Bovine Metabolome Database: Showing metabocard for Fructose 1,6-bisphosphate (BMDB0001058)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:40:30 UTC

Update Date

2020-05-19 22:01:06 UTC

BMDB ID

BMDB0001058

Secondary Accession Numbers

BMDB01058

Metabolite Identification

Common Name

Fructose 1,6-bisphosphate

Description

Fructose 1,6-bisphosphate, also known as fosfructose or SR-FDP, 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. Fructose 1,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Fructose 1,6-bisphosphate exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,6-Di-O-phosphono-beta-D-fructofuranose	ChEBI
BETA FRUCTOSE 1,6-diphosphATE	ChEBI
beta-D-Fructose 1,6-bisphosphate	ChEBI
Fosfructose	ChEBI
1,6-Di-O-phosphono-b-D-fructofuranose	Generator
1,6-Di-O-phosphono-β-D-fructofuranose	Generator
b FRUCTOSE 1,6-diphosphate	Generator
b FRUCTOSE 1,6-diphosphoric acid	Generator
beta FRUCTOSE 1,6-diphosphoric acid	Generator
Β fructose 1,6-diphosphate	Generator
Β fructose 1,6-diphosphoric acid	Generator
b-D-Fructose 1,6-bisphosphate	Generator
b-D-Fructose 1,6-bisphosphoric acid	Generator
beta-D-Fructose 1,6-bisphosphoric acid	Generator
Β-D-fructose 1,6-bisphosphate	Generator
Β-D-fructose 1,6-bisphosphoric acid	Generator
Fructose 1,6-bisphosphoric acid	Generator
Fructose-1,6-diphosphate	HMDB
Fructose-1,6-diphosphate, calcium salt	HMDB
Fructose-1,6-diphosphate, disodium salt	HMDB
Fructose-1,6-diphosphate, trisodium salt	HMDB
Fructose-1,6-diphosphate, 2-(18)O-labeled	HMDB
Fructose-1,6-diphosphate, calcium (1:2) salt	HMDB
Fructose-1,6-diphosphate, monosodium salt	HMDB
Strontium fructose 1,6-diphosphate	HMDB
SR-FDP	HMDB
Fructose 1,6-diphosphate	HMDB
Fructose-1,6-diphosphate, (L)-isomer	HMDB
Fructose-1,6-diphosphate, (alpha-D)-isomer	HMDB
Fructose-1,6-diphosphate, barium (1:2) salt	HMDB
Fructose-1,6-diphosphate, sodium salt, monohydrate	HMDB
Fructose-1,6-diphosphate, tetrasodium salt	HMDB
Strontium fructose-1,6-diphosphate	HMDB
Fructose-1,6-diphosphate magnesium salt	HMDB
Fructose-1,6-diphosphate, (beta-D)-isomer	HMDB
Fructose-1,6-diphosphate, tetrapotassium salt	HMDB
D-Fructose 1,6-biphosphate	HMDB
D-Fructose 1,6-bisphosphate	HMDB
D-Fructose 1,6-diphosphate	HMDB
Diphosphofructose	HMDB
Fructose 1,6-bis(dihydrogen phosphate)	HMDB
beta-D-Fructofuranose 1,6-bisphosphate	HMDB
beta-D-Fructofuranose 1,6-diphosphate	HMDB
beta-D-Fructose 1,6-diphosphate	HMDB
Β-D-fructofuranose 1,6-bisphosphate	HMDB
Β-D-fructofuranose 1,6-diphosphate	HMDB
Β-D-fructose 1,6-diphosphate	HMDB
Fructose 1,6-bisphosphate	MeSH
b-D-Fructofuranose 1,6-bisphosphate	Generator
b-D-Fructofuranose 1,6-bisphosphoric acid	Generator
beta-D-Fructofuranose 1,6-bisphosphoric acid	Generator
Β-D-fructofuranose 1,6-bisphosphoric acid	Generator

Chemical Formula

C₆H₁₄O₁₂P₂

Average Molecular Weight

340.1157

Monoisotopic Molecular Weight

339.996048936

IUPAC Name

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

Traditional Name

[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

RNBGYGVWRKECFJ-ARQDHWQXSA-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

Hexose phosphate
Pentose phosphate
Pentose-5-phosphate
C-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Monoalkyl phosphate
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Tetrahydrofuran
1,2-diol
Hemiacetal
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose 1,6-bisphosphate (CHEBI:28013 )

