MiMeDB: Showing metabocard for beta-D-Fructose 1,6-bisphosphate (MMDBc0030043)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:51:46 UTC

Update Date

2024-10-11 02:50:28 UTC

Metabolite ID

MMDBc0030043

Metabolite Identification

Common Name

beta-D-Fructose 1,6-bisphosphate

Description

Beta-D-fructose 1,6-bisphosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. The hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate is a key reaction of carbohydrate metabolism. (PMID 3008716 ) Fructose-1,6-bisphosphate (F-1,6-P2) is an allosteric activator of two key enzymes of glycolysis: phosphofructokinase and pyruvate kinase. (PMID 18025560 ) In gluconeogenesis, fructose 6-phosphate is formed from fructose 1,6-bisphosphate, and if fructose 1,6-bisphosphate were reformed by the phosphofructokinase reaction there would be a "gluconeogenic futile cycle". (PMID 6217196 ) Fructose-1,6-bisphosphate (FBP) aldolase is an essential glycolytic enzyme that reversibly cleaves its ketohexose substrate into triose phosphates. (PMID 14699122 ) Fructose 1-phosphate is a metabolite that plays a regulatory role in metabolism and is best measured using an assay based on its conversion to fructose 1,6-bisphosphate by a bacterial fructose-1-phosphate kinase (Fru1PK). (PMID 10833389 ) For growth, the assimilated fructose is sequentially phosphorylated by ATP and (i) manno(fructo)kinase, to form fructose 6-phosphate, and (ii) phosphofructokinase, to form fructose 1,6-bisphosphate, which is a member of central routes of glycolysis and gluconeogenesis. (PMID 17159144 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₆H₁₄O₁₂P₂

Average Mass

340.1157

Monoisotopic Mass

339.996048936

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

125740-83-2

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cellular Cytoplasm
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
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
MMDBp0192421	Fructose-1,6-bisphosphatase isozyme 2	Enzyme	O00757	Homo sapiens
MMDBp0192423	Fructose-1,6-bisphosphatase 1	Unknown	P09467	Homo sapiens
MMDBp0192590	Fructose-bisphosphate aldolase A	Enzyme	P04075	Homo sapiens
MMDBp0192591	Fructose-bisphosphate aldolase C	Enzyme	P09972	Homo sapiens
MMDBp0192592	Fructose-bisphosphate aldolase B	Enzyme	P05062	Homo sapiens
MMDBp0196247	Fructose-bisphosphate aldolase	Enzyme	Q8NHT3	Homo sapiens
MMDBp0196248	Fructose-bisphosphate aldolase	Enzyme	A8MVZ9	Homo sapiens
MMDBp0196249	Fructose-bisphosphate aldolase	Enzyme	A4UCT0	Homo sapiens
MMDBp0196250	Fructose-bisphosphate aldolase	Enzyme	A4UCS9	Homo sapiens
MMDBp0196251	Fructose-bisphosphate aldolase	Enzyme	Q5T7D5	Homo sapiens
MMDBp0196252	Fructose-bisphosphate aldolase	Enzyme	A8K430	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	472	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Cattle ; River trout ; Turkey ; Sheep ; Lion ; Chicken	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	473	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Catfish	Metabolic reconstruction
Bacteria	Actinobacteria	135	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	124	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	11	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	15	Human feces; Human ; Goat ; Pig	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Aquificae	3
Archaea/Archaea	Euryarchaeota	19		Metabolic reconstruction
Bacteria	Thermotogae	4
Bacteria	Cyanobacteria	30	Human
Eukaryota/Fungi	Ascomycota	14	Human feces; Human saliva; Human supragingival plaque
Bacteria	Chlorobi	11
Bacteria	nah	2
Archaea/Archaea	Thaumarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	5		Metabolic reconstruction
Bacteria	Deinococcus-thermus	4
Bacteria	Dictyoglomi	1
Archaea/Archaea	nah	1
Eukaryota/Fungi	Microsporidia	1
nah	1
Bacteria	Chlamydiae	3	Human
Bacteria	Chloroflexi	3
Archaea	nah	2

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cellular cytoplasm	Detected and Quantified	7.60		3.60	11.6	uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Blood	Detected and Quantified	1.2	0.4			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	3.8	0.7			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 Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Norne JE, Lilja H, Lindman B, Einarsson R, Zeppezauer M: Pt(CN)2-4 and Au(CN)-2: potential general probes for anion-binding sites of proteins. 35Cl and 81Br nuclear-magnetic-resonance studies. Eur J Biochem. 1975 Nov 15;59(2):463-73. doi: 10.1111/j.1432-1033.1975.tb02475.x. [PubMed:1204623 ]
Nakai A, Shigematsu Y, Liu YY, Kikawa Y, Sudo M: Urinary sugar phosphates and related organic acids in fructose-1,6-diphosphatase deficiency. J Inherit Metab Dis. 1993;16(2):408-14. doi: 10.1007/BF00710290. [PubMed:8412001 ]
Acan NL, Ozer N: Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate. J Enzyme Inhib. 2001 Nov;16(5):457-64. doi: 10.1080/14756360109162395. [PubMed:11916152 ]
Ahn SM, Yoon HY, Lee BG, Park KC, Chung JH, Moon CH, Lee SH: Fructose-1,6-diphosphate attenuates prostaglandin E2 production and cyclo-oxygenase-2 expression in UVB-irradiated HaCaT keratinocytes. Br J Pharmacol. 2002 Oct;137(4):497-503. doi: 10.1038/sj.bjp.0704896. [PubMed:12359631 ]
Riedel BJ, Gal J, Ellis G, Marangos PJ, Fox AW, Royston D: Myocardial protection using fructose-1,6-diphosphate during coronary artery bypass graft surgery: a randomized, placebo-controlled clinical trial. Anesth Analg. 2004 Jan;98(1):20-29. doi: 10.1213/01.ANE.0000094336.97693.90. [PubMed:14693576 ]
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 ]
Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
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 ]

Showing metabocard for beta-D-Fructose 1,6-bisphosphate (MMDBc0030043)

MOL for #<Metabolite:0x000055b2ed932c40>

3D MOL for #<Metabolite:0x000055b2ed932c40>

3D SDF for #<Metabolite:0x000055b2ed932c40>

3D-SDF for #<Metabolite:0x000055b2ed932c40>

PDB for #<Metabolite:0x000055b2ed932c40>

3D PDB for #<Metabolite:0x000055b2ed932c40>

SMILES for #<Metabolite:0x000055b2ed932c40>

INCHI for #<Metabolite:0x000055b2ed932c40>

Structure for #<Metabolite:0x000055b2ed932c40>

3D Structure for #<Metabolite:0x000055b2ed932c40>