AFCDB: Glucosamine (FDB022668)

Record Information

Version

1.0

Creation date

2011-09-21 00:17:41 UTC

Update date

2019-11-26 03:21:05 UTC

Primary ID

FDB022668

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glucosamine

Description

Glucosamine belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Glucosamine is a very strong basic compound (based on its pKa). Glucosamine has been detected, but not quantified in, several different foods, such as milk (cow), carrots, green bell peppers, common beans, and yellow bell peppers. This could make glucosamine a potential biomarker for the consumption of these foods.

CAS Number

3416-24-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	551 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3	ChemAxon
logS	0.49	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	116.17 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.58 m³·mol⁻¹	ChemAxon
Polarizability	16.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H13NO5

IUPAC name

(3S,4S,5R,6S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol

InChI Identifier

InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m0/s1

InChI Key

MSWZFWKMSRAUBD-HOWGCPQDSA-N

Isomeric SMILES

[H][C@@]1(N)C(O)O[C@@]([H])(CO)[C@]([H])(O)[C@@]1([H])O

Average Molecular Weight

179.1711

Monoisotopic Molecular Weight

179.079372531

Classification

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Amino saccharide
Oxane
1,2-aminoalcohol
Hemiacetal
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Primary amine
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Alcohol
Amine
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-4900000000-364d52fc6e7e423f52bb	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-762e016c89a40a9e3f49	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-bd04d561d78f2abad229	2012-07-24	View Spectrum

NMR

Type	Description		View
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

47977

Phenol-Explorer ID

Not Available

DrugBank ID

DB01296

HMDB ID

HMDB01514

CRC / DFC (Dictionary of Food Compounds) ID

GZV30-O:GZV56-A

EAFUS ID

Not Available

Dr. Duke ID

D-GLUCOSAMINE|GLUCOSAMINE

BIGG ID

34633

KNApSAcK ID

Not Available

HET ID

1QGI

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Glucosamine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti flu	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Glucokinase	GCK	P35557
Hexokinase-3	HK3	P52790
Hexokinase-2	HK2	P52789
Hexokinase-1	HK1	P19367
Tumor necrosis factor	TNF	P01375
Di-N-acetylchitobiase	CTBS	Q01459
Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidase	NGLY1	Q96IV0

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Glucosamine (FDB022668)

Structure for FDB022668 (Glucosamine)