HMDB
Glucose-1-phosphate	HMDB
Glucose-1P	HMDB
Galactose 1-phosphoric acid	HMDB

Chemical Formula

C₆H₁₃O₉P

Average Molecular Weight

260.1358

Monoisotopic Molecular Weight

260.029718526

IUPAC Name

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

Traditional Name

glucose 1-phosphate

CAS Registry Number

59-56-3

SMILES

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

InChI Identifier

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

InChI Key

HXXFSFRBOHSIMQ-GASJEMHNSA-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.

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-glucose monophosphate (CHEBI:16077 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000.0 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	20.65 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9110000000-ee60e23a7f8053dae6d3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-003r-5591470000-4932aa0d35a53458633d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0a4i-0390000000-9e3307d6125b74ed8579	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-05mk-2960000000-4950cd68ef81b4267967	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0230-5970000000-4c2745937c6f87f89f17	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-03di-0090000000-3c372084bb61e1ef4257	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-0002-0090000000-90411431cffd98ebe09f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0002-0090000000-9f2b4a83b1e7bad0b54b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0002-0290000000-0701b77382bb89dff4e2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000j-0980000000-3f1ea14f9deeb0503ccb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-000i-0920000000-1563a20c1e81bd3e405b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-0f79-0960000000-861f86d1031c9d86f753	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000i-0009000000-89f3bc29378643fb7eb7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-000i-0109000000-cdd8143c3ba06849c689	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-05g0-0905000000-51b42ad0609cced943ea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-05fr-0900000000-6d206170422cec07547c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, positive	splash10-05fr-0900000000-96d8b3ec28a5f4f92dfd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-01b9-0509000000-83bba45a888d3e2c8b46	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-006t-9600000000-e6e68c22e3002384468f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-0a4i-0900000000-58fa2680157a4d69ead7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 18V, positive	splash10-00di-0911000000-611d985a6a959222f903	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9240000000-0a7885872856fe43526b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9240000000-b437590c213fb263989d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0532-9100000000-97504a02d14244b901cb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-9360000000-98c3aee1d36863dc12ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-92ad15ffc9eae3eed039	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfc211275bafe42581ae	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Fibroblasts
Longissimus Thoracis Muscle
Mammary Gland
Milk
Muscle
Semimembranosus Muscle
Urine

Pathways

Name	SMPDB/Pathwhiz	KEGG
Nucleotide Sugars Metabolism		Not Available
Glycolysis		Not Available
Gluconeogenesis		Not Available
Galactose Metabolism		Not Available
Lactose Synthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Longissimus Thoracis Muscle	Detected and Quantified	184 +/- 58 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23497994	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25087032	details
Milk	Detected and Quantified	52.60 +/- 27.92 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	3.844 uM	Not Specified	Not Specified	Normal	PMID: 13018287	details
Milk	Detected and Quantified	58 +/- 2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	43 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	43 +/- 11 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	55 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	55 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	58 +/- 2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	86.70 +/- 128.89 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	43 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	43 +/- 11 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	28.31 +/- 27.81 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Muscle	Detected and Quantified	363-1178 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 30744349	details
Muscle	Detected and Quantified	120 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 26437054	details
Semimembranosus Muscle	Detected and Quantified	175 +/- 48 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25599412	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001586

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001159

KNApSAcK ID

Not Available

Chemspider ID

388311

KEGG Compound ID

C00103

BioCyc ID

D-glucose-1-phosphates

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16077

References

Synthesis Reference

Weinhausel, Andreas; Nidetzky, Bernd; Kysela, Christian; Kulbe, Klaus D. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme and Microbial Technology (1995), 17(2), 140-6.

Material Safety Data Sheet (MSDS)

Not Available

General References

Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details

1. Alpha-1,4 glucan phosphorylase

General function:: Carbohydrate transport and metabolism
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:: PYGM
Uniprot ID:: B0JYK6
Molecular weight:: 97288.0

Enzyme Details

2. Glucose-6-phosphatase

General function:: Involved in glucose-6-phosphatase activity
Specific function:: Hydrolyzes glucose-6-phosphate to glucose in the endoplasmic reticulum. Forms with the glucose-6-phosphate transporter (SLC37A4/G6PT) the complex responsible for glucose production through glycogenolysis and gluconeogenesis. Hence, it is the key enzyme in homeostatic regulation of blood glucose levels (By similarity).
Gene Name:: G6PC
Uniprot ID:: Q29RU6
Molecular weight:: 40827.0

