MiMeDB: Showing metabocard for Glucosamine 6-phosphate (MMDBc0029600)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:33:55 UTC

Update Date

2024-10-13 13:03:44 UTC

Metabolite ID

MMDBc0029600

Metabolite Identification

Common Name

Glucosamine 6-phosphate

Description

Glucosamine 6-phosphate is normally produced via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines. A member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. (PMID 11270676 , 11842094 )

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose	ChEBI
alpha-D-Glucosamine 6-(dihydrogen phosphate)	ChEBI
2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranose	Generator
2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranose	Generator
Glucosamine 6-phosphoric acid	Generator
a-D-Glucosamine 6-(dihydrogen phosphate)	Generator
a-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
α-D-Glucosamine 6-(dihydrogen phosphate)	Generator
α-D-Glucosamine 6-(dihydrogen phosphoric acid)	Generator
2-Amino-2-deoxy-D-glucose 6-phosphate	HMDB
2-Amino-2-deoxyglucose 6-phosphate	HMDB
2-Amino-D-glucose-6-phosphate	HMDB
D-Glucosamine 6-phosphate	HMDB
D-Glucosamine phosphate	HMDB
D-Glucosamine-6-phosphate	HMDB
Glucosamine 6 -phosphate	HMDB
Glucosamine-6-P	HMDB
Glucosamine-6-phosphate	HMDB
Glucose-6-phosphorate	HMDB
Glucose-6-phosphoric acid	HMDB
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester	HMDB
GLCN-6-P	MeSH, HMDB

Molecular Formula

C₆H₁₄NO₈P

Average Mass

259.151

Monoisotopic Mass

259.045702941

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

3616-42-0

SMILES

Not Available

InChI Identifier

InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1

InChI Key

XHMJOUIAFHJHBW-UKFBFLRUSA-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
Amino saccharide
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Hemiacetal
1,2-diol
Secondary alcohol
1,2-aminoalcohol
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic nitrogen compound
Organic oxide
Amine
Primary amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

2-amino-2-deoxy-D-glucopyranose 6-phosphate (CHEBI:15873 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Lysosome

Biospecimen Locations

Feces
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
MMDBp0191726	Glucosamine 6-phosphate N-acetyltransferase	Enzyme	Q96EK6	Homo sapiens
MMDBp0191880	Glucokinase	Enzyme	P35557	Homo sapiens
MMDBp0191881	Glucosamine-6-phosphate isomerase 1	Unknown	P46926	Homo sapiens
MMDBp0191882	Hexokinase-3	Enzyme	P52790	Homo sapiens
MMDBp0191883	Hexokinase-2	Enzyme	P52789	Homo sapiens
MMDBp0191884	Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2	Enzyme	O94808	Homo sapiens
MMDBp0191885	Hexokinase-1	Enzyme	P19367	Homo sapiens
MMDBp0191886	Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1	Enzyme	Q06210	Homo sapiens
MMDBp0193927	Putative N-acetylglucosamine-6-phosphate deacetylase	Enzyme	Q9Y303	Homo sapiens
MMDBp0196018	Glucosamine-6-phosphate isomerase 2	Enzyme	Q8TDQ7	Homo sapiens
MMDBp0196842	Putative hexokinase HKDC1	Unknown	Q2TB90

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000174	Glucosamine 6-phosphate	N-Acetyl-D-Glucosamine 6-Phosphate	Not Available	VMH	30371894
MMDBr0001428	Glucosamine	Glucosamine 6-phosphate	Not Available	VMH; KEGG	30371894
MMDBr0002521	Glucosamine	Glucosamine 6-phosphate	hexokinase 1	VMH; KEGG	30371894
MMDBr0002522	Deoxyadenosine triphosphate	Glucosamine 6-phosphate	hexokinase 1	VMH; KEGG	30371894
MMDBr0007424	Fructose 6-phosphate	Glucosamine 6-phosphate	Not Available	VMH	30371894
MMDBr0007519	D-Glucosamine 1-phosphate	Glucosamine 6-phosphate	Not Available	VMH	30371894
MMDBr0007703	N-Acetyl-D-Glucosamine 6-Phosphate	Acetic acid	Not Available	VMH; KEGG	30371894
MMDBr0007819	Glucosamine 6-phosphate	Fructose 6-phosphate	Not Available	VMH; KEGG	30371894

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	271	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; River trout ; Chicken	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	481	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; Catfish	Metabolic reconstruction
Bacteria	Actinobacteria	141	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	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	127	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	7	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	7	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	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 Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001254

DrugBank ID

DB02657

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022515

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6111

PubChem Compound

439217

PDB ID

Not Available

ChEBI ID

15873

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wu G, Haynes TE, Yan W, Meininger CJ: Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine. Diabetologia. 2001 Feb;44(2):196-202. doi: 10.1007/s001250051599. [PubMed:11270676 ]
Broschat KO, Gorka C, Page JD, Martin-Berger CL, Davies MS, Huang Hc HC, Gulve EA, Salsgiver WJ, Kasten TP: Kinetic characterization of human glutamine-fructose-6-phosphate amidotransferase I: potent feedback inhibition by glucosamine 6-phosphate. J Biol Chem. 2002 Apr 26;277(17):14764-70. doi: 10.1074/jbc.M201056200. Epub 2002 Feb 12. [PubMed:11842094 ]
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 Glucosamine 6-phosphate (MMDBc0029600)

MOL for #<Metabolite:0x00007f46d3f28480>

3D MOL for #<Metabolite:0x00007f46d3f28480>

3D SDF for #<Metabolite:0x00007f46d3f28480>

3D-SDF for #<Metabolite:0x00007f46d3f28480>

PDB for #<Metabolite:0x00007f46d3f28480>

3D PDB for #<Metabolite:0x00007f46d3f28480>

SMILES for #<Metabolite:0x00007f46d3f28480>

INCHI for #<Metabolite:0x00007f46d3f28480>

Structure for #<Metabolite:0x00007f46d3f28480>

3D Structure for #<Metabolite:0x00007f46d3f28480>