Common Name

D-Maltose Description

Maltose, or malt sugar, is a primary disaccharide in the human diet formed from two units of glucose joined with an alpha (1->4) linkage. It is the second member of an important biochemical series of glucose chains. The addition of another glucose unit yields maltotriose, Further additions will produce dextrins, also called maltodextrins, and eventually starch. Maltose can be broken down into two glucose moleclies by hydrolysis in living organisms. At the surface of the small intestine, the brush border enzymes maltase, breaks down maltose. (PMID: 14522745 ). Structure

Synonyms

Value Source 4-O-alpha-D-Glucopyranosyl-alpha-D-mannopyranoseChEBI 4-O-a-D-Glucopyranosyl-a-D-mannopyranoseGenerator 4-O-α-D-glucopyranosyl-α-D-mannopyranoseGenerator 1-alpha-D-Glucopyranosyl-4-alpha-D-glucopyranoseHMDB 1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranoseHMDB 4-(alpha-D-glucopyranosido)-alpha-GlucopyranoseHMDB 4-(alpha-D-glucosido)-D-GlucoseHMDB 4-(alpha-delta-glucopyranosido)-alpha-GlucopyranoseHMDB 4-(alpha-delta-glucosido)-delta-GlucoseHMDB 4-O-a-D-Glucopyranosyl-D-glucoseHMDB 4-O-alpha-D-Glucopyranosyl-D-glucopyranoseHMDB 4-O-alpha-D-Glucopyranosyl-D-glucoseHMDB 4-O-alpha-delta-Glucopyranosyl-delta-glucopyranoseHMDB 4-O-alpha-delta-Glucopyranosyl-delta-glucoseHMDB Advantose 100HMDB alpha-D-GLCP-(1->4)-D-GLCPHMDB alpha-D-Glucopyranosyl-(1->4)-D-glucopyranoseHMDB alpha-D-Glucopyranosyl-(1->4)-D-glucoseHMDB alpha-delta-GLCP-(1->4)-delta-GLCPHMDB alpha-delta-Glucopyranosyl-(1->4)-delta-glucopyranoseHMDB alpha-delta-Glucopyranosyl-(1->4)-delta-glucoseHMDB alpha-Malt sugarHMDB CextromaltoseHMDB D-(+)-MaltoseHMDB delta-(+)-MaltoseHMDB delta-MaltoseHMDB FinetoseHMDB Finetose FHMDB MadorosHMDB Malt sugarHMDB MaltobioseHMDB MaltodioseHMDB MaltosHMDB MaltoseHMDB Maltose HHHMDB Maltose HHHHMDB Maltose solutionHMDB MalzzuckerHMDB Martos-10HMDB SunmaltHMDB Sunmalt SHMDB

Chemical Formlia

C12H22O11 Average Molecliar Weight

342.2965 Monoisotopic Molecliar Weight

342.116211546 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 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 CAS Registry Number

69-79-4 SMILES

OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=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

InChI Key

GUBGYTABKSRVRQ-DKBJLJRDSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds Direct Parent

O-glycosyl compounds Alternative Parents

  • Disaccharides
  • Oxanes
  • Secondary alcohols
  • Hemiacetals
  • Polyols
  • Oxacyclic compounds
  • Acetals
  • Primary alcohols
  • Hydrocarbon derivatives
  • Substituents

  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
  • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • alpha-D-glucosyl-(1->4)-D-mannopyranose (CHEBI:47937 )
  • Ontology Status

    Detected and Quantified Origin

  • Drug metabolite
  • Endogenous
  • Biofunction

  • Waste products
  • Application

    Not Available Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Lysosome
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point102 – 103 °CNot Available Boiling PointNot AvailableNot Available Water Solubility780.0 mg/mLNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility586.0 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity68.34 m3·mol-1ChemAxon Polarizability31.43 Å3ChemAxon Number of Rings2ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-01ox-0149000000-74748828832d87932342View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-008c-2950000000-4ebee22b86c2cc9ee3abView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-00kg-9710000000-041dbc580f99b8881518View in MoNA 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 2D NMR

    [1H,1H] 2D NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Lysosome
  • Biofluid Locations

