Cannabis Compound Database: Showing Compound Card for Fructose 1,6-bisphosphate (CDB004879)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9) Show 14 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:46:15 UTC

Updated at

2020-11-18 16:38:55 UTC

CannabisDB ID

CDB004879

Secondary Accession Numbers

Not Available

Cannabis Compound 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. Within humans, fructose 1,6-bisphosphate participates in a number of enzymatic reactions. In particular, fructose 1,6-bisphosphate can be converted into fructose 6-phosphate through the action of the enzyme fructose-1,6-bisphosphatase 1. In addition, fructose 1,6-bisphosphate can be converted into dihydroxyacetone phosphate and D-glyceraldehyde 3-phosphate; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. In humans, fructose 1,6-bisphosphate is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. Outside of the human body, Fructose 1,6-bisphosphate has been detected, but not quantified in, several different foods, such as rices, peach (var.), other soy products, celery leaves, and white lupines. This could make fructose 1,6-bisphosphate a potential biomarker for the consumption of these foods. A D-fructofuranose 1,6-bisphosphate with a beta-configuration at the anomeric position. Fructose 1,6-bisphosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

340.12

Monoisotopic Molecular Weight

339.996

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

34693-15-7

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Blood

Subcellular:

Cytoplasm

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	94 mg/mL	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	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Fructose 1,6-bisphosphate, 7 TMS, GC-MS Spectrum	splash10-014i-0497100000-d0c0dfadfe65ee3cc4e5	Spectrum
GC-MS	Fructose 1,6-bisphosphate, 1 MEOX; 7 TMS, GC-MS Spectrum	splash10-014r-1779100000-ba60994aacef73cf8691	Spectrum
GC-MS	Fructose 1,6-bisphosphate, 1 MEOX; 7 TMS, GC-MS Spectrum	splash10-014r-0779100000-b52ccd042ce4169961ed	Spectrum
Predicted GC-MS	Fructose 1,6-bisphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01xt-9532000000-c3c4929a4987e34c0dc0	Spectrum
Predicted GC-MS	Fructose 1,6-bisphosphate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03fs-9412510000-0a0a9e96cc6bea61e3c7	Spectrum
Predicted GC-MS	Fructose 1,6-bisphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0006-0190000000-95a4b5217606c0b9d1fb	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0002-0900000000-74a1700e0fae0f6aa64e	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-000i-0009000000-631b4fa683b46f4c89cb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-000i-1009000000-9df66c58adba653741e0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-000j-7129000000-f1414a0a896a7c132d2d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-0002-9111000000-0fc51e8f6b123f0a5982	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-0002-9100000000-762070874ad885772dc4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 21V, negative	splash10-0002-9100000000-d705002b3a24c5b5ac0f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, negative	splash10-002b-9000000000-caf9814ab914b2093561	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 29V, negative	splash10-004j-9000000000-3b04f1a6a67ed239b001	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, negative	splash10-004i-9000000000-388ef99a8af7f88e6447	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, negative	splash10-004i-9000000000-bc85bd9d38f2c4bf3c58	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0006-0190000000-ba22a78fbbfc1a90ace3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0a4i-0900000000-b559d4679fc0eaa79be7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0002-9530000000-8e5076b641ebc42fb2ef	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-0fdk-9870000000-6332e12e884d56a6c22b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 23V, negative	splash10-004i-9000000000-5ef060d5ec4b80c35c1a	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0007-6469000000-934f8ed1edcbd28bc667	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006y-7295000000-a5ca0806e65ba8c99e88	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9700000000-02fcc2f4b95b801c5949	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-8509000000-2992f67772e061c3ffe5	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-9ac5383c77bff5f6cb96	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9d902dae0eabfe2165da	2015-09-15	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycolysis
Gluconeogenesis
Fructose and Mannose Degradation
Pentose Phosphate Pathway
Fructosuria		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
6-phosphofructokinase type C	PFKP	10p15.3-p15.2	Q01813	details
6-phosphofructokinase, liver type	PFKL	21q22.3	P17858	details
6-phosphofructokinase, muscle type	PFKM	12q13.3	P08237	details
Fructose-1,6-bisphosphatase isozyme 2	FBP2	9q22.3	O00757	details
Fructose-1,6-bisphosphatase 1	FBP1	9q22.3	P09467	details
Fructose-bisphosphate aldolase A	ALDOA	16p11.2	P04075	details
Fructose-bisphosphate aldolase C	ALDOC	17cen-q12	P09972	details
Fructose-bisphosphate aldolase B	ALDOB	9q21.3-q22.2	P05062	details
Fructose-bisphosphate aldolase			Q8NHT3	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
6-phosphofructokinase type C	PFKP	10p15.3-p15.2	Q01813	details
6-phosphofructokinase, liver type	PFKL	21q22.3	P17858	details
6-phosphofructokinase, muscle type	PFKM	12q13.3	P08237	details
Fructose-1,6-bisphosphatase isozyme 2	FBP2	9q22.3	O00757	details
Fructose-1,6-bisphosphatase 1	FBP1	9q22.3	P09467	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001058

