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Identification
YMDB IDYMDB00584
NameMaltose
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Maltose, also known as alpha-malt sugar or cextromaltose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. D-Maltose is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Maltose exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 1-alpha-d-glucopyranosyl-4-alpha-d-glucopyranose
  • 1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranose
  • 4-(alpha-D-glucopyranosido)-alpha-glucopyranose
  • 4-(alpha-D-glucosido)-D-glucose
  • 4-(alpha-delta-glucopyranosido)-alpha-glucopyranose
  • 4-(alpha-delta-glucosido)-delta-glucose
  • 4-O-a-D-Glucopyranosyl-D-glucose
  • 4-O-alpha-D-glucopyranosyl-D-glucopyranose
  • 4-O-alpha-D-glucopyranosyl-D-glucose
  • 4-O-alpha-delta-glucopyranosyl-delta-glucopyranose
  • 4-O-alpha-delta-glucopyranosyl-delta-glucose
  • 4-O-Hexopyranosylhexose
  • alpha-D-Glcp-(1->4)-D-Glcp
  • alpha-D-glucopyranosyl-(1->4)-D-glucopyranose
  • alpha-D-glucopyranosyl-(1->4)-D-glucose
  • alpha-delta-Glcp-(1->4)-delta-Glcp
  • alpha-delta-glucopyranosyl-(1->4)-delta-glucopyranose
  • alpha-delta-glucopyranosyl-(1->4)-delta-glucose
  • alpha-Malt sugar
  • Cextromaltose
  • D-(+)-maltose
  • D-Maltose
  • delta-(+)-maltose
  • delta-Maltose
  • Finetose
  • Finetose F
  • Madoros
  • Madoros (TN)
  • malt sugar
  • Maltobiose
  • Maltodiose
  • Maltos
  • Maltose
  • Maltose (NF)
  • Maltose HH
  • Maltose HHH
  • Maltose solution
  • Malzzucker
  • Martos-10
  • Sunmalt
  • Sunmalt S
  • 4-O-alpha-D-Glucopyranosyl-alpha-D-mannopyranose
  • 4-O-a-D-Glucopyranosyl-a-D-mannopyranose
  • 4-O-Α-D-glucopyranosyl-α-D-mannopyranose
  • Advantose 100
CAS number69-79-4
WeightAverage: 342.2965
Monoisotopic: 342.116211546
InChI KeyGUBGYTABKSRVRQ-PICCSMPSSA-N
InChIInChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11?,12-/m1/s1
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
Traditional IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
Chemical FormulaC12H22O11
SMILESOC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point102-103 °C
Experimental Properties
PropertyValueReference
Water Solubility780 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility586 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)11.25ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB001193
SMPDB Pathways
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
MaltoseAlpha-D-Glucose
MaltoseAlpha-D-Glucose
KEGG Reactions
Maltose + waterD-Glucose
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-4897000000-332d470623cd7f1e1cedJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-3421129000-03a98898fd3278f95502JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0149000000-74748828832d87932342JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-008c-2950000000-4ebee22b86c2cc9ee3abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kg-9710000000-041dbc580f99b8881518JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03gl-0907000000-a1de7813fbe8b5258c10JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-0900000000-79cc5059a3f338e8c1ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-851d0bc84d91b6e09579JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0749000000-af1d18f2bc3ab8e02883JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-2902000000-67218697344afb9e70faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01td-4900000000-40aa2d8125769803cfbbJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Serrano, R. (1977). "Energy requirements for maltose transport in yeast." Eur J Biochem 80:97-102.21792
  • 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:Pedersen, Sven; Vang Hendriksen, Hanne. Method for production of maltose and/or enzymatically modified starch. PCT Int. Appl. (2001), 99 pp.
External Links:
ResourceLink
CHEBI ID17306
HMDB IDHMDB00163
Pubchem Compound ID439186
Kegg IDC00208
ChemSpider ID23327704
FOODB IDFDB001193
WikipediaMaltose
BioCyc IDMALTOSE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Hydrolysis of terminal, non-reducing (1->4)- linked alpha-D-glucose residues with release of alpha-D-glucose
Gene Name:
MAL32
Uniprot ID:
P38158
Molecular weight:
68141.79688
Reactions
General function:
Involved in catalytic activity
Specific function:
Catalytic subunit of glucosidase 2, which cleaves sequentially the 2 innermost alpha-1,3-linked glucose residues from the Glc(2)Man(9)GlcNAc(2) oligosaccharide precursor of immature glycoproteins
Gene Name:
ROT2
Uniprot ID:
P38138
Molecular weight:
110265.0
Reactions
General function:
Involved in catalytic activity
Specific function:
Hydrolysis of terminal, non-reducing (1->4)- linked alpha-D-glucose residues with release of alpha-D-glucose
Gene Name:
MAL12
Uniprot ID:
P53341
Molecular weight:
68093.70313
Reactions
General function:
Carbohydrate transport and metabolism
Specific function:
Probable alpha-glucosidase involved in maltose metabolism
Gene Name:
Not Available
Uniprot ID:
P40439
Molecular weight:
68698.10156
General function:
Involved in catalytic activity
Specific function:
Hydrolysis of terminal, non-reducing (1->4)- linked alpha-D-glucose residues with release of alpha-D-glucose
Gene Name:
MAL62
Uniprot ID:
P07265
Molecular weight:
68182.79688
General function:
Involved in catalytic activity
Specific function:
Preferentially hydrolyzes isomaltose, with little activity towards isomaltotriose or longer oligosaccharides. Does not hydrolyze maltose
Gene Name:
FSP2
Uniprot ID:
P53051
Molecular weight:
68591.0
Reactions

Transporters

General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity uptake of alpha-glucosides such as maltose, turanose, isomaltose, alpha-methylglucoside, maltotriose, palatinose, trehalose, melezitose and glucose. Acts with the concomitant transport of protons into the cell (symport system)
Gene Name:
MAL11
Uniprot ID:
P53048
Molecular weight:
67979.60156
General function:
Involved in transmembrane transporter activity
Specific function:
High-affinity uptake of maltose and maltotriose. Also transports turanose but not alpha-methylglucoside, melezitose or trehalose
Gene Name:
MAL31
Uniprot ID:
P38156
Molecular weight:
68262.20313