  • Blood
  • Feces
  • Urine
  • Tissue Location

  • Kidney
  • Liver
  • Platelet
  • Pathways

    Name SMPDB Link KEGG Link Glycogen synthetase deficiencySMP00552Not Available Glycogenosis, Type III. Cori disease, Debrancher glycogenosisSMP00553Not Available Glycogenosis, Type IV. Amylopectinosis, Anderson diseaseSMP00554Not Available Glycogenosis, Type VI. Hers diseaseSMP00555Not Available Mucopolysaccharidosis VI. Sly syndromeSMP00556Not Available Starch and Sucrose MetabolismSMP00058map00500 Sucrase-isomaltase deficiencySMP00557Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details FecesDetected but not Quantified Infant (0-1 year old)Both

    Normal

  • 22411374
  • details FecesDetected but not Quantified Not SpecifiedNot Specified

    Normal

  • 20669995
  • details UrineDetected and Quantified16.424 +/- 6.538 umol/mmol creatinineChildren (1 – 13 years old)Not Specified

    Normal

  • Mordechai, Hien, …
  • details UrineDetected and Quantified6.0 (1.3-21.4) umol/mmol creatinineAdlit (>18 years old)Both

    Normal

  • 24023812
  • details UrineDetected and Quantified6.14 +/- 5.12 umol/mmol creatinineInfant (0-1 year old)BothNormal

  • 2026685
  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified1169.0 +/- 526.0 uMAdlit (>18 years old)BothPeritoneal dialysis

  • 15796147
  • details UrineDetected and Quantified8.332 +/- 5.36 umol/mmol creatinineChildren (1 – 13 years old)Not Specified

    Eosinophilic esophagitis

  • Mordechai, Hien, …
  • 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 molecliar weight moleclies 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 IDs

    None External Links DrugBank ID

    DB03323 DrugBank Metabolite ID

    DBMET00495 Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB001193 KNApSAcK ID

