MiMeDB: Showing metabocard for Fructose 6-phosphate (MMDBc0029473)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:23:42 UTC

Update Date

2024-10-13 08:32:13 UTC

Metabolite ID

MMDBc0029473

Metabolite Identification

Common Name

Fructose 6-phosphate

Description

Fructose-6-phosphate is an important intermediate in glycolysis and gluconeogenesis. The interconversion of glucose-6-phosphate and fructose-6-phosphate, the second step of the Embden-Meyerhof glycolytic pathway, is catalyzed by the enzyme phosphoglucose isomerase (PGI). In gluconeogenesis, fructose-6-phosphate is the immediate precursor of glucose-6-phosphate (wikipedia)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
D-Fructose 6-phosphate	ChEBI
D-Fructose 6-phosphoric acid	ChEBI
Fructose-6-phosphate	ChEBI
Neuberg ester	ChEBI
Fructose-6-phosphoric acid	Generator
Fructose 6-phosphoric acid	Generator
D-Fructose 6-phosphorate	HMDB
D-Fructose-6-p	HMDB
D-Fructose-6-phosphate	HMDB
FPC	HMDB
Fru-6-p	HMDB
Fructose-6-p	HMDB
Fructose-6P	HMDB
Fructose-6-phosphate, (alpha-D)-isomer	HMDB
Fructose-6-phosphate, (beta-D)-isomer	HMDB
Fructose-6-phosphate, disodium salt, (D)-isomer	HMDB
Fructose-6-phosphate, (D)-isomer	HMDB
Fructose-6-phosphate, 1-(14)C-labeled, (D)-isomer	HMDB
Fructose-6-phosphate, 2-(14)C-labeled, (D)-isomer	HMDB
Fructose-6-phosphate, barium (1:1) salt, (D)-isomer	HMDB
Fructose-6-phosphate, barium salt, (D)-isomer	HMDB
Fructose-6-phosphate, sodium salt, (D)-isomer	HMDB
Fructose-6-phosphate, calcium salt, (D)-isomer	HMDB
Fructose-6-phosphate, magnesium (1:1) salt, (D)-isomer	HMDB
Fructose-6-phosphate, sodium salt	HMDB

Molecular Formula

C₆H₁₃O₉P

Average Mass

260.1358

Monoisotopic Mass

260.029718526

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

643-13-0

SMILES

Not Available

InChI Identifier

InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1

InChI Key

GSXOAOHZAIYLCY-HSUXUTPPSA-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
Monosaccharide phosphate
Monoalkyl phosphate
Acyloin
Beta-hydroxy ketone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-fructose 6-phosphate (CHEBI:15946 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cellular Cytoplasm
Feces
Intestine
Prostate
Saliva

Tissue Locations

Intestine
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191881	Glucosamine-6-phosphate isomerase 1	Unknown	P46926	Homo sapiens
MMDBp0191884	Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2	Enzyme	O94808	Homo sapiens
MMDBp0191886	Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1	Enzyme	Q06210	Homo sapiens
MMDBp0192369	6-phosphofructokinase type C	Unknown	Q01813	Homo sapiens
MMDBp0192381	6-phosphofructokinase, liver type	Unknown	P17858	Homo sapiens
MMDBp0192384	6-phosphofructokinase, muscle type	Unknown	P08237	Homo sapiens
MMDBp0192416	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3	Enzyme	Q16875	Homo sapiens
MMDBp0192417	Mannose-6-phosphate isomerase	Unknown	P34949	Homo sapiens
MMDBp0192418	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4	Enzyme	Q16877	Homo sapiens
MMDBp0192419	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1	Enzyme	P16118	Homo sapiens
MMDBp0192421	Fructose-1,6-bisphosphatase isozyme 2	Enzyme	O00757	Homo sapiens
MMDBp0192422	Transaldolase	Enzyme	P37837	Homo sapiens
MMDBp0192423	Fructose-1,6-bisphosphatase 1	Unknown	P09467	Homo sapiens
MMDBp0192424	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2	Enzyme	O60825	Homo sapiens
MMDBp0192425	Transketolase	Unknown	P29401	Homo sapiens
MMDBp0192426	Glucose-6-phosphate isomerase	Enzyme	P06744	Homo sapiens
MMDBp0196018	Glucosamine-6-phosphate isomerase 2	Enzyme	Q8TDQ7	Homo sapiens
MMDBp0196993	Fructose-2,6-bisphosphatase TIGAR	Unknown	Q9NQ88

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001208	D-Fructose 2,6-bisphosphate	Fructose 6-phosphate	fructose-1,6-bisphosphatase 1	VMH; KEGG	30371894
MMDBr0001918	Fructose 6-phosphate	D-Fructose 2,6-bisphosphate	Not Available	VMH; KEGG	30371894
MMDBr0002481	Fructose 6-phosphate	Fructose 1,6-bisphosphate	Not Available	VMH	11945275 4276999
MMDBr0002517	D-Fructose	Fructose 6-phosphate	hexokinase 1	VMH	16906315 7061426 7150652 8717435
MMDBr0002518	Deoxyadenosine triphosphate	Fructose 6-phosphate	hexokinase 1	VMH	16906315 7061426 7150652 8717435
MMDBr0007058	Fructose 6-phosphate	Acetyl phosphate	Not Available	VMH	30371894
MMDBr0007399	Fructose 1,6-bisphosphate	Fructose 6-phosphate	Not Available	VMH	30371894
MMDBr0007420	beta-D-Glucose 6-phosphate	Fructose 6-phosphate	Not Available	VMH	30371894
MMDBr0007424	Fructose 6-phosphate	Glucosamine 6-phosphate	Not Available	VMH	30371894
MMDBr0007484	Mannose 6-phosphate	Fructose 6-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0007521	Glucose 6-phosphate	Fructose 6-phosphate	Not Available	VMH	30371894
MMDBr0007574	Glyceraldehyde 3-phosphate	D-Erythrose 4-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0007579	D-Erythrose 4-phosphate	Fructose 6-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0007819	Glucosamine 6-phosphate	Fructose 6-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0007864	D-Fructose	Fructose 6-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0007936	Fructose 6-phosphate	Fructose 1,6-bisphosphate	Not Available	VMH	30371894
MMDBr0007962	D-Sorbitol 6-phosphate	Fructose 6-phosphate	Not Available	VMH	30371894
MMDBr0010598	beta-D-Glucose 6-phosphate	Fructose 6-phosphate	glucose-6-phosphate isomerase	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	Slight Increase	Association	Human Saliva	HMDB	23857558
Frontotemporal dementia	Increased	Association	Human Saliva	HMDB	23857558

