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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:07 UTC
HMDB IDHMDB01262
Secondary Accession NumbersNone
Metabolite Identification
Common NameMaltotriose
DescriptionMaltotriose is a common oligosaccharide metabolite found in human urine after maltose ingestion or infusion (PMID 6645121 ). Maltotriose is increased in Glycogen storage disease II (OMIM 232300 ) due to a mutation of the enzyme alpha-1,4-glucosidase (E.C. 3.2.1.20) (4286143).
Structure
Thumb
Synonyms
ValueSource
AmylotrioseKegg
4-O-(4-O-Hexopyranosylhexopyranosyl)hexoseHMDB
D-(+)-MaltotrioseHMDB
delta-(+)-MaltotrioseHMDB
O-alpha-D-Glucopyranosyl-(1beta94)-O-alpha-D-glucopyranosyl-(1beta94)-O-alpha-D-glucoseHMDB
O-alpha-delta-Glucopyranosyl-(1beta94)-O-alpha-delta-glucopyranosyl-(1beta94)-O-alpha-delta-glucoseHMDB
Chemical FormulaC18H32O16
Average Molecular Weight504.4371
Monoisotopic Molecular Weight504.169034976
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 Namemaltotriose
CAS Registry Number1109-28-0
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
InChI Identifier
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
InChI KeyInChIKey=FYGDTMLNYKFZSV-DZOUCCHMSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassOligosaccharides
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Lysosome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility554.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.75 m3·mol-1ChemAxon
Polarizability46.65 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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)splash10-0uxr-0972000000-ea64ef22a740ff6d7271View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)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
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified257.0 +/- 218.0 uMAdult (>18 years old)BothPeritoneal dialysis details
Associated Disorders and Diseases
Disease References
Peritoneal dialysis
  1. Garcia-Lopez E, Anderstam B, Heimburger O, Amici G, Werynski A, Lindholm B: Determination of high and low molecular weight molecules of icodextrin in plasma and dialysate, using gel filtration chromatography, in peritoneal dialysis patients. Perit Dial Int. 2005 Mar-Apr;25(2):181-91. [15796147 ]
Associated OMIM IDsNone
DrugBank IDDB03277
DrugBank Metabolite IDDBMET00523
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001196
KNApSAcK IDNot Available
Chemspider ID388669
KEGG Compound IDC01835
BioCyc IDMALTOTRIOSE
BiGG ID38512
Wikipedia LinkMaltotriose
NuGOwiki LinkHMDB01262
Metagene LinkHMDB01262
METLIN ID3585
PubChem Compound439586
PDB ID1UA3
ChEBI ID27931
References
Synthesis ReferenceWallenfels, Kurt; Bender, Hans. Maltotriose. (1965), 2 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [19212411 ]
  2. 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. [8242677 ]
  3. 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. [6645121 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY2B
Uniprot ID:
P19961
Molecular weight:
Not Available
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]