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Record Information
Version1.0
Creation Date2016-09-30 22:20:28 UTC
Update Date2020-05-21 16:28:41 UTC
BMDB IDBMDB0000169
Secondary Accession Numbers
  • BMDB00169
Metabolite Identification
Common NameD-Mannose
DescriptionD-Mannose, also known as mannopyranose or carubinose, 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. D-Mannose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Mannose exists in all living species, ranging from bacteria to humans. D-Mannose can be converted into mannose 6-phosphate; which is mediated by the enzyme hexokinase-1. In cattle, D-mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway.
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
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Lysosome
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point132 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility713.0 mg/mL at 17 °CNot 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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00kb-1931000000-ec423f92582012821c6aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0fr2-1920000000-b6be17dc79a948dfe5faView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)splash10-00di-9831000000-409527d22fb759cb628fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)splash10-00di-9621000000-34b421fd962840bfbaecView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-066r-1942000000-1c8164b54d2d16c782c3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0ldi-1942000000-c68a088eba727f3a4adaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-1931000000-ec423f92582012821c6aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-1920000000-b6be17dc79a948dfe5faView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9831000000-409527d22fb759cb628fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-34b421fd962840bfbaecView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066r-1942000000-1c8164b54d2d16c782c3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ldi-1942000000-c68a088eba727f3a4adaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01pc-6900000000-0ef33e32ee16b7803f1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9000000000-27e169c1df0c3ee59806View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ea-0900000000-9fb0e8db39598c7a269bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a3518View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a36398View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Lysosome
  • Myelin sheath
Biospecimen Locations
  • Adrenal Medulla
  • Bladder
  • Blood
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Milk
  • Muscle
  • Neuron
  • Pancreas
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal MedullaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
EpidermisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
    • Kurt J. Boudonck,...
details
MuscleDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
NeuronExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified91 +/- 49 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified159 +/- 83 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified211 +/- 86 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified125 +/- 25 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified125 +/- 25 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified91.3 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified159.1 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified210.9 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified123.6 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified763.813 +/- 751.731 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified91.62 +/- 25.1 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SpleenExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Mycobacterium avium subsp. paratuberculosis infection
details
Ruminal FluidDetected and Quantified210.97 +/- 83.15 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified2415.813 +/- 1248.434 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000169
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001202
KNApSAcK IDC00001126
Chemspider ID17893
KEGG Compound IDC00159
BioCyc IDMANNOSE
BiGG ID34085
Wikipedia LinkMannose
METLIN IDNot Available
PubChem Compound18950
PDB IDNot Available
ChEBI ID4208
References
Synthesis ReferenceSowden, John C.; Fischer, Hermann O. L. Condensation of nitromethane with D- and L-arabinose: preparation of L-glucose and L-mannose. Journal of the American Chemical Society (1947), 69 1963-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.

Enzymes

General function:
Involved in serine-type endopeptidase activity
Specific function:
Converts the abundant, but inactive, zymogen plasminogen to plasmin by hydrolyzing a single Arg-Val bond in plasminogen. By controlling plasmin-mediated proteolysis, it plays an important role in tissue remodeling and degradation, in cell migration and many other physiopathological events.
Gene Name:
PLAT
Uniprot ID:
Q28198
Molecular weight:
63701.0
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:
HK1
Uniprot ID:
P27595
Molecular weight:
103064.0
Reactions
D-Mannose + Adenosine triphosphate → Mannose 6-phosphate + ADPdetails
General function:
Carbohydrate transport and metabolism
Specific function:
Lectin that binds to various sugars: mannose = ManNAc > fucose > GlcNAc > glucose = maltose > galactose > lactose > GalNAc. Could play a role in immune defense.
Gene Name:
CL43
Uniprot ID:
P42916
Molecular weight:
33616.0
General function:
Involved in glycoprotein binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q95M44
Molecular weight:
5436.0
General function:
Involved in mannose binding
Specific function:
Plays an important role in targeting the monocarboxylate transporters SLC16A1, SLC16A3, SLC16A8, SLC16A11 and SLC16A12 to the plasma membrane. Plays pivotal roles in spermatogenesis, embryo implantation, neural network formation and tumor progression. Stimulates adjacent fibroblasts to produce matrix metalloproteinases (MMPS). Seems to be a receptor for oligomannosidic glycans. In vitro, promotes outgrowth of astrocytic processes.
Gene Name:
BSG
Uniprot ID:
Q865R3
Molecular weight:
22119.0
General function:
Involved in mannose binding
Specific function:
Transport of phosphorylated lysosomal enzymes from the Golgi complex and the cell surface to lysosomes. Lysosomal enzymes bearing phosphomannosyl residues bind specifically to mannose-6-phosphate receptors in the Golgi apparatus and the resulting receptor-ligand complex is transported to an acidic prelyosomal compartment where the low pH mediates the dissociation of the complex.