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	247	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human subgingival plaque; Chicken	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	425	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	140	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human subgingival plaque; Human supragingival plaque; Human urine	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	4	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	21	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	16	Human feces; Human saliva	Unknown
Eukaryota/Fungi	Basidiomycota	1
Archaea/Archaea	Crenarchaeota	4		Metabolic reconstruction
Bacteria	Aquificae	1
Archaea/Archaea	Euryarchaeota	13		Metabolic reconstruction
Eukaryota/Fungi	Microsporidia	1
Bacteria	Chlamydiae	5	Human ; Sheep
Bacteria	Chlorobi	1
Bacteria	Cyanobacteria	2
Bacteria	nah	2
Bacteria	Thermotogae	1
Bacteria	Deinococcus-thermus	2
Viruses/Bamfordvirae	Nucleocytoviricota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Plant	Root	Daucus carota ssp. sativus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Saliva	Detected and Quantified	1.01	0.47			uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Saliva	Detected and Quantified	1.46	0.81			uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Saliva	Detected and Quantified	1.57	1.71			uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Cellular cytoplasm	Detected and Quantified	49.6				uM	Adult (>18 years old)	Both	Normal	HMDB	15925468
Human Saliva	Detected and Quantified	1.73	0.81			uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Cellular cytoplasm	Detected and Quantified	16.0		13.0	19.0	uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Blood	Detected and Quantified	10.2	1.8			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	9.9	2.3			uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.173	0.176			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.208	0.352			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.210	0.164			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.368	0.249			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.370	0.197			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.403	0.286			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.413	0.225			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.551	0.364			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000124

DrugBank ID

DB04493

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021896

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15946

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Roberts NB, Dutton J, Helliwell T, Rothwell PJ, Kavanagh JP: Pyrophosphate in synovial fluid and urine and its relationship to urinary risk factors for stone disease. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):529-34. doi: 10.1177/000456329202900507. [PubMed:1332571 ]
Gapparov MM, Virovets OA: [Nonenzymatic glycosylation of serum albumin and thymic DNA by food monosugars and their natural metabolites that form in the body]. Vopr Pitan. 1990 Jan-Feb;(1):36-40. [PubMed:2346009 ]
Karlander S, Roovete A, Vranic M, Efendic S: Glucose and fructose 6-phosphate cycle in humans. Am J Physiol. 1986 Nov;251(5 Pt 1):E530-6. doi: 10.1152/ajpendo.1986.251.5.E530. [PubMed:3777162 ]
Alton G, Hasilik M, Niehues R, Panneerselvam K, Etchison JR, Fana F, Freeze HH: Direct utilization of mannose for mammalian glycoprotein biosynthesis. Glycobiology. 1998 Mar;8(3):285-95. doi: 10.1093/glycob/8.3.285. [PubMed:9451038 ]
Gagnon M, Kheadr EE, Le Blay G, Fliss I: In vitro inhibition of Escherichia coli O157:H7 by bifidobacterial strains of human origin. Int J Food Microbiol. 2004 Apr 1;92(1):69-78. doi: 10.1016/j.ijfoodmicro.2003.07.010. [PubMed:15033269 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Markuszewski MJ, Szczykowska M, Siluk D, Kaliszan R: Human red blood cells targeted metabolome analysis of glycolysis cycle metabolites by capillary electrophoresis using an indirect photometric detection method. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):636-42. doi: 10.1016/j.jpba.2005.04.015. [PubMed:15925468 ]
Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. doi: 10.1016/j.jchromb.2005.01.001. Epub 2005 Jan 23. [PubMed:16055050 ]
Sanchez B, Champomier-Verges MC, Anglade P, Baraige F, de Los Reyes-Gavilan CG, Margolles A, Zagorec M: Proteomic analysis of global changes in protein expression during bile salt exposure of Bifidobacterium longum NCIMB 8809. J Bacteriol. 2005 Aug;187(16):5799-808. doi: 10.1128/JB.187.16.5799-5808.2005. [PubMed:16077128 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Showing metabocard for Fructose 6-phosphate (MMDBc0029473)

MOL for #<Metabolite:0x0000562ee49b6c20>

3D MOL for #<Metabolite:0x0000562ee49b6c20>

3D SDF for #<Metabolite:0x0000562ee49b6c20>

3D-SDF for #<Metabolite:0x0000562ee49b6c20>

PDB for #<Metabolite:0x0000562ee49b6c20>

3D PDB for #<Metabolite:0x0000562ee49b6c20>

SMILES for #<Metabolite:0x0000562ee49b6c20>

INCHI for #<Metabolite:0x0000562ee49b6c20>

Structure for #<Metabolite:0x0000562ee49b6c20>

3D Structure for #<Metabolite:0x0000562ee49b6c20>