    C00001140 Chemspider ID

    9166684 KEGG Compound ID

    C00208 BioCyc ID

    MALTOSE BiGG ID

    34261 Wikipedia Link

    Malt sugar NuGOwiki Link

    HMDB00163 Metagene Link

    HMDB00163 METLIN ID

    413 PubChem Compound

    10991489 PDB ID

    1A7L ChEBI ID

    47937

    Product: Pyrvinium pamoate

    References Synthesis Reference Pedersen, Sven; Vang Hendriksen, Hanne. Method for production of maltose and/or enzymatically modified starch. PCT Int. Appl. (2001), 99 pp. Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Lu J, Willis AC, Reid KB: Purification, characterization and cDNA cloning of human lung surfactant protein D. Biochem J. 1992 Jun 15;284 ( Pt 3):795-802. [PubMed:1339284 ]
    2. Rubaltelli FF, Biadaioli R, Pecile P, Nicoletti P: Intestinal flora in breast- and bottle-fed infants. J Perinat Med. 1998;26(3):186-91. [PubMed:9773376 ]
    3. Andrews RK, Suzuki-Inoue K, Shen Y, Tulasne D, Watson SP, Berndt MC: Interaction of calmodulin with the cytoplasmic domain of platelet glycoprotein VI. Blood. 2002 Jun 1;99(11):4219-21. [PubMed:12010829 ]
    4. Hirooka EY, Muller EE, Freitas JC, Vicente E, Yoshimoto Y, Bergdoll MS: Enterotoxigenicity of Staphylococcus intermedius of canine origin. Int J Food Microbiol. 1988 Dec;7(3):185-91. [PubMed:3275321 ]
    5. Daly JJ, Sherman JK, Green L, Hostetler TL: Survival of Trichomonas vaginalis in human semen. Genitourin Med. 1989 Apr;65(2):106-8. [PubMed:2787774 ]
    6. Sherman JK, Hostetler TL, McHenry K, Daly JJ: Cryosurvival of Trichomonas vaginalis during cryopreservation of human semen. Cryobiology. 1991 Jun;28(3):246-50. [PubMed:1864083 ]
    7. van Leeuwen L: New saccharogenic determination of alpha-amylase in serum and urine. Clin Chem. 1979 Feb;25(2):215-7. [PubMed:215341 ]
    8. Miller LJ, Malagelada JR, Taylor WF, Go VL: Intestinal control of human postprandial gastric function: the role of components of jejunoileal chyme in regulating gastric secretion and gastric emptying. Gastroenterology. 1981 Apr;80(4):763-9. [PubMed:7202948 ]
    9. Roy E, Stavropoulos E, Brennan J, Coade S, Grigorieva E, Walker B, Dagg B, Tascon RE, Lowrie DB, Colston MJ, Jolles S: Therapeutic efficacy of high-dose intravenous immunoglobulin in Mycobacterium tuberculosis infection in mice. Infect Immun. 2005 Sep;73(9):6101-9. [PubMed:16113331 ]
    10. Wyss C, Choi BK, Schupbach P, Guggenheim B, Gobel UB: Treponema maltophilum sp. nov., a small oral spirochete isolated from human periodontal lesions. Int J Syst Bacteriol. 1996 Jul;46(3):745-52. [PubMed:8782684 ]
    11. Morse DR, Schacterle GR, Furst L, Zaydenberg M, Pollack RL: Oral digestion of a complex-carbohydrate cereal: effects of stress and relaxation on physiological and salivary measures. Am J Clin Nutr. 1989 Jan;49(1):97-105. [PubMed:2463752 ]
    12. Yamamoto T, Kajiura S, Hirai Y, Watanabe T: Capnocytophaga haemolytica sp. nov. and Capnocytophaga granulosa sp. nov., from human dental plaque. Int J Syst Bacteriol. 1994 Apr;44(2):324-9. [PubMed:8186098 ]
    13. Zhu J, Marchant RE: Dendritic saccharide surfactant polymers as antifouling interface materials to reduce platelet adhesion. Biomacromolecules. 2006 Apr;7(4):1036-41. [PubMed:16602718 ]
    14. 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 ]
    15. Leth-Larsen R, Holmskov U, Hojrup P: Structural characterization of human and bovine lung surfactant protein D. Biochem J. 1999 Nov 1;343 Pt 3:645-52. [PubMed:10527944 ]
    16. Janoshazi A, Solomon AK: Initial steps of alpha- and beta-D-glucose binding to intact red cell membrane. J Membr Biol. 1993 Mar;132(2):167-78. [PubMed:8496948 ]
    17. Tiwari F, Singh DK: Behavioural responses of the snail Lymnaea acuminata to carbohydrates in snail-attractant pellets. Naturwissenschaften. 2004 Aug;91(8):378-80. Epub 2004 Jun 2. [PubMed:15309310 ]
    18. Chiba S, Hiromi K, Minamiura N, Ohnishi M, Shimomura T, Suga K, Suganuma T, Tanaka A, Tomioka S, Yamamoto T: Quantitative study on anomeric forms of glucose produced by alpha-glucosidases. J Biochem. 1979 May;85(5):1135-41. [PubMed:376499 ]
    19. McCue JP, Hein RH, Tenold R: Three generations of immunoglobulin G preparations for clinical use. Rev Infect Dis. 1986 Jul-Aug;8 Suppl 4:S374-81. [PubMed:3092303 ]
    20. Dorner KM: Quantitative determination of lactose, maltose, and sucrose in urine. Eur J Pediatr. 1977 Aug 23;126(1-2):45-52. [PubMed:902663 ]
    21. Sigman-Grant M, Morita J: Defining and interpreting intakes of sugars. Am J Clin Nutr. 2003 Oct;78(4):815S-826S. [PubMed:14522745 ]

    Enzymes

    General function:
    Involved in catalytic activity
    Specific function:
    Multifunctional enzyme acting as 1,4-alpha-D-glucan:1,4-alpha-D-glucan 4-alpha-D-glycosyltransferase and amylo-1,6-glucosidase in glycogen degradation.
    Gene Name:
    AGL
    Uniprot ID:
    P35573
    Molecular weight:
    Not Available
    General function:
    Involved in catalytic activity
    Specific function:
    Essential for the degradation of glygogen to glucose in lysosomes.
    Gene Name:
    GAA
    Uniprot ID:
    P10253
    Molecular weight:
    Not Available
    Reactions
    D-Maltose + Water → Alpha-D-Glucose details
    General function:
    Involved in catalytic activity
    Specific function:
    Not Available
    Gene Name:
    AMY1A
    Uniprot ID:
    P04745
    Molecular weight:
    Not Available
    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. [PubMed: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. [PubMed: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. [PubMed:10592235 ]
    General function:
    Involved in catalytic activity
    Specific function:
    May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
    Gene Name:
    MGAM
    Uniprot ID:
    O43451
    Molecular weight:
    Not Available
    Reactions
    D-Maltose + Water → Alpha-D-Glucose details
    General function:
    Involved in catalytic activity
    Specific function:
    Has alpha-glucosidase activity.
    Gene Name:
    GANC
    Uniprot ID:
    Q8TET4
    Molecular weight:
    Not Available
    Reactions
    D-Maltose + Water → Alpha-D-Glucose details

    PMID: 10463589