Record Information
Version2.0
Creation Date2012-05-31 13:48:37 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01262
Identification
Name:Maltotriose
DescriptionMaltotriose is a member of the chemical class known as Trihexoses. These are trisaccharides containing three hexose carbohydrates. In E. coli, maltotriose is an intermediate involved in degradation of glycogen to glucose. (Ecocyc)
Structure
Thumb
Synonyms:
  • 4-O-(4-O-Hexopyranosylhexopyranosyl)hexose
  • Amylotriose
  • D-(+)-Maltotriose
  • Delta-(+)-Maltotriose
  • Maltotriose
  • O-a-D-Glucopyranosyl-(1b94)-O-a-D-glucopyranosyl-(1b94)-O-a-D-glucose
  • O-a-delta-Glucopyranosyl-(1b94)-O-a-delta-glucopyranosyl-(1b94)-O-a-delta-glucose
  • O-a-δ-Glucopyranosyl-(1b94)-O-a-δ-glucopyranosyl-(1b94)-O-a-δ-glucose
  • O-alpha-D-Glucopyranosyl-(1beta94)-O-alpha-D-glucopyranosyl-(1beta94)-O-alpha-D-glucose
  • O-alpha-delta-Glucopyranosyl-(1beta94)-O-alpha-delta-glucopyranosyl-(1beta94)-O-alpha-delta-glucose
  • O-α-D-Glucopyranosyl-(1β94)-O-α-D-glucopyranosyl-(1β94)-O-α-D-glucose
  • O-α-δ-Glucopyranosyl-(1β94)-O-α-δ-glucopyranosyl-(1β94)-O-α-δ-glucose
  • δ-(+)-Maltotriose
Chemical Formula:C18H32O16
Weight:Average: 504.4371
Monoisotopic: 504.169034976
InChI Key:FYGDTMLNYKFZSV-DZOUCCHMSA-N
InChI:InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16?,17-,18-/m1/s1
CAS number:1109-28-0
IUPAC Name:(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional IUPAC Name:maltotriose
SMILES:OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)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 oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-8.004PhysProp
Predicted Properties
PropertyValueSource
Water Solubility554 g/LALOGPS
logP-2.7ALOGPS
logP-6.5ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)11.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.75 m³·mol⁻¹ChemAxon
Polarizability46.65 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Porphyrin and chlorophyll metabolism ec00860
  • Starch and sucrose metabolism ec00500
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS)splash10-0uxr-0961000000-eedb43ec0d980ce3b6dcView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS)splash10-0uxr-0961000000-f2a522371c62148c925cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxr-0972000000-ea64ef22a740ff6d7271View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udj-0972000000-4b10e9ea754fa393dc86View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS; 1 MEOX)splash10-0fk9-9871000000-3de822f1f079a12db963View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (11 TMS; 1 MEOX)splash10-0fk9-9872000000-b2e2130ce45ac4ccf4aeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0961000000-beca1052fe892464807dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0971000000-f313bd9a2aaaf17d79d8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-2321900000-2c06af6e8c61473ee773View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00sr-8325139000-e740f833d097d25517baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0309000000-4045fdf8a9069c4881c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03ds-4900000000-f4d71bfee642eb6d42d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9300000000-1c2e73b0b7042f4defbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0ir0-5911000000-c2aba069e7ab6ddbefa6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0h90-5911000000-c6cda5cae8a5bd10ca18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06vu-0509520000-77aa8a8f584bac3d49c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0809000000-474431b9d89ea66d1b1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-1912100000-0e7fa2b5d3f11f84c425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udr-0536960000-3a949257e44159506dbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bi-2915300000-b1a137d1e16f6457e14bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3921000000-7390c3ce452a4426fd64View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lingstrom P, Birkhed D, Granfeldt Y, Bjorck I: pH measurements of human dental plaque after consumption of starchy foods using the microtouch and the sampling method. Caries Res. 1993;27(5):394-401. Pubmed: 8242677
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yuge O, Morio M, Fukui T, Fujii K, Kikuchi H, Takahashi S: Maltotriose and maltotetraose excreted in urine following intravenous administration of maltose to human volunteers. Jpn J Surg. 1983 Jul;13(4):296-303. Pubmed: 6645121
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID27931
HMDB IDHMDB01262
Pubchem Compound ID439586
Kegg IDC01835
ChemSpider ID388669
Wikipedia IDMaltotriose
BioCyc IDMALTOTRIOSE
EcoCyc IDMALTOTRIOSE

Enzymes

General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
Gene Name:
malP
Uniprot ID:
P00490
Molecular weight:
90522
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.
General function:
Involved in 4-alpha-glucanotransferase activity
Specific function:
Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan
Gene Name:
malQ
Uniprot ID:
P15977
Molecular weight:
78503
Reactions
Transfers a segment of a (1->4)-alpha-D-glucan to a new position in an acceptor, which may be glucose or a (1->4)-alpha-D-glucan.
General function:
Involved in catalytic activity
Specific function:
May play a role in regulating the intracellular level of maltotriose. Cleaves glucose from the reducing end of maltotriose and longer maltodextrins with a chain length of up to 7 glucose units
Gene Name:
malZ
Uniprot ID:
P21517
Molecular weight:
69172
Reactions
Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of alpha-D-glucose.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
Gene Name:
malK
Uniprot ID:
P68187
Molecular weight:
40990
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
Gene Name:
malF
Uniprot ID:
P02916
Molecular weight:
57013
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
Gene Name:
malG
Uniprot ID:
P68183
Molecular weight:
32225
General function:
Involved in maltose transmembrane transporter activity
Specific function:
Involved in the high-affinity maltose membrane transport system malEFGK. Initial receptor for the active transport of and chemotaxis toward maltooligosaccharides
Gene Name:
malE
Uniprot ID:
P0AEX9
Molecular weight:
43387

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex MalEFGK involved in maltose/maltodextrin import. Responsible for energy coupling to the transport system
Gene Name:
malK
Uniprot ID:
P68187
Molecular weight:
40990
Reactions
ATP + H(2)O + maltose(Out) = ADP + phosphate + maltose(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
Gene Name:
malF
Uniprot ID:
P02916
Molecular weight:
57013
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for maltose; probably responsible for the translocation of the substrate across the membrane
Gene Name:
malG
Uniprot ID:
P68183
Molecular weight:
32225
General function:
Involved in maltose transmembrane transporter activity
Specific function:
Involved in the high-affinity maltose membrane transport system malEFGK. Initial receptor for the active transport of and chemotaxis toward maltooligosaccharides
Gene Name:
malE
Uniprot ID:
P0AEX9
Molecular weight:
43387
General function:
Involved in porin activity
Specific function:
Involved in the transport of maltose and maltodextrins, indispensable for translocation of dextrins containing more than three glucosyl moieties. A hydrophobic path ("greasy slide") of aromatic residues serves to guide and select the sugars for transport through the channel. Also acts as a receptor for several bacteriophages including lambda
Gene Name:
lamB
Uniprot ID:
P02943
Molecular weight:
49912