P. aeruginosa Metabolome Database: alpha-D-Glucose 1,6-bisphosphate (PAMDB000508)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000508

Identification

Name:

alpha-D-Glucose 1,6-bisphosphate

Description:

Alpha-D-glucose 1,6-bisphosphate is considered to be a major regulator of carbohydrate metabolism. Glucose 1,6-diphosphate (G 1,6-P2) have been recognized as a regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. G 1,6-P2 is a potent allosteric activator of phosphofructokinase.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

α-D-glucopyranose, 1,6-bis(dihydrogen phosphate)
α-D-glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
α-D-glucose-1,6-P2
α-D-glucose-1,6-P₂
a-D-1,6-Bis(dihydrogen phosphate) glucopyranose
a-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
a-D-Glucopyranose, 1,6-bis(dihydrogen phosphate)
a-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
A-D-Glucose 1,6-bis(dihydrogen phosphate)
a-D-Glucose 1,6-bis(dihydrogen phosphoric acid)
A-D-Glucose 1,6-bisphosphate
a-D-Glucose 1,6-bisphosphoric acid
A-D-Glucose 1,6-diphosphate
a-D-Glucose 1,6-diphosphoric acid
a-D-Glucose-1,6-P2
a-delta-1,6-Bis(dihydrogen phosphate) glucopyranose
a-delta-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
a-delta-Glucose 1,6-bis(dihydrogen phosphate)
a-delta-Glucose 1,6-bis(dihydrogen phosphoric acid)
a-delta-Glucose 1,6-bisphosphate
a-delta-Glucose 1,6-bisphosphoric acid
a-delta-Glucose 1,6-diphosphate
a-delta-Glucose 1,6-diphosphoric acid
a-δ-1,6-Bis(dihydrogen phosphate) glucopyranose
a-δ-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
a-δ-Glucose 1,6-bis(dihydrogen phosphate)
a-δ-Glucose 1,6-bis(dihydrogen phosphoric acid)
a-δ-Glucose 1,6-bisphosphate
a-δ-Glucose 1,6-bisphosphoric acid
a-δ-Glucose 1,6-diphosphate
a-δ-Glucose 1,6-diphosphoric acid
Alpha-D-1,6-Bis(dihydrogen phosphate) Glucopyranose
alpha-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
Alpha-D-Glucopyranose, 1,6-bis(dihydrogen phosphate)
alpha-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
Alpha-D-Glucose 1,6-bis(dihydrogen phosphate)
alpha-D-Glucose 1,6-bis(dihydrogen phosphoric acid)
Alpha-D-Glucose 1,6-bisphosphate
alpha-D-Glucose 1,6-bisphosphoric acid
Alpha-D-Glucose 1,6-diphosphate
alpha-D-Glucose 1,6-diphosphoric acid
Alpha-D-Glucose-1,6-P2
Alpha-delta-1,6-Bis(dihydrogen phosphate) Glucopyranose
alpha-delta-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
Alpha-delta-Glucose 1,6-bis(dihydrogen phosphate)
alpha-delta-Glucose 1,6-bis(dihydrogen phosphoric acid)
Alpha-delta-Glucose 1,6-bisphosphate
alpha-delta-Glucose 1,6-bisphosphoric acid
Alpha-delta-Glucose 1,6-diphosphate
alpha-delta-Glucose 1,6-diphosphoric acid
D-Glucose 1,6-biphosphate
D-Glucose 1,6-biphosphoric acid
D-Glucose 1,6-bisphosphate
D-Glucose 1,6-bisphosphoric acid
D-Glucose 1,6-diphosphate
D-Glucose 1,6-diphosphoric acid
Delta-Glucose 1,6-diphosphate
delta-Glucose 1,6-diphosphoric acid
Glucose 1,6-bisphosphate
Glucose 1,6-bisphosphoric acid
Glucose 1,6-diphosphate
Glucose 1,6-diphosphoric acid
Glucose-1,6-bisphosphate
Glucose-1,6-bisphosphoric acid
Glucose-1,6-diphosphate
Glucose-1,6-diphosphoric acid
α-D-1,6-Bis(dihydrogen phosphate) glucopyranose
α-D-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
α-D-Glucopyranose, 1,6-bis(dihydrogen phosphate)
α-D-Glucopyranose, 1,6-bis(dihydrogen phosphoric acid)
α-D-Glucose 1,6-bis(dihydrogen phosphate)
α-D-Glucose 1,6-bis(dihydrogen phosphoric acid)
α-D-Glucose 1,6-bisphosphate
α-D-Glucose 1,6-bisphosphoric acid
α-D-Glucose 1,6-diphosphate
α-D-Glucose 1,6-diphosphoric acid
α-D-Glucose-1,6-P2
α-δ-1,6-Bis(dihydrogen phosphate) glucopyranose
α-δ-1,6-Bis(dihydrogen phosphoric acid) glucopyranose
α-δ-Glucose 1,6-bis(dihydrogen phosphate)
α-δ-Glucose 1,6-bis(dihydrogen phosphoric acid)
α-δ-Glucose 1,6-bisphosphate
α-δ-Glucose 1,6-bisphosphoric acid
α-δ-Glucose 1,6-diphosphate
α-δ-Glucose 1,6-diphosphoric acid
δ-Glucose 1,6-diphosphate
δ-Glucose 1,6-diphosphoric acid

