Milk Composition Database: Showing metabocard for Glucosamine (BMDB0001514)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:03 UTC

Update Date

2020-05-21 16:26:54 UTC

MCDB ID

BMDB0001514

Secondary Accession Numbers

BMDB01514

Metabolite Identification

Common Name

Glucosamine

Description

Glucosamine, also known as dona or chitosamine, 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glucosamine exists in all living organisms, ranging from bacteria to humans. Glucosamine can be converted into glucosamine 6-phosphate; which is mediated by the enzyme hexokinase-1. In cattle, glucosamine 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-D-glucose	ChEBI
Chitosamine	ChEBI
D-Glucosamine	ChEBI
(+)-2-Amino-2-deoxy-D-glucopyranose	HMDB
(3R,4R,5S,6R)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol	HMDB
2-Amino-2-deoxy-D-glucopyranose	HMDB
2-Amino-2-deoxyglucose	HMDB
2-Aminoglucose	HMDB
2-Deoxy-2-amino-D-glucose	HMDB
2-Deoxy-2-aminoglucose	HMDB
Cosamin	HMDB
D-(+)-Glucosamine	HMDB
Dona	HMDB
Fides ecopharma brand OF glucosamine sulfate	HMDB
Rottapharm brand OF glucosamine sulfate	HMDB
Xicil	HMDB
2 Amino 2 deoxyglucose	HMDB
Glucosamine sulfate	HMDB
Sulfate, glucosamine	HMDB
Dona S	HMDB
Opfermann brand OF glucosamine sulfate	HMDB
Hespercorbin	HMDB

Chemical Formula

C₆H₁₃NO₅

Average Molecular Weight

179.1711

Monoisotopic Molecular Weight

179.079372531

IUPAC Name

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

Traditional Name

glucosamine

CAS Registry Number

3416-24-8

SMILES

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

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?/m1/s1

InChI Key

MSWZFWKMSRAUBD-IVMDWMLBSA-N

Chemical Taxonomy

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

D-glucosamine (CHEBI:47977 )
Amino sugars (C00329 )

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	-2.7	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	16.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tr-9300000000-7e2a89f48724cdda814c	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0ul9-9847700000-b4779809586433e7ec78	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-4900000000-364d52fc6e7e423f52bb	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-762e016c89a40a9e3f49	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-bd04d561d78f2abad229	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9500000000-9bfc2897a4b66f71c7a1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-f842b779439be8970cd9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-074i-9000000000-622ec0743231c0cbaca6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9700000000-5087af92679b2640ba6c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-b9ba212915cbdaed8628	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-2d1825b518f09745e036	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03la-9100000000-3da7ee17d7512a59e3ef	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9400000000-cca17ef05a47a7be4d43	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01x0-9500000000-5fbd02d318d3ec58f98b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0abc-9000000000-11e86d324c183174364e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001i-0900000000-3ba18bb57823024db64e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9500000000-52f44695a6cfb6459105	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9800000000-264ee54a99e01e0d4e30	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-08f87dc3e44979542ca2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-06r6-9000000000-635fa893be82ffdeca97	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03e9-9600000000-09232c8766303805f765	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-4c88765919efa0ec2d2d	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-6900000000-301590fbe90692448d5e	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052g-9100000000-d6a51790ce1df14a067a	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9400000000-e43a7a5cb44f6c461544	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-9800000000-56b95ef43b164db5524d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-1434c5ce1e9649c1cbf1	2016-08-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View 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)	Not Available	2018-05-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2018-05-25	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 23438684	details
Detected but not Quantified	Not Applicable		PMID: 27999311	details

External Links

HMDB ID

HMDB0001514

DrugBank ID

DB01296

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022668

KNApSAcK ID

Not Available

Chemspider ID

388352

KEGG Compound ID

C00329

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

47977

References

Synthesis Reference

Li, Nan; Li, Jiheng. Preparation of D-glucosamine hydrochloride. Zhongguo Yaoke Daxue Xuebao (1997), 28(1), 56-58.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]

Showing metabocard for Glucosamine (BMDB0001514)

Structure for BMDB0001514 (Glucosamine)