D-Glucosamine 6-phosphate (BioCAD00000009346)

placenta

Metabolite Card

Formula: C6H14NO8P (259.0457)
SMILES: N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O

Synonyms [en]

D-glucosamine 6-phosphate; D-glucosamine phosphate; glucosamine 6-phosphate; 2-amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose; alpha-D-glucosamine 6-(dihydrogen phosphate); 2-amino-2-deoxy-D-glucopyranose 6-(dihydrogen phosphate)

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

D-Glucosamine 6-phosphate. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000009346). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Glucosamine 6-phosphate (CAS: 3616-42-0) is normally produced in endothelial cells via de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals.It is 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. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus (PMID:11270676, 11842094).

Cytoplasm Lysosome
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 3616-42-0
  • CAS Registry Number: 55722-81-1
  • CAS Registry Number: 6815-93-6
  • CAS Registry Number: 70442-23-8
  • PubChem: 3645
  • PubChem: 439217
  • PubChem: 440997
  • ChEBI: ChEBI:12962
  • ChEBI: ChEBI:15873
  • ChEBI: ChEBI:47987
  • HMDB: HMDB0001254
  • KEGG: C00352
  • BioCyc: CPD-13469
  • NCBI MeSH: glucosamine 6-phosphate
  • DrugBank: DB02657
  • RefMet: RM0136090
  • MoNA: BAF_UVA_POS000554
  • MoNA: BAF_UVA_POS001268
  • MoNA: BAF_UVA_POS001269
  • MoNA: BAF_UVA_POS001270
  • MoNA: BAF_UVA_POS001271
  • MoNA: CCMSLIB00000578159
  • MoNA: CCMSLIB00005464341
  • MoNA: CCMSLIB00005464469
  • MoNA: CCMSLIB00005464470
  • MoNA: CCMSLIB00005464471
  • MoNA: CCMSLIB00005720371
  • MoNA: CCMSLIB00005720661
  • MoNA: EMBL-MCF_spec33658
  • MoNA: EMBL_MCF_2_0_HRMS_Library000068
  • MoNA: EMBL_MCF_2_0_HRMS_Library000228
  • MoNA: EMBL_MCF_2_0_HRMS_Library000305
  • MoNA: FiehnHILIC000385
  • MoNA: FiehnHILIC001213
  • MoNA: FiehnHILIC002727
  • MoNA: HMDB0001254_ms_ms_1484
  • MoNA: HMDB0001254_ms_ms_1485
  • MoNA: HMDB0001254_ms_ms_1486
  • MoNA: KO002954
  • MoNA: KO002955
  • MoNA: KO002956
  • MoNA: KO002957
  • MoNA: KO002958
  • MoNA: KO008968
  • MoNA: KO008969
  • MoNA: MoNA001704
  • MoNA: MoNA001705
  • MoNA: MoNA001706
  • MoNA: MoNA011021
  • MoNA: MoNA011022
  • MoNA: MoNA011023
  • MoNA: MoNA011024
  • MoNA: MoNA016711
  • MoNA: MoNA024154
  • MoNA: MoNA024173
  • MoNA: MoNA032640
  • MoNA: MoNA032642
  • MoNA: MoNA032643
  • MoNA: MoNA034769
  • MoNA: MoNA034770
  • MoNA: MoNA034771
  • MoNA: MoNA037386
  • MoNA: MoNA038132
  • MoNA: PR100067
  • MoNA: PR100068
  • MoNA: PR100516
  • MoNA: PS011901
  • MoNA: PS011902
  • MoNA: PS011907
  • Metlin: METLIN_3390
  • Coconut NaturalProduct: CNP0340664.1
  • Coconut NaturalProduct: CNP0340664.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00765 3.5.99.6 D-glucosamine-6-phosphate aminohydrolase (ketol isomerizing);
KEGG:R00768 2.6.1.16 L-glutamine:D-fructose-6-phosphate isomerase (deaminating);
KEGG:R01961 2.7.1.1 ATP:D-glucosamine 6-phosphotransferase
KEGG:R01964 2.7.1.1 ITP:D-glucosamine 6-phosphotransferase
KEGG:R01965 2.7.1.1 dATP:D-glucosamine 6-phosphotransferase
KEGG:R02058 2.3.1.4 acetyl-CoA:D-glucosamine-6-phosphate N-acetyltransferase
KEGG:R02059 3.5.1.25 N-acetyl-D-glucosamine-6-phosphate amidohydrolase
KEGG:R02060 5.4.2.10 D-glucosamine 1-phosphate 1,6-phosphomutase;
KEGG:R02631 2.7.1.- protein-N(pi)-phosphohistidine:D-glucosamine 6-phosphotransferase
KEGG:R12220 5.1.3.42 D-glucosamine 6-phosphate 4-epimerase
KEGG:R12594 2.7.1.147 ADP:D-glucosamine 6-phosphotransferase
BioCyc:GLUCOSAMINE-6-P-DEAMIN-RXN 3.5.99.6 CPD-13469 + WATER<=>FRUCTOSE-6P + AMMONIUM
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Organism Source

Taxonomy Source

  1. Escherichia coli [ncbi taxid: 562]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY-6517 N-acetylglucosamine degradation II
BioCyc:META_GLNSYN-PWY L-glutamine biosynthesis I
BioCyc:META_PWY-6906 chitin derivatives degradation
BioCyc:META_PWY-5505 L-glutamate and L-glutamine biosynthesis
BioCyc:META_P441-PWY superpathway of N-acetylneuraminate degradation
BioCyc:ECO_GLNSYN-PWY L-glutamine biosynthesis I
BioCyc:YEAST_UDPNAGSYN-YEAST-PWY UDP-N-acetylglucosamine biosynthesis
BioCyc:YEAST_PWY-6981 chitin biosynthesis
BioCyc:SHIGELLA_UDPNAGSYN-PWY UDP-N-acetyl-D-glucosamine biosynthesis I
BioCyc:SHIGELLA_GLCMANNANAUT-PWY superpathway of N-acetylglucosamine, N-acetylmannosamine and N-acetylneuraminate degradation
BioCyc:SHIGELLA_PWY-6517 N-acetylglucosamine degradation II
BioCyc:SHIGELLA_PWY0-1261 anhydromuropeptides recycling
BioCyc:MTBH37RV_GLUAMCAT-PWY N-acetylglucosamine degradation I
BioCyc:MTBCDC1551_UDPNAGSYN-PWY UDP-N-acetyl-D-glucosamine biosynthesis I
BioCyc:MTBCDC1551_PWY0-1261 anhydromuropeptides recycling
BioCyc:AGRO_UDPNAGSYN-PWY UDP-N-acetyl-D-glucosamine biosynthesis I
BioCyc:SCO_UDPNAGSYN-PWY UDP-N-acetyl-D-glucosamine biosynthesis I
BioCyc:SYNEL_PWY0-1261 anhydromuropeptides recycling
BioCyc:PDIF272563_GLUAMCAT-PWY N-acetylglucosamine degradation I
BioCyc:BTHE_GLUAMCAT-PWY N-acetylglucosamine degradation I
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