Ontology

Status

Detected 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)	0.89	ChemAxon
pKa (Strongest Basic)	-3.7	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	25.7 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-MS (7 TMS)	splash10-014i-0497100000-d0c0dfadfe65ee3cc4e5	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)	splash10-014r-1779100000-ba60994aacef73cf8691	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)	splash10-014r-0779100000-b52ccd042ce4169961ed	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01xt-9532000000-c3c4929a4987e34c0dc0	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-03fs-9412510000-0a0a9e96cc6bea61e3c7	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 - n/a 23V, negative	splash10-0006-0190000000-95a4b5217606c0b9d1fb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0002-0900000000-74a1700e0fae0f6aa64e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-000i-0009000000-631b4fa683b46f4c89cb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-000i-1009000000-9df66c58adba653741e0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-000j-7129000000-f1414a0a896a7c132d2d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-0002-9111000000-0fc51e8f6b123f0a5982	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-0002-9100000000-762070874ad885772dc4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 21V, negative	splash10-0002-9100000000-d705002b3a24c5b5ac0f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, negative	splash10-002b-9000000000-caf9814ab914b2093561	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 29V, negative	splash10-004j-9000000000-3b04f1a6a67ed239b001	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, negative	splash10-004i-9000000000-388ef99a8af7f88e6447	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, negative	splash10-004i-9000000000-bc85bd9d38f2c4bf3c58	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0006-0190000000-ba22a78fbbfc1a90ace3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0a4i-0900000000-b559d4679fc0eaa79be7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0002-9530000000-8e5076b641ebc42fb2ef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0fdk-9870000000-6332e12e884d56a6c22b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-6469000000-934f8ed1edcbd28bc667	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006y-7295000000-a5ca0806e65ba8c99e88	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9700000000-02fcc2f4b95b801c5949	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-8509000000-2992f67772e061c3ffe5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-9ac5383c77bff5f6cb96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9d902dae0eabfe2165da	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Liver
Milk
Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	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: 26686724	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001058

DrugBank ID

DB04551

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022397

KNApSAcK ID

Not Available

Chemspider ID

9848

KEGG Compound ID

C05378

BioCyc ID

FRUCTOSE-16-DIPHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Fructose 1,6-bisphosphate

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Yan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10. [PubMed:26686724 ]

Enzymes

Enzyme Details

1. Fructose-1,6-bisphosphatase isozyme 2

General function:: Carbohydrate transport and metabolism
Specific function:: Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations and probably participates in glycogen synthesis from carbohydrate precursors, such as lactate.
Gene Name:: FBP2
Uniprot ID:: Q2KJJ9
Molecular weight:: 36767.0

Enzyme Details

2. Fructose-1,6-bisphosphatase 1

General function:: Carbohydrate transport and metabolism
Specific function:: Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations, acting as a rate-limiting enzyme in gluconeogenesis. Plays a role in regulating glucose sensing and insulin secretion of pancreatic beta-cells. Appears to modulate glycerol gluconeogenesis in liver. Important regulator of appetite and adiposity; increased expression of the protein in liver after nutrient excess increases circulating satiety hormones and reduces appetite-stimulating neuropeptides and thus seems to provide a feedback mechanism to limit weight gain.
Gene Name:: FBP1
Uniprot ID:: Q3SZB7
Molecular weight:: 36728.0

Reactions

Fructose 1,6-bisphosphate + Water → Fructose 6-phosphate + Hydrogen phosphate	details

Enzyme Details

3. ATP-dependent 6-phosphofructokinase, liver type

General function:: Carbohydrate transport and metabolism
Specific function:: Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis (By similarity). Negatively regulates the phagocyte oxidative burst in response to bacterial infection by controlling cellular NADPH biosynthesis and NADPH oxidase-derived reactive oxygen species. Upon macrophage activation, drives the metabolic switch toward glycolysis, thus preventing glucose turnover that produces NADPH via pentose phosphate pathway (By similarity).
Gene Name:: PFKL
Uniprot ID:: A1A4J1
Molecular weight:: 85292.0

Reactions

Fructose 6-phosphate + Adenosine triphosphate → Fructose 1,6-bisphosphate + ADP	details

Enzyme Details

4. ATP-dependent 6-phosphofructokinase, muscle type

General function:: Carbohydrate transport and metabolism
Specific function:: Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis.
Gene Name:: PFKM
Uniprot ID:: Q0IIG5
Molecular weight:: 85294.0

Enzyme Details

5. Fructose-bisphosphate aldolase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOA
Uniprot ID:: A6QLL8
Molecular weight:: 39436.0

Enzyme Details

6. Fructose-bisphosphate aldolase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOC
Uniprot ID:: Q3ZBY4
Molecular weight:: 39382.0

Enzyme Details

7. Fructose-bisphosphate aldolase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOB
Uniprot ID:: A5PK73
Molecular weight:: 39527.0

Enzyme Details

8. Fructose-bisphosphate aldolase B

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ALDOB
Uniprot ID:: Q3T0S5
Molecular weight:: 39543.0

Showing metabocard for Fructose 1,6-bisphosphate (BMDB0001058)

Structure for BMDB0001058 (Fructose 1,6-bisphosphate)

Enzymes

Reactions

Reactions