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
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2015-03-09 22:57:02 UTC
HMDB IDHMDB00163
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Maltose
DescriptionMaltose, 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 molecules by hydrolysis in living organisms. At the surface of the small intestine, the brush border enzymes maltase, breaks down maltose. (PMID: 14522745 ).
Structure
Thumb
Synonyms
  1. 1-alpha-D-Glucopyranosyl-4-alpha-D-glucopyranose
  2. 1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranose
  3. 4-(alpha-D-Glucopyranosido)-alpha-glucopyranose
  4. 4-(alpha-D-Glucosido)-D-glucose
  5. 4-(alpha-delta-Glucopyranosido)-alpha-glucopyranose
  6. 4-(alpha-delta-Glucosido)-delta-glucose
  7. 4-O-a-D-Glucopyranosyl-D-glucose
  8. 4-O-alpha-D-Glucopyranosyl-D-glucopyranose
  9. 4-O-alpha-D-Glucopyranosyl-D-glucose
  10. 4-O-alpha-delta-Glucopyranosyl-delta-glucopyranose
  11. 4-O-alpha-delta-Glucopyranosyl-delta-glucose
  12. Advantose 100
  13. alpha-D-Glcp-(1->4)-D-Glcp
  14. alpha-D-Glucopyranosyl-(1->4)-D-glucopyranose
  15. alpha-D-Glucopyranosyl-(1->4)-D-glucose
  16. alpha-delta-Glcp-(1->4)-delta-Glcp
  17. alpha-delta-Glucopyranosyl-(1->4)-delta-glucopyranose
  18. alpha-delta-Glucopyranosyl-(1->4)-delta-glucose
  19. alpha-Malt sugar
  20. Cextromaltose
  21. D-(+)-Maltose
  22. D-Maltose
  23. delta-(+)-Maltose
  24. delta-Maltose
  25. Finetose
  26. Finetose F
  27. Madoros
  28. Madoros (TN)
  29. Malt sugar
  30. Maltobiose
  31. Maltodiose
  32. Maltos
  33. Maltose
  34. Maltose HH
  35. Maltose HHH
  36. Maltose solution
  37. Malzzucker
  38. Martos-10
  39. Sunmalt
  40. Sunmalt S
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
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 Number69-79-4
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 KeyInChIKey=GUBGYTABKSRVRQ-DKBJLJRDSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • 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 Descriptors
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 Point102 - 103 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility780.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified6.0 (1.3-21.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.14 +/- 5.12 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1169.0 +/- 526.0 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 IDDB03323
DrugBank Metabolite IDDBMET00495
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001193
KNApSAcK IDC00001140
Chemspider ID9166684
KEGG Compound IDC00208
BioCyc IDMALTOSE
BiGG ID34261
Wikipedia LinkMalt sugar
NuGOwiki LinkHMDB00163
Metagene LinkHMDB00163
METLIN ID413
PubChem Compound10991489
PDB ID1A7L
ChEBI ID47937
References
Synthesis ReferencePedersen, 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. [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. [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. [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. [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. [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. [1864083 ]
  7. van Leeuwen L: New saccharogenic determination of alpha-amylase in serum and urine. Clin Chem. 1979 Feb;25(2):215-7. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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 (Tokyo). 1979 May;85(5):1135-41. [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. [3092303 ]
  20. Dorner KM: Quantitative determination of lactose, maltose, and sucrose in urine. Eur J Pediatr. 1977 Aug 23;126(1-2):45-52. [902663 ]
  21. Sigman-Grant M, Morita J: Defining and interpreting intakes of sugars. Am J Clin Nutr. 2003 Oct;78(4):815S-826S. [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-Glucosedetails
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. [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 ]
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-Glucosedetails
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-Glucosedetails