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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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("D-Maltose,3TBDMS,#3" TMS) - 70eV, PositiveNot AvailableJSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0109000000-9d0f9a68a67bafd734abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01rw-3898000000-7f495a1bcfdbed6466c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-9210000000-b8a83657f0266d372beeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1069000000-9cd867711bca0eecf935JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9365000000-65403961bfb5e35eaa0dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9200000000-0de9785c1c5df1430dd2JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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