Reactions

Glucose 1-phosphate + Water → D-Glucose + Hydrogen phosphate	details

Enzyme Details

3. Phosphoglucomutase-1

General function:: Carbohydrate transport and metabolism
Specific function:: This enzyme participates in both the breakdown and synthesis of glucose.
Gene Name:: PGM1
Uniprot ID:: Q08DP0
Molecular weight:: 61589.0

Reactions

Glucose 1-phosphate → Glucose 6-phosphate	details
Uridine diphosphate glucose → Glucose 1-phosphate	details

Enzyme Details

4. Galactose-1-phosphate uridylyltransferase

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: GALT
Uniprot ID:: Q0V7N7
Molecular weight:: 37812.0

Enzyme Details

5. Galactose-1-phosphate uridylyltransferase

General function:: Energy production and conversion
Specific function:: Not Available
Gene Name:: GALT
Uniprot ID:: Q58CX1
Molecular weight:: 41288.0

Reactions

Uridine diphosphategalactose + Glucose 1-phosphate → Uridine diphosphate glucose + Galactose 1-phosphate	details
Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphate	details
Uridine diphosphategalactose + Glucose 1-phosphate → Galactose 1-phosphate + Uridine diphosphate glucose	details

Enzyme Details

6. UTP--glucose-1-phosphate uridylyltransferase

General function:: Involved in UTP:glucose-1-phosphate uridylyltransferase
Specific function:: Plays a central role as a glucosyl donor in cellular metabolic pathways.
Gene Name:: UGP2
Uniprot ID:: Q07130
Molecular weight:: 56903.0

Reactions

Glucose 1-phosphate + Uridine triphosphate → Uridine diphosphate glucose + Pyrophosphate	details
Uridine diphosphate glucose + Pyrophosphate → Glucose 1-phosphate + Uridine triphosphate	details

Enzyme Details

7. Glycogen phosphorylase, brain form

General function:: Carbohydrate transport and metabolism
Specific function:: Glycogen phosphorylase that regulates glycogen mobilization. Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:: PYGB
Uniprot ID:: Q3B7M9
Molecular weight:: 96340.0

Enzyme Details

8. Glycogen phosphorylase, liver form

General function:: Carbohydrate transport and metabolism
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties (By similarity).
Gene Name:: PYGL
Uniprot ID:: Q0VCM4
Molecular weight:: 97456.0

Reactions

Glycogen + Hydrogen phosphate → Amylose + Glucose 1-phosphate	details

Enzyme Details

9. Glycogen phosphorylase, muscle form

General function:: Carbohydrate transport and metabolism
Specific function:: Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:: PYGM
Uniprot ID:: P79334
Molecular weight:: 97293.0

Enzyme Details

10. PGM2L1 protein

General function:: Not Available
Specific function:: Not Available
Gene Name:: PGM2L1
Uniprot ID:: A5PKH8
Molecular weight:: 70419.0

Reactions

Glucose 1-phosphate + Glyceric acid 1,3-biphosphate → Alpha-D-Glucose 1,6-bisphosphate + 3-Phosphoglyceric acid	details

Enzyme Details

11. UDP-glucose 4-epimerase

General function:: Not Available
Specific function:: Catalyzes two distinct but analogous reactions: the reversible epimerization of UDP-glucose to UDP-galactose and the reversible epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine. The reaction with UDP-Gal plays a critical role in the Leloir pathway of galactose catabolism in which galactose is converted to the glycolytic intermediate glucose 6-phosphate. It contributes to the catabolism of dietary galactose and enables the endogenous biosynthesis of both UDP-Gal and UDP-GalNAc when exogenous sources are limited. Both UDP-sugar interconversions are important in the synthesis of glycoproteins and glycolipids.
Gene Name:: GALE
Uniprot ID:: Q3T105
Molecular weight:: 38254.0

Reactions

Uridine diphosphate glucose + Galactose 1-phosphate → Uridine diphosphategalactose + Glucose 1-phosphate	details

Showing metabocard for Glucose 1-phosphate (BMDB0001586)

Structure for BMDB0001586 (Glucose 1-phosphate)

Enzymes

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