Human Metabolome Database Version 3.5

Showing metabocard for Beta-D-Glucose 6-phosphate (HMDB03498)

Record Information
Version 3.5
Creation Date 2006-08-12 16:03:45 -0600
Update Date 2013-02-08 17:12:36 -0700
HMDB ID HMDB03498
Secondary Accession Numbers None
Metabolite Identification
Common Name Beta-D-Glucose 6-phosphate
Description Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen, especially if blood glucose levels are high.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. beta-D-Glucose 6-(dihydrogen phosphate)
  2. beta-D-Glucose 6-phosphate
Chemical Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
IUPAC Name {[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number Not Available
SMILES O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1
InChI Key NBSCHQHZLSJFNQ-VFUOTHLCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • D-glucopyranose 6-phosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxane
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Hexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -3.643 Not Available
Predicted Properties
Property Value Source
Water Solubility 31.4 g/L ALOGPS
LogP -2.06 ALOGPS
LogP -3.1 ChemAxon
LogS -0.92 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) -3.6 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 156.91 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 46.8 ChemAxon
Polarizability 20.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Trehalose Degradation SMP00467 Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023183
KNApSAcK ID Not Available
Chemspider ID 388538 Link_out
KEGG Compound ID C01172 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03498 Link_out
Metagene Link HMDB03498 Link_out
METLIN ID Not Available
PubChem Compound 439427 Link_out
PDB ID BG6 Link_out
ChEBI ID 17719 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Glucokinase
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-1
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HK1
Uniprot ID: P19367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate 1-dehydrogenase
Reactions:
Beta-D-Glucose 6-phosphate + NADP unknown 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Ion details
Gene Name: G6PD
Uniprot ID: P11413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GDH/6PGL endoplasmic bifunctional protein
Reactions:
Beta-D-Glucose 6-phosphate + NADP unknown 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen Ion details
Gene Name: H6PD
Uniprot ID: O95479 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: ADP-dependent glucokinase
Reactions:
Beta-D-Glucose + ADP unknown Beta-D-Glucose 6-phosphate + Adenosine monophosphate details
Gene Name: ADPGK
Uniprot ID: Q9BRR6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphate isomerase
Reactions:
Glucose 6-phosphate unknown Beta-D-Glucose 6-phosphate details
Beta-D-Glucose 6-phosphate unknown Beta-D-Fructose 6-phosphate details
Gene Name: GPI
Uniprot ID: P06744 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative hexokinase HKDC1
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HKDC1
Uniprot ID: Q2TB90 Link_out
Protein Sequence: FASTA