Livestock Metabolome Database: Showing metabocard for D-Mannose (LMDB00076)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:41:50 UTC

Update Date

2021-04-30 20:57:57 UTC

Lmdb

LMDB00076

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Mannose

Description

D-Mannose is a carbohydrate. High-mannose-type oligosaccharides have been shown to play important roles in protein quality control. Several intracellular proteins, such as lectins, chaperones and glycan-processing enzymes, are involved in this process. These include calnexin/calreticulin, UDP-glucose:glycoprotein glucosyltransferase (UGGT), cargo receptors (such as VIP36 and ERGIC-53), mannosidase-like proteins (e.g. EDEM and Htm1p) and ubiquitin ligase (Fbs). They are thought to recognize high-mannose-type glycans with subtly different structures. Mannose-binding lectin (MBL) is an important constituent of the innate immune system. This protein binds through multiple lectin domains to the repeating sugar arrays that decorate many microbial surfaces, and is then able to activate the complement system through a specific protease called MBL-associated protease-2. The primary pathway for the formation of L-fucose in procaryotic and eucaryotic cells is from D-mannose via an internal oxidation reduction and then epimerization of GDP-D-mannose to produce GDP-L-fucose. (PMID: 9488699 , 16154739 , 11414367 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Carubinose	ChEBI
Mannopyranose	ChEBI
Seminose	ChEBI
Mannose	Kegg
D-Mannopyranose	Kegg
(+)-Mannose	HMDB
(+-)-Mannose	HMDB
D(+)-Mannose	HMDB
DL-Mannose	HMDB
Mannopyranoside	HMDB
D Mannose	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

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

Traditional Name

β-glucose

CAS Registry Number

3458-28-4

SMILES

OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1

InChI Key

WQZGKKKJIJFFOK-QTVWNMPRSA-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
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-aldohexose (CHEBI:4208 )
D-mannose (CHEBI:4208 )
mannopyranose (CHEBI:4208 )
Aldoses (C00159 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.92 m³·mol⁻¹	ChemAxon
Polarizability	16.14 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	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-00kb-1931000000-ec423f92582012821c6a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)	splash10-0fr2-1920000000-b6be17dc79a948dfe5fa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)	splash10-00di-9831000000-409527d22fb759cb628f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)	splash10-00di-9621000000-34b421fd962840bfbaec	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)	splash10-066r-1942000000-1c8164b54d2d16c782c3	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)	splash10-0ldi-1942000000-c68a088eba727f3a4ada	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kb-1931000000-ec423f92582012821c6a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-1920000000-b6be17dc79a948dfe5fa	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9831000000-409527d22fb759cb628f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-34b421fd962840bfbaec	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-066r-1942000000-1c8164b54d2d16c782c3	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ldi-1942000000-c68a088eba727f3a4ada	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01pc-6900000000-0ef33e32ee16b7803f1b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-9000000000-27e169c1df0c3ee59806	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03ea-0900000000-9fb0e8db39598c7a269b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-b0bc47623e7b2ca31c02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-648e1637af29cf2a3518	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9200000000-9e6f46a1cbf52d6e347a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-a4ec4f0b1e29e360a952	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-ec2bf4918640a0a36398	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum
Meat
Milk
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Ruminal Fluid	Detected and Quantified	91.3 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	123.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	159.1 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	210.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	125 +/- 25 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	125 +/- 25 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	159 +/- 83 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	211 +/- 86 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	91 +/- 49 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	Fozia Saleem, Sou...	details
Serum	Detected and Quantified	34.8695 +/- 17.3976 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	43.0113 +/- 14.8186 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25372282	details
Serum	Detected and Quantified	31.9915 +/- 16.3798 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	41.14 +/- 14.27 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	31.3238 +/- 9.6713 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	33.2469 +/- 16.5305 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	41.2809 +/- 14.219 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	30.3949 +/- 9.9025 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	37.3579 +/- 22.1426 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	42.5047 +/- 20.0558 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.0973 +/- 13.1146 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	30.2041 +/- 11.9767 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	31.127 +/- 5.388 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.8436 +/- 17.1073 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	30.9705 +/- 10.8713 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.7124 +/- 9.0437 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	29.6137 +/- 10.5605 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	41.6387 +/- 16.1112 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	31.2748 +/- 13.7466 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	36.7447 +/- 9.6924 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.0201 +/- 7.3389 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000169

FooDB ID

FDB001202

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001126

BiGG ID

34085

BioCyc ID

MANNOSE

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Park SH, Pastuszak I, Drake R, Elbein AD: Purification to apparent homogeneity and properties of pig kidney L-fucose kinase. J Biol Chem. 1998 Mar 6;273(10):5685-91. [9488699 ]
Ito Y, Hagihara S, Matsuo I, Totani K: Structural approaches to the study of oligosaccharides in glycoprotein quality control. Curr Opin Struct Biol. 2005 Oct;15(5):481-9. [16154739 ]
Jack DL, Klein NJ, Turner MW: Mannose-binding lectin: targeting the microbial world for complement attack and opsonophagocytosis. Immunol Rev. 2001 Apr;180:86-99. [11414367 ]

Showing metabocard for D-Mannose (LMDB00076)

Structure for LMDB00076 (D-Mannose)