Bovine Metabolome Database: Showing metabocard for D-Fructose 2,6-bisphosphate (BMDB0001047)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:40:21 UTC

Update Date

2020-05-19 22:01:06 UTC

BMDB ID

BMDB0001047

Secondary Accession Numbers

BMDB01047

Metabolite Identification

Common Name

D-Fructose 2,6-bisphosphate

Description

D-D-d-fructose 2,6-bisphosphate, also known as d-fructose 2,6-bisphosphate, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-D-d-fructose 2,6-bisphosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). D-D-d-fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. D-D-d-fructose 2,6-bisphosphate can be converted into fructose 6-phosphate; which is mediated by the enzyme 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1. In cattle, D-d-fructose 2,6-bisphosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,6-Di-O-phosphono-beta-D-fructofuranose	ChEBI
2,6-Di-O-phosphono-b-D-fructofuranose	Generator
2,6-Di-O-phosphono-β-D-fructofuranose	Generator
D-Fructose 2,6-bisphosphoric acid	Generator
b-D-Fructose 2,6-bisphosphate	HMDB
beta-D-Fructose 2,6-bisphosphate	HMDB
Fru 2,6-P2, fructose 2,6-diphosphate	HMDB
Fructose 2,6-bisphosphate	HMDB
Fructose 2,6-biphosphate	MeSH, HMDB
Fructose 2,6-diphosphate	MeSH, HMDB
Phosphofructokinase activation factor	MeSH, HMDB
Phosphofructokinase activator	MeSH, HMDB
Fructose-2,6-diphosphate	MeSH, HMDB
D-Fructose 2,6-diphosphate	HMDB
beta-D-Fructose 2,6-diphosphate	HMDB
β-D-Fructose 2,6-diphosphate	HMDB

Chemical Formula

C₆H₁₄O₁₂P₂

Average Molecular Weight

340.1157

Monoisotopic Molecular Weight

339.996048936

IUPAC Name

{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

fructose-2,6-diphosphate

CAS Registry Number

79082-92-1

SMILES

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

InChI Identifier

InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1

InChI Key

YXWOAJXNVLXPMU-ZXXMMSQZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
C-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Alkyl phosphate
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose 2,6-bisphosphate (CHEBI:28602 )

Ontology

Status

Expected but not 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	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.5	ALOGPS
logP	-3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.68	ChemAxon
pKa (Strongest Basic)	-3.5	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	6	ChemAxon
Refractivity	58.11 m³·mol⁻¹	ChemAxon
Polarizability	25.24 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01dj-0963000000-090736f476a618727455	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00tb-0972000000-e47c74a14376eaabd8c3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01dj-0963000000-090736f476a618727455	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00tb-0972000000-e47c74a14376eaabd8c3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9512000000-82418e0e398490357c5e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-2190010000-53cf738181713979e181	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, negative	splash10-000i-0019000000-7b58b1d6169f22e732a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, negative	splash10-000m-2496000000-40ad2c4944ae5c0701f3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, negative	splash10-0002-9830000000-a9cbb8a3dba391a8858b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, negative	splash10-002b-9200000000-6dcaff4e5eee3799656f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 50V, negative	splash10-004j-9100000000-9851b59e56acb7c5802c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-3797000000-cb11e27ce8d0be902a39	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9132000000-b908246df46f54e31180	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dm-9600000000-19262e5981934144e1aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-7409000000-0240bd8771cde252759c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-8930f98e412f1b68e30b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fb204edc71835bcbaaad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0393000000-f7f716e45f745f0bec68	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1920000000-f0eccbb835449758a67c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-9410000000-f9f76bd919e86701aaff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9008000000-d519306c146482d051d0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9001000000-2d0e9375a49babbe9d93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-bc05f33d90e2bf18235c	View in MoNA
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fructose and Mannose Degradation		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001047

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Fructose_2,6-bisphosphate

METLIN ID

5964

PubChem Compound

105021

PDB ID

Not Available

ChEBI ID

28602

References

Synthesis Reference

Shulman, Hagit; Makarov, Carina; Ogawa, Anthony K.; Romesberg, Floyd; Keinan, Ehud. Chemically Reactive Immunogens Lead to Functional Convergence of the Immune Response. Journal of the American Chemical Society (2000), 122(44), 10743-10753.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1

General function:: Carbohydrate transport and metabolism
Specific function:: Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:: PFKFB1
Uniprot ID:: P49872
Molecular weight:: 54657.0

Reactions

D-Fructose 2,6-bisphosphate + Water → Fructose 6-phosphate + Hydrogen phosphate	details

Enzyme Details

2. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3

General function:: Carbohydrate transport and metabolism
Specific function:: Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:: PFKFB3
Uniprot ID:: Q28901
Molecular weight:: 53584.0

Enzyme Details

3. 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2

General function:: Carbohydrate transport and metabolism
Specific function:: Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name:: PFKFB2
Uniprot ID:: P26285
Molecular weight:: 60811.0

Enzyme Details

4. Fructose-2,6-bisphosphatase TIGAR

General function:: Carbohydrate transport and metabolism
Specific function:: Fructose-bisphosphatase hydrolyzing fructose-2,6-bisphosphate as well as fructose-1,6-bisphosphate (By similarity). Acts as a negative regulator of glycolysis by lowering intracellular levels of fructose-2,6-bisphosphate in a p53/TP53-dependent manner, resulting in the pentose phosphate pathway (PPP) activation and NADPH production. Contributes to the generation of reduced glutathione to cause a decrease in intracellular reactive oxygen species (ROS) content, correlating with its ability to protect cells from oxidative or metabolic stress-induced cell death. Plays a role in promoting protection against cell death during hypoxia by decreasing mitochondria ROS levels in a HK2-dependent manner through a mechanism that is independent of its fructose-bisphosphatase activity. In response to cardiac damage stress, mediates p53-induced inhibition of myocyte mitophagy through ROS levels reduction and the subsequent inactivation of BNIP3. Reduced mitophagy results in an enhanced apoptotic myocyte cell death, and exacerbates cardiac damage. Plays a role in adult intestinal regeneration; contributes to the growth, proliferation and survival of intestinal crypts following tissue ablation. Plays a neuroprotective role against ischemic brain damage by enhancing PPP flux and preserving mitochondria functions. Protects glioma cells from hypoxia- and ROS-induced cell death by inhibiting glycolysis and activating mitochondrial energy metabolism and oxygen consumption in a TKTL1-dependent and p53/TP53-independent manner. Plays a role in cancer cell survival by promoting DNA repair through activating PPP flux in a CDK5-ATM-dependent signaling pathway during hypoxia and/or genome stress-induced DNA damage responses. Involved in intestinal tumor progression.
Gene Name:: TIGAR
Uniprot ID:: Q1JQA7
Molecular weight:: 29467.0

Showing metabocard for D-Fructose 2,6-bisphosphate (BMDB0001047)

Structure for BMDB0001047 (D-Fructose 2,6-bisphosphate)

Enzymes

Reactions