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Identification
YMDB IDYMDB00894
NameD-Mannose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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 is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Mannose exists in all living species, ranging from bacteria to humans. D-mannose can be converted into mannose 6-phosphate; which is catalyzed by the enzyme fructokinase. In yeast, D-mannose is involved in the metabolic pathway called the mannose metabolism pathway.
Structure
Thumb
Synonyms
  • (+-)-mannose
  • (+)-mannose
  • Carubinose
  • Carubinose (van)
  • D-Mannopyranose
  • D-mannose
  • D(+)-mannose
  • DL-mannose
  • hexose
  • Mannose
  • Mannose (van)
  • Seminose
  • Mannopyranose
  • Mannopyranoside
  • D Mannose
CAS number3458-28-4
WeightAverage: 180.1559
Monoisotopic: 180.063388116
InChI KeyWQZGKKKJIJFFOK-QTVWNMPRSA-N
InChIInChI=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
IUPAC Name(3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Nameβ-glucose
Chemical FormulaC6H12O6
SMILES[H]OC([H])([H])[C@@]1([H])OC([H])(O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting point132 °C
Experimental Properties
PropertyValueReference
Water Solubility713 mg/mL at 17 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility782 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Mannose MetabolismPW002391 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Fructose and mannose metabolismec00051 Map00051
Galactose metabolismec00052 Map00052
SMPDB Reactions
D-Mannose + Adenosine triphosphatehydron + ADP + Mannose 6-phosphate
Adenosine triphosphate + D-MannoseADP + Mannose 6-phosphate
KEGG Reactions
Adenosine triphosphate + D-MannoseD-mannose 6-phosphate + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00kb-1931000000-ec423f92582012821c6aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0fr2-1920000000-b6be17dc79a948dfe5faJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)splash10-00di-9831000000-409527d22fb759cb628fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX)splash10-00di-9621000000-34b421fd962840bfbaecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-066r-1942000000-1c8164b54d2d16c782c3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0ldi-1942000000-c68a088eba727f3a4adaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0mi2-0931000000-96f0cf3c2d4a8bea25b9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-1931000000-ec423f92582012821c6aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-1920000000-b6be17dc79a948dfe5faJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9831000000-409527d22fb759cb628fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-34b421fd962840bfbaecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066r-1942000000-1c8164b54d2d16c782c3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ldi-1942000000-c68a088eba727f3a4adaJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01pc-6900000000-0ef33e32ee16b7803f1bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9000000000-27e169c1df0c3ee59806JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ea-0900000000-9fb0e8db39598c7a269bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c02JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a3518JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a952JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac867JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a36398JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16024
HMDB IDHMDB00169
Pubchem Compound ID18950
Kegg IDC00159
ChemSpider ID23184483
FOODB IDFDB001202
WikipediaMannose
BioCyc IDMANNOSE

Enzymes

General function:
Involved in ATP binding
Specific function:
Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:
HXK2
Uniprot ID:
P04807
Molecular weight:
53942.0
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
Not Available
Uniprot ID:
Q06204
Molecular weight:
48968.80078
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
HXK1
Uniprot ID:
P04806
Molecular weight:
53737.89844
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
General function:
Involved in ATP binding
Specific function:
Putative glucokinase involved in phosphorylation of aldohexoses and glucose uptake. Involved in sporulation. Required for the full activation of the early meiotic inducer IME1
Gene Name:
EMI2
Uniprot ID:
Q04409
Molecular weight:
55920.30078
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
Two isoenzymes, hexokinase-1 and hexokinase-2, can phosphorylate keto- and aldohexoses in yeast, whereas a third isoenzyme, GLK, is specific for aldohexoses. All glucose phosphorylating enzymes are involved in glucose uptake
Gene Name:
GLK1
Uniprot ID:
P17709
Molecular weight:
55376.89844
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.

Transporters

General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT9
Uniprot ID:
P40885
Molecular weight:
62857.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT11
Uniprot ID:
P54862
Molecular weight:
62732.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT10
Uniprot ID:
P43581
Molecular weight:
60661.5
General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity glucose transporter
Gene Name:
HXT6
Uniprot ID:
P39003
Molecular weight:
62704.60156
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT8
Uniprot ID:
P40886
Molecular weight:
63492.0
General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity glucose transporter. Is only indispensable for growth on low glucose-containing media, because S.cerevisiae possesses other sugar transporters
Gene Name:
HXT2
Uniprot ID:
P23585
Molecular weight:
59840.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Low-affinity glucose transporter. HXT1 is as well involved in the transport of mannose
Gene Name:
HXT1
Uniprot ID:
P32465
Molecular weight:
63260.89844
General function:
Involved in transmembrane transporter activity
Specific function:
Low-affinity glucose transporter
Gene Name:
HXT3
Uniprot ID:
P32466
Molecular weight:
62557.19922
General function:
Involved in transmembrane transporter activity
Specific function:
Low-affinity glucose transporter. Can also transport xylose
Gene Name:
HXT4
Uniprot ID:
P32467
Molecular weight:
63909.60156
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT17
Uniprot ID:
P53631
Molecular weight:
62827.69922
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT16
Uniprot ID:
P47185
Molecular weight:
62919.89844
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT5
Uniprot ID:
P38695
Molecular weight:
66251.0
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT13
Uniprot ID:
P39924
Molecular weight:
62733.60156
General function:
Involved in transmembrane transporter activity
Specific function:
Probable glucose transporter
Gene Name:
HXT15
Uniprot ID:
P54854
Molecular weight:
62930.89844
General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity glucose transporter
Gene Name:
HXT7
Uniprot ID:
P39004
Molecular weight:
62734.60156