DrugBank ID

DB04551

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Only showing the first 10 proteins. There are 14 proteins in total.

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Enzymes

Enzyme Details

1. 6-phosphofructokinase type C

General function:: Involved in 6-phosphofructokinase activity
Specific function:: Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:: PFKP
Uniprot ID:: Q01813
Molecular weight:: 85595.405

Enzyme Details

2. 6-phosphofructokinase, liver type

General function:: Involved in 6-phosphofructokinase activity
Specific function:: Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:: PFKL
Uniprot ID:: P17858
Molecular weight:: 85017.825

Enzyme Details

3. 6-phosphofructokinase, muscle type

General function:: Involved in 6-phosphofructokinase activity
Specific function:: Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:: PFKM
Uniprot ID:: P08237
Molecular weight:: 85181.925

Enzyme Details

4. Fructose-1,6-bisphosphatase isozyme 2

General function:: Involved in phosphoric ester hydrolase activity
Specific function:: Not Available
Gene Name:: FBP2
Uniprot ID:: O00757
Molecular weight:: 36742.84

Enzyme Details

5. Fructose-1,6-bisphosphatase 1

General function:: Involved in phosphoric ester hydrolase activity
Specific function:: Not Available
Gene Name:: FBP1
Uniprot ID:: P09467
Molecular weight:: 36842.145

Enzyme Details

6. Fructose-bisphosphate aldolase A

General function:: Involved in fructose-bisphosphate aldolase activity
Specific function:: Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
Gene Name:: ALDOA
Uniprot ID:: P04075
Molecular weight:: 39419.675

Enzyme Details

7. Fructose-bisphosphate aldolase C

General function:: Involved in fructose-bisphosphate aldolase activity
Specific function:: Not Available
Gene Name:: ALDOC
Uniprot ID:: P09972
Molecular weight:: 39455.505

Enzyme Details

8. Fructose-bisphosphate aldolase B

General function:: Involved in fructose-bisphosphate aldolase activity
Specific function:: Not Available
Gene Name:: ALDOB
Uniprot ID:: P05062
Molecular weight:: 39472.715

Enzyme Details

9. Fructose-bisphosphate aldolase

General function:: Involved in fructose-bisphosphate aldolase activity
Specific function:: D-fructose 1,6-bisphosphate = glycerone phosphate + D-glyceraldehyde 3-phosphate
Gene Name:: Not Available
Uniprot ID:: Q8NHT3
Molecular weight:: 34750.6

Only showing the first 10 proteins. There are 14 proteins in total.

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Showing Compound Card for Fructose 1,6-bisphosphate (CDB004879)

Structure for CDB004879 (Fructose 1,6-bisphosphate)

Enzymes