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Record Information
Version1.0
Creation Date2016-07-13 19:41:50 UTC
Update Date2021-04-30 20:57:57 UTC
LmdbLMDB00076
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Mannose
DescriptionD-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
Thumb
Synonyms
ValueSource
CarubinoseChEBI
MannopyranoseChEBI
SeminoseChEBI
MannoseKegg
D-MannopyranoseKegg
(+)-MannoseHMDB
(+-)-MannoseHMDB
D(+)-MannoseHMDB
DL-MannoseHMDB
MannopyranosideHMDB
D MannoseHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameβ-glucose
CAS Registry Number3458-28-4
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 KeyWQZGKKKJIJFFOK-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00kb-1931000000-ec423f92582012821c6aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0fr2-1920000000-b6be17dc79a948dfe5faSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)splash10-00di-9831000000-409527d22fb759cb628fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)splash10-00di-9621000000-34b421fd962840bfbaecSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-066r-1942000000-1c8164b54d2d16c782c3Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0ldi-1942000000-c68a088eba727f3a4adaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-1931000000-ec423f92582012821c6aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-1920000000-b6be17dc79a948dfe5faSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9831000000-409527d22fb759cb628fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-34b421fd962840bfbaecSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066r-1942000000-1c8164b54d2d16c782c3Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ldi-1942000000-c68a088eba727f3a4adaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01pc-6900000000-0ef33e32ee16b7803f1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9000000000-27e169c1df0c3ee59806Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ea-0900000000-9fb0e8db39598c7a269bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a3518Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a952Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a36398Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Meat
  • Milk
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
Ruminal FluidDetected and Quantified91.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified123.6 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified159.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified210.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified125 +/- 25 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified125 +/- 25 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified159 +/- 83 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified211 +/- 86 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified91 +/- 49 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Fozia Saleem, Sou...
details
SerumDetected and Quantified34.8695 +/- 17.3976 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified43.0113 +/- 14.8186 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified31.9915 +/- 16.3798 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified41.14 +/- 14.27 uMNot AvailableOvine
    • Candidate serum m...
details
SerumDetected and Quantified31.3238 +/- 9.6713 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified33.2469 +/- 16.5305 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified41.2809 +/- 14.219 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified30.3949 +/- 9.9025 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified37.3579 +/- 22.1426 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified42.5047 +/- 20.0558 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified34.0973 +/- 13.1146 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified30.2041 +/- 11.9767 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified31.127 +/- 5.388 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified34.8436 +/- 17.1073 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified30.9705 +/- 10.8713 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified35.7124 +/- 9.0437 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified29.6137 +/- 10.5605 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified41.6387 +/- 16.1112 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified31.2748 +/- 13.7466 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified36.7447 +/- 9.6924 uM
Normal
Ovine
    • Goldansaz et al.,...
details
SerumDetected and Quantified34.0201 +/- 7.3389 uM
Normal
Ovine
    • Goldansaz et al.,...
details
DrugBank IDNot Available
HMDB IDHMDB0000169
FooDB IDFDB001202
Phenol Explorer IDNot Available
KNApSAcK IDC00001126
BiGG ID34085
BioCyc IDMANNOSE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMannose
Chemspider ID17893
ChEBI ID4208
PubChem Compound ID18950
Kegg Compound IDC00159
YMDB IDYMDB00894
ECMDB IDECMDB00169
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]