Chemical Formula:

C₆H₁₄O₁₂P₂

Average Molecular Weight:

340.1157

Monoisotopic Molecular Weight:

339.996048936

InChI Key:

RWHOZGRAXYWRNX-VFUOTHLCSA-N

InChI:

InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1

CAS number:

10139-18-1

IUPAC Name:

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

Traditional IUPAC Name:

glucose 1,6-bisphosphate

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound 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

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Monosaccharides

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Organic phosphate
Secondary alcohol
Polyol
1,2-diol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucose 1,6-bisphosphate (CHEBI:18148 )

Physical Properties

State:

Solid

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
LogP:	-4.374	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	16.0 mg/mL	ALOGPS
logP	-1.6	ALOGPS
logP	-3.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.89	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.67 m³·mol^-1	ChemAxon
Polarizability	24.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	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:

Pathways:

Starch and sucrose metabolism pae00500

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2169000000-7496db21481f5c6646f1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-8194000000-0ab11c338e7462b1784e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9710000000-04febc887536086e1a99	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-7319000000-8f0f5f6bb5550e944766	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-e67858a197b35311ba75	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-44fd1ff1d686ff20aa4f	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available

References

References:

Cadefau JA, Andres V, Carreras J, Vernet M, Grau JM, Urbano-Marquez A, Cusso R: Glucose 1,6-bisphosphate and fructose 2,6-bisphosphate in muscle from healthy humans and chronic alcoholic patients. Alcohol Alcohol. 1992 May;27(3):253-6. Pubmed: 1449560
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
Katz A, Sahlin K, Broberg S: Regulation of glucose utilization in human skeletal muscle during moderate dynamic exercise. Am J Physiol. 1991 Mar;260(3 Pt 1):E411-5. Pubmed: 2003594
Katz A: G-1,6-P2, glycolysis, and energy metabolism during circulatory occlusion in human skeletal muscle. Am J Physiol. 1988 Aug;255(2 Pt 1):C140-4. Pubmed: 3407759
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Yamada Y, Kono N, Nakajima H, Shimizu T, Kiyokawa H, Kawachi M, Ono A, Nishimura T, Kuwajima M, Tarui S: Low glucose-1, 6-bisphosphate and high fructose-2, 6-bisphosphate concentrations in muscles of patients with glycogenosis types VII and V. Biochem Biophys Res Commun. 1991 Apr 15;176(1):7-10. Pubmed: 2018547

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18148
HMDB ID	HMDB03514
Pubchem Compound ID	82400
Kegg ID	C01231
ChemSpider ID	74362
Wikipedia ID	Not Available
BioCyc ID	ALPHA-GLUCOSE-16-BISPHOSPHATE
EcoCyc ID	ALPHA-GLUCOSE-16-BISPHOSPHATE
Ligand Expo	G16

alpha-D-Glucose 1,6-bisphosphate (PAMDB000508)

Structure for alpha-D-Glucose 1,6-bisphosphate (PAMDB000508)