Bovine Metabolome Database: Showing metabocard for Glucosamine 6-phosphate (BMDB0001254)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:43:08 UTC

Update Date

2020-05-21 16:28:28 UTC

BMDB ID

BMDB0001254

Secondary Accession Numbers

BMDB01254

Metabolite Identification

Common Name

Glucosamine 6-phosphate

Description

Glucosamine 6-phosphate, also known as GLCN-6-p or glucose-6-phosphoric acid, 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. Glucosamine 6-phosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Glucosamine 6-phosphate exists in all living species, ranging from bacteria to humans. Glucosamine 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Glucosamine 6-phosphate and acetic acid can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme putative N-acetylglucosamine-6-phosphate deacetylase. In addition, Glucosamine 6-phosphate can be converted into N-acetyl-D-glucosamine 6-phosphate; which is catalyzed by the enzyme glucosamine 6-phosphate N-acetyltransferase. In cattle, glucosamine 6-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.

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

Chemical Formula

C₆H₁₄NO₈P

Average Molecular Weight

259.151

Monoisotopic Molecular Weight

259.045702941

IUPAC Name

{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid

Traditional Name

α-D-glucosamine 6-phosphate

CAS Registry Number

3616-42-0

SMILES

N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O

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 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Lysosome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-4.2	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	21.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052b-9320000000-54466a568e39d51598c7	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0ik9-3912400000-c198d10e982d681785ed	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0970000000-095ba413dfd29c80b445	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9500000000-e4e82ba86236d6046d0d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-bd232a0933f76298e943	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03di-0190000000-778d1a36aaf5c9b3c846	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-08i0-1690000000-f08f9e49e698f1aa134d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9010000000-8a6a96ec67621a842ce8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002b-9010000000-8a6a96ec67621a842ce8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0190000000-280711606909adbb8814	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-08i0-1690000000-f08f9e49e698f1aa134d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-3190000000-0f9d6942fba86f12422e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03fr-2790000000-7fe42a3d5900a5984d04	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0490000000-818ec0fe39e531f561a4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-9850000000-40bb2cfef099c426fcbf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kmj-9500000000-9bb59bf1855e5fa76305	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0699-8950000000-68f380f4fab22160c728	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-4f7a2c18e5b29f9e6076	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-6fc65d9a14f58d847a4f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0790000000-d9873144345380710376	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9810000000-32a2cffa4a376910fdb3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-9000000000-7be390edddedcba28a23	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-054k-9040000000-fd7b28df2dbc578cfc0b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9010000000-f0f082b70bb688bd4b38	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Lysosome

Biospecimen Locations

Epidermis
Milk
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glutamate Metabolism		Not Available
Amino Sugar Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29291809	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

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

References

Synthesis Reference

Cacioppo, F.; Pandolfo, L.; Arena, E. Synthesis of glucosamine 6-phosphate in tissues of rachitic rats. Giorn. Biochim. (1964), 13(4), 249-55.

Material Safety Data Sheet (MSDS)

Not Available

General References

Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details

1. Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins (By similarity).
Gene Name:: GFPT2
Uniprot ID:: Q08DQ2
Molecular weight:: 77081.0

Reactions

Fructose 6-phosphate + L-Glutamine → Glucosamine 6-phosphate + L-Glutamic acid	details

Enzyme Details

2. Hexokinase-1

General function:: Involved in ATP binding
Specific function:: Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:: HK1
Uniprot ID:: P27595
Molecular weight:: 103064.0

Reactions

Glucosamine + Adenosine triphosphate → Glucosamine 6-phosphate + ADP	details

Enzyme Details

3. Glucosamine-6-phosphate isomerase 2

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: GNPDA2
Uniprot ID:: Q17QL1
Molecular weight:: 31165.0

Enzyme Details

4. N-acetylglucosamine-6-phosphate deacetylase

General function:: Carbohydrate transport and metabolism
Specific function:: Hydrolyzes the N-glycolyl group from N-glycolylglucosamine 6-phosphate (GlcNGc-6-P) in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway.
Gene Name:: AMDHD2
Uniprot ID:: A7MBC0
Molecular weight:: 43496.0

Reactions

N-Acetyl-D-Glucosamine 6-Phosphate + Water → Glucosamine 6-phosphate + Acetic acid	details

Enzyme Details

5. Glucosamine-6-phosphate isomerase 1

General function:: Not Available
Specific function:: Seems to trigger calcium oscillations in mammalian eggs. These oscillations serve as the essential trigger for egg activation and early development of the embryo (By similarity).
Gene Name:: GNPDA1
Uniprot ID:: A4FV08
Molecular weight:: 32580.0

Reactions

Glucosamine 6-phosphate + Water → Fructose 6-phosphate + Ammonia	details

Enzyme Details

6. Glucosamine 6-phosphate N-acetyltransferase

General function:: Not Available
Specific function:: Not Available
Gene Name:: GNPNAT1
Uniprot ID:: Q08DV2
Molecular weight:: 20776.0

Reactions

Acetyl-CoA + Glucosamine 6-phosphate → N-Acetyl-D-Glucosamine 6-Phosphate + Coenzyme A	details

Showing metabocard for Glucosamine 6-phosphate (BMDB0001254)

Structure for BMDB0001254 (Glucosamine 6-phosphate)

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions