You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-21 18:16:27 UTC
HMDB IDHMDB0001296
Secondary Accession Numbers
  • HMDB01296
StatusDetected and Quantified
Metabolite Identification
Common NameMaltotetraose
DescriptionMaltotetraose is a normal human oligo saccharide present in plasma, but is elevated in cases of Pompe disease (PMID 15886040 ).
Structure
Thumb
Synonyms
ValueSource
alpha-1,4-TetraglucoseHMDB
AmylotetraoseHMDB
O-alpha-D-Glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-glucoseHMDB
O-alpha-D-Glucopyranosyl-(1->4)-O(4xi)-alpha-D-xylo-hexopyranosyl-(1->4)-O-alpha-D-glucopyranosyl-(1->4)-D-glucoseHMDB
O-alpha-D-Glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-D-glucoseHMDB
O-alpha-delta-Glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-delta-glucoseHMDB
O-alpha-delta-Glucopyranosyl-(1->4)-O(4xi)-alpha-delta-xylo-hexopyranosyl-(1->4)-O-alpha-delta-glucopyranosyl-(1->4)-delta-glucoseHMDB
O-alpha-delta-Glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-delta-glucoseHMDB
Chemical FormulaC24H42O21
Average Molecular Weight666.5777
Monoisotopic Molecular Weight666.221858406
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(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}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(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}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry Number34612-38-9
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@@H](O[C@H]4[C@H](O)[C@@H](O)C(O)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C24H42O21/c25-1-5-9(29)10(30)15(35)22(40-5)44-19-7(3-27)42-24(17(37)12(19)32)45-20-8(4-28)41-23(16(36)13(20)33)43-18-6(2-26)39-21(38)14(34)11(18)31/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21?,22-,23-,24-/m1/s1
InChI KeyLUEWUZLMQUOBSB-AYQJAVFRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Health effect:
Health condition:
Disposition
Biological Location:
Subcellular:
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 Solubility350.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-8.2ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)11.19ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area347.83 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity133.16 m3·mol-1ChemAxon
Polarizability62.18 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-002r-0109714000-92449118dd9f88ced9e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0902000000-bada4f81875480cef630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03ds-4900000000-8c70af31defdcfbbdaceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Prostate
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineExpected but not Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified375.0 +/- 345.0 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. [PubMed:15796147 ]
    Associated OMIM IDsNone
    DrugBank IDDB02237
    DrugBank Metabolite IDDBMET00525
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB001195
    KNApSAcK IDC00018031
    Chemspider ID388711
    KEGG Compound IDC02052
    BioCyc IDMALTOTETRAOSE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0001296
    METLIN ID4199
    PubChem Compound439639
    PDB ID1JIB
    ChEBI ID61988
    References
    Synthesis ReferenceZhu, Ming. Production of maltotetraose. Wuxi Qinggong Daxue Xuebao (1999), 18(2), 7-12.
    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. doi: 10.1038/nature07762. [PubMed:19212411 ]
    2. 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 ]
    3. Dewit O, Dibba B, Prentice A: Breast-milk amylase activity in English and Gambian mothers: effects of prolonged lactation, maternal parity, and individual variations. Pediatr Res. 1990 Nov;28(5):502-6. [PubMed:1701531 ]
    4. An Y, Young SP, Kishnani PS, Millington DS, Amalfitano A, Corz D, Chen YT: Glucose tetrasaccharide as a biomarker for monitoring the therapeutic response to enzyme replacement therapy for Pompe disease. Mol Genet Metab. 2005 Aug;85(4):247-54. [PubMed:15886040 ]
    5. Kuriyama M, Hiwatari R, Osame M, Igata A: Leucocyte alpha-1,4- and alpha-1,6-glucosidase activities towards oligosaccharides in late onset glycogenosis type II. Tohoku J Exp Med. 1990 Aug;161(4):343-51. [PubMed:2256108 ]
    6. Whitlow KJ, Gochman N, Forrester RL, Wataji LJ: Maltotetraose as a substrate for enzyme-coupled assay of amylase activity in serum and urine. Clin Chem. 1979 Mar;25(3):481-3. [PubMed:95558 ]