Showing Compound Glucosamine 6-phosphate (FDB022515)

Record Information

Version

1.0

Creation date

2011-09-21 00:15:11 UTC

Update date

2019-11-26 03:21:04 UTC

Primary ID

FDB022515

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glucosamine 6-phosphate

Description

Glucosamine 6-phosphate is normally produced in endothelial cells via the 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. 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) [HMDB]

CAS Number

3616-42-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2-amino-2-Deoxy-6-O-ONO-a-D-glucopyranose	Generator
2-amino-2-Deoxy-6-O-ONO-alpha-D-glucopyranose	ChEBI
2-amino-2-Deoxy-6-O-ONO-α-D-glucopyranose	Generator
2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranose	Generator
2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose	ChEBI
2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranose	Generator
2-amino-2-Deoxy-D-glucose 6-ate	HMDB
2-Amino-2-deoxy-D-glucose 6-phosphate	HMDB
2-amino-2-Deoxyglucose 6-ate	HMDB
2-Amino-2-deoxyglucose 6-phosphate	HMDB

Showing 1 to 10 of 49 entries

Predicted Properties

Property	Value	Source
Water Solubility	34.8 g/L	ALOGPS
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	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H14NO8P

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

259.151

Monoisotopic Molecular Weight

259.045702941

Classification

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

Endogenous

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Glucosamine 6-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052b-9320000000-54466a568e39d51598c7	Spectrum
Predicted GC-MS	Glucosamine 6-phosphate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ik9-3912400000-c198d10e982d681785ed	Spectrum
Predicted GC-MS	Glucosamine 6-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0970000000-095ba413dfd29c80b445	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-053r-9500000000-e4e82ba86236d6046d0d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9000000000-bd232a0933f76298e943	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03di-0190000000-778d1a36aaf5c9b3c846	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-08i0-1690000000-f08f9e49e698f1aa134d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9010000000-8a6a96ec67621a842ce8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002b-9010000000-8a6a96ec67621a842ce8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0190000000-280711606909adbb8814	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-08i0-1690000000-f08f9e49e698f1aa134d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-03di-3190000000-0f9d6942fba86f12422e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03fr-2790000000-7fe42a3d5900a5984d04	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0490000000-818ec0fe39e531f561a4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-9850000000-40bb2cfef099c426fcbf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kmj-9500000000-9bb59bf1855e5fa76305	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0699-8950000000-68f380f4fab22160c728	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-4f7a2c18e5b29f9e6076	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-6fc65d9a14f58d847a4f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0790000000-d9873144345380710376	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9810000000-32a2cffa4a376910fdb3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-9000000000-7be390edddedcba28a23	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-054k-9040000000-fd7b28df2dbc578cfc0b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9010000000-f0f082b70bb688bd4b38	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

388356

ChEMBL ID

Not Available

KEGG Compound ID

C00352

Pubchem Compound ID

439217

Pubchem Substance ID

Not Available

ChEBI ID

15873

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01254

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34709

KNApSAcK ID

Not Available

HET ID

GLP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Glucokinase	GCK	P35557
Glucosamine 6-phosphate N-acetyltransferase	GNPNAT1	Q96EK6
Glucosamine-6-phosphate isomerase 2	GNPDA2	Q8TDQ7
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1	GFPT1	Q06210
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2	GFPT2	O94808
Hexokinase-1	HK1	P19367
Hexokinase-2	HK2	P52789
Hexokinase-3	HK3	P52790
Putative N-acetylglucosamine-6-phosphate deacetylase	AMDHD2	Q9Y303