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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 22:34:16 UTC
Update Date2020-02-26 21:24:39 UTC
HMDB IDHMDB0003514
Secondary Accession Numbers
  • HMDB03514
Metabolite Identification
Common Namealpha-D-Glucose 1,6-bisphosphate
DescriptionGlucose 1,6-diphosphate (G-1,6-P2) is considered to be a major regulator of carbohydrate metabolism. It has been demonstrated that G-1,6-P2 is a potent activator (deinhibitor) of skeletal muscle phosphofructokinase (PFK) and phosphoglucomutase, while being an inhibitor of hexokinase (see Ref. 2). In addition, G-1,6-P2 has been shown to inhibit 6-phosphogluconate dehydrogenase in various rat tissues and fructose 1,6-bisphosphatase in bovine liver. Various factors and conditions affect the tissue content of G-1,6-P2. Specifically, anoxia induces a rapid fall in the content of G-l,6-P2 in the brain. Glucose 1,6-diphosphate has been recognized as a regulatory signal implicated in the control of metabolism, oxygen affinity of red cells, and other cellular functions. The levels of G 1,6-P2 are reduced in the liver and in the muscle of rats with experimentally induced diabetes. In muscle of genetically dystrophic mice, a decrease in the levels of G 1,6-P2 has been found, probably resulting from enhancement of glucose 1,6-P2 phosphatase activity. G 1,6-P2 is an inhibitor of hexokinase and its level is increased significantly after 5 min of exercise (~25%) and then decreased continuously. G 1,6-P2 is a potent allosteric activator of phosphofructokinase, and is markedly decreased in muscles of patients with glycogenosis type VII (muscle phosphofructokinase deficiency) and type V (muscle phosphorylase deficiency). Chronic alcohol intake produces an increase in the concentration of G 1,6-P2 in human muscle before the first sign of myopathy appears. When myopathy is present the level decreases to be similar to healthy humans. These changes could contribute to the decline in skeletal muscle performance (PMID: 1449560 , 2018547 , 2003594 , 3407759 ).
Structure
Data?1582752279
Synonyms
ValueSource
alpha-D-Glucose 1,6-biphosphateChEBI
D-Glucose 1,6-biphosphateChEBI
D-Glucose 1,6-bisphosphateKegg
a-D-Glucose 1,6-biphosphateGenerator
a-D-Glucose 1,6-biphosphoric acidGenerator
alpha-D-Glucose 1,6-biphosphoric acidGenerator
Α-D-glucose 1,6-biphosphateGenerator
Α-D-glucose 1,6-biphosphoric acidGenerator
D-Glucose 1,6-biphosphoric acidGenerator
D-Glucose 1,6-bisphosphoric acidGenerator
a-D-Glucose 1,6-bisphosphateGenerator
a-D-Glucose 1,6-bisphosphoric acidGenerator
alpha-D-Glucose 1,6-bisphosphoric acidGenerator
Α-D-glucose 1,6-bisphosphateGenerator
Α-D-glucose 1,6-bisphosphoric acidGenerator
a-D-Glucose 1,6-bis(dihydrogen phosphate)HMDB
a-D-Glucose 1,6-diphosphateHMDB
alpha-D-1,6-Bis(dihydrogen phosphate) glucopyranoseHMDB
alpha-D-Glucose 1,6-bis(dihydrogen phosphate)HMDB
alpha-D-Glucose 1,6-diphosphateHMDB
alpha-delta-1,6-Bis(dihydrogen phosphate) glucopyranoseHMDB
alpha-delta-Glucose 1,6-bis(dihydrogen phosphate)HMDB
alpha-delta-Glucose 1,6-bisphosphateHMDB
alpha-delta-Glucose 1,6-diphosphateHMDB
D-Glucose 1,6-diphosphateHMDB
delta-Glucose 1,6-diphosphateHMDB
Glucose 1,6-bisphosphateHMDB
Glucose 1,6-diphosphateHMDB
beta-D-Glucose 1,6-(bis)phosphateHMDB
Glucose-1,6-diphosphateHMDB
Glucose-1,6-bisphosphateHMDB
alpha-D-Glucose 1,6-bisphosphateHMDB
alpha-Glucose 1,6-diphosphateHMDB
α-D-Glucose 1,6-diphosphateHMDB
α-Glucose 1,6-diphosphateHMDB
Chemical FormulaC6H14O12P2
Average Molecular Weight340.1157
Monoisotopic Molecular Weight339.996048936
IUPAC Name{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}phosphonic acid
Traditional Name[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxyphosphonic acid
CAS Registry Number10139-18-1
SMILES
O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]1O
InChI Identifier
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
InChI KeyRWHOZGRAXYWRNX-VFUOTHLCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-4.374Not Available
Predicted Properties
PropertyValueSource
Water Solubility16 g/LALOGPS
logP-1.6ALOGPS
logP-3.2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.67 m³·mol⁻¹ChemAxon
Polarizability24.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9422000000-7bfff1b0b2d51cca5dffSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fr5-7922130000-d6ba2057c5f43a10b976Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002f-9182000000-23bca820b90a45f17acbSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-00dl-0089000000-14b2732dbc26e1c46650Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-03di-0090000000-eff1032954c312ffe781Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-03di-0019000000-b6e1680b5b949ae7c8f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-03xr-0069000000-63772b51257cee2af15aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-014i-0092000000-65fab63b500e60a0ea01Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-014i-0190000000-bfbcf573cf5f756927f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-01b9-0790000000-757dcf8e67df0907f65aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-00di-0920000000-18f7c04ce401fda68354Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-014i-0090000000-e9698a8c472de2ec65b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-00fr-0930000000-7f0cb15d50e589a9640fSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-0002-0910000000-4a92067b100f48729122Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-0002-0390000000-c8d4b6af4a7e1dbc6766Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-004i-0069000000-b2d82f85ee47b9928a9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 23V, positivesplash10-004i-0091000000-e9e211cdeab0d7aab3abSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-014i-0000900000-386775c642a8d4f6b7b3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-014i-0004900000-249416017fe86caa0eb1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-014i-0109200000-91fd1405fb3d3ce23e3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-014i-0309000000-71838f11ad810bfe78acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2169000000-7496db21481f5c6646f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-8194000000-0ab11c338e7462b1784eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9710000000-04febc887536086e1a99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-7319000000-8f0f5f6bb5550e944766Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e67858a197b35311ba75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-44fd1ff1d686ff20aa4fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified98.0 +/- 17.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02835
Phenol Explorer Compound IDNot Available
FooDB IDFDB023185
KNApSAcK IDNot Available
Chemspider ID74362
KEGG Compound IDC01231
BioCyc IDALPHA-GLUCOSE-16-BISPHOSPHATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound82400
PDB IDNot Available
ChEBI ID18148
Food Biomarker OntologyNot Available
VMH IDM01966
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the synthesis of the GDP-mannose and dolichol-phosphate-mannose required for a number of critical mannosyl transfer reactions (By similarity).
Gene Name:
PMM2
Uniprot ID:
O15305
Molecular weight:
28081.925
General function:
Involved in cytochrome-c oxidase activity
Specific function:
This is the heme A-containing chain of cytochrome c oxidase, the terminal oxidase in mitochondrial electron transport
Gene Name:
COX5A
Uniprot ID:
P20674
Molecular weight:
16762.0
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of the nucleoside breakdown products ribose-1-phosphate and deoxyribose-1-phosphate to the corresponding 5-phosphopentoses. May also catalyze the interconversion of glucose-1-phosphate and glucose-6-phosphate. Has low glucose 1,6-bisphosphate synthase activity.
Gene Name:
PGM2
Uniprot ID:
Q96G03
Molecular weight:
68282.765
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Glucose 1,6-bisphosphate synthase using 1,3-bisphosphoglycerate as a phosphate donor and a series of 1-phosphate sugars as acceptors, including glucose 1-phosphate, mannose 1-phosphate, ribose 1-phosphate and deoxyribose 1-phosphate. 5 or 6-phosphosugars are bad substrates, with the exception of glucose 6-phosphate. Also synthesizes ribose 1,5-bisphosphate. Has only low phosphopentomutase and phosphoglucomutase activities.
Gene Name:
PGM2L1
Uniprot ID:
Q6PCE3
Molecular weight:
70441.085
Reactions
Glyceric acid 1,3-biphosphate + Glucose 1-phosphate → 3-Phosphoglyceric acid + alpha-D-Glucose 1,6-bisphosphatedetails