Gene Name:
M6PR
Uniprot ID:
P11456
Molecular weight:
31201.0
General function:
Involved in binding
Specific function:
Lectin that plays a role in innate immunity, apoptosis and embryogenesis. Calcium-dependent lectin that binds self and non-self glycoproteins presenting high mannose oligosaccharides with at least one terminal alpha-1,2-linked mannose epitope. Primarily recognizes the terminal disaccharide of the glycan. Also recognizes a subset of fucosylated glycans and lipopolysaccharides. Plays a role in innate immunity through its ability to bind non-self sugars presented by microorganisms and to activate the complement through the recruitment of MAPS1. Also plays a role in apoptosis through its ability to bind in a calcium-independent manner the DNA present at the surface of apoptotic cells and to activate the complement in response to this binding. Finally, plays a role in development, probably serving as a guidance cue during the migration of neural crest cells and other cell types during embryogenesis.
Gene Name:
COLEC11
Uniprot ID:
Q17QH6
Molecular weight:
28333.0
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
CL46
Uniprot ID:
Q8MHZ9
Molecular weight:
37445.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
lman1
Uniprot ID:
Q8MJ82
Molecular weight:
5976.0
General function:
Involved in calcium ion binding
Specific function:
Not Available
Gene Name:
MBL-A
Uniprot ID:
Q5I2B0
Molecular weight:
26308.0
General function:
Not Available
Specific function:
Substrate-recognition component of some SCF (SKP1-CUL1-F-box protein)-type E3 ubiquitin ligase complexes. Involved in endoplasmic reticulum-associated degradation pathway (ERAD) for misfolded lumenal proteins by recognizing and binding sugar chains on unfolded glycoproteins that are retrotranslocated into the cytosol and promoting their ubiquitination and subsequent degradation. Able to recognize and bind denatured glycoproteins, which are modified with not only high-mannose but also complex-type oligosaccharides. Also recognizes sulfated glycans. Also involved in DNA damage response by specifically recognizing activated CHEK1 (phosphorylated on 'Ser-345'), promoting its ubiquitination and degradation. Ubiquitination of CHEK1 is required to insure that activated CHEK1 does not accumulate as cells progress through S phase, or when replication forks encounter transient impediments during normal DNA replication (By similarity).
Gene Name:
FBXO6
Uniprot ID:
Q3SX24
Molecular weight:
30767.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q7M2U1
Molecular weight:
1267.0
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
PLIN3
Uniprot ID:
Q3SX32
Molecular weight:
47603.0
General function:
Involved in glycoprotein binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q862E4
Molecular weight:
15486.0
General function:
Carbohydrate transport and metabolism
Specific function:
Calcium-dependent lectin-like protein which binds to a yeast cell wall extract and immune complexes through the complement component (C3bi). It is capable of binding non-reducing terminal N-acetylglucosamine, mannose, and fucose residues.
Gene Name:
CGN1
Uniprot ID:
P23805
Molecular weight:
37995.0
General function:
Cell cycle control, cell division, chromosome partitioning
Specific function:
Acrosin is the major protease of mammalian spermatozoa. It is a serine protease of trypsin-like cleavage specificity, it is synthesized in a zymogen form, proacrosin and stored in the acrosome.
Gene Name:
bovine proacrosine
Uniprot ID:
P79343
Molecular weight:
41722.0
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent lectin involved in innate immune defense. Binds mannose, fucose and N-acetylglucosamine on different microorganisms and activates the lectin complement pathway. Binds to late apoptotic cells, as well as to apoptotic blebs and to necrotic cells, but not to early apoptotic cells, facilitating their uptake by macrophages (By similarity).
Gene Name:
MBL
Uniprot ID:
O02659
Molecular weight:
26471.0
General function:
Involved in receptor activity
Specific function:
Acts as a positive regulator of T-cell coactivation, by binding DPP4 (By similarity). Transport of phosphorylated lysosomal enzymes from the Golgi complex and the cell surface to lysosomes. Lysosomal enzymes bearing phosphomannosyl residues bind specifically to mannose-6-phosphate receptors in the Golgi apparatus and the resulting receptor-ligand complex is transported to an acidic prelyosomal compartment where the low pH mediates the dissociation of the complex. This receptor also binds IGF2.
Gene Name:
IGF2R
Uniprot ID:
P08169
Molecular weight:
274529.0
General function:
Not Available
Specific function:
Removes terminal alpha-N-acetylgalactosamine residues from glycolipids and glycopeptides. Required for the breakdown of glycolipids (By similarity).
Gene Name:
NAGA
Uniprot ID:
Q58DH9
Molecular weight:
46533.0
Reactions
D-Galactose + D-Mannose → Epimelibiosedetails