Identification
NameMaltose
Accession NumberDB03323  (EXPT02111)
TypeSmall Molecule
GroupsExperimental
Description

A dextrodisaccharide from malt and starch. It is used as a sweetening agent and fermentable intermediate in brewing. (Grant & Hackh's Chemical Dictionary, 5th ed)

Structure
Thumb
Synonyms
D-(+)-maltose
Maltose anhydrous
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII66Y63L379N
CAS number69-79-4
WeightAverage: 342.2965
Monoisotopic: 342.116211546
Chemical FormulaC12H22O11
InChI KeyGUBGYTABKSRVRQ-PICCSMPSSA-N
InChI
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
IUPAC Name
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol
SMILES
OC[[email protected]]1O[[email protected]](O[[email protected]]2[[email protected]](O)[C@@H](O)C(O)O[C@@H]2CO)[[email protected]](O)[C@@H](O)[C@@H]1O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Cyclomaltodextrin glucanotransferaseProteinunknownNot AvailableBacillus circulansP30920 details
Alpha-amylase 2BProteinunknownNot AvailableHumanP19961 details
Beta-amylaseProteinunknownNot AvailableBacillus cereusP36924 details
Maltogenic alpha-amylaseProteinunknownNot AvailableGeobacillus stearothermophilusP19531 details
Maltodextrin phosphorylaseProteinunknownNot AvailableEscherichia coli (strain K12)P00490 details
Maltose-binding periplasmic proteinProteinunknownNot AvailableEscherichia coli (strain K12)P0AEX9 details
Alpha-glucosidaseProteinunknownNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)O33830 details
Maltose binding proteinProteinunknownNot AvailableAlicyclobacillus acidocaldariusQ9RHZ6 details
Malto-oligosyltrehalose trehalohydrolaseProteinunknownNot AvailableDeinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)Q9RX51 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Glycogen synthetase deficiencyDiseaseSMP00552
Glycogenosis, Type VI. Hers diseaseDiseaseSMP00555
Sucrase-isomaltase deficiencyDiseaseSMP00557
Starch and Sucrose MetabolismMetabolicSMP00058
Glycogenosis, Type IV. Amylopectinosis, Anderson diseaseDiseaseSMP00554
Glycogenosis, Type III. Cori disease, Debrancher glycogenosisDiseaseSMP00553
Mucopolysaccharidosis VI. Sly syndromeDiseaseSMP00556
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

Chobe Yomoto, Takashi Adachi, Yutaka Nakajima, Hidemasa Hidaka, Tsukasa Yoshida, Fumio Sugawara, "Method for producing maltose." U.S. Patent US3998696, issued May, 1971.

US3998696
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentAutism Spectrum Disorder (ASD) / Feeling Anxious1
1, 2RecruitingTreatmentCancers / Neoplasms / Tumors1
3RecruitingTreatmentBipolar Disorder (BD) / Depression, Bipolar1
Not AvailableCompletedTreatmentVascular Aging1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)102-103 °CPhysProp
water solubility7.8E+005 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
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
Polarizability31.57 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8748
Blood Brain Barrier+0.6207
Caco-2 permeable-0.8836
P-glycoprotein substrateNon-substrate0.5394
P-glycoprotein inhibitor INon-inhibitor0.7589
P-glycoprotein inhibitor IINon-inhibitor0.9142
Renal organic cation transporterNon-inhibitor0.8144
CYP450 2C9 substrateNon-substrate0.8451
CYP450 2D6 substrateNon-substrate0.8853
CYP450 3A4 substrateNon-substrate0.658
CYP450 1A2 substrateNon-inhibitor0.961
CYP450 2C9 inhibitorNon-inhibitor0.9376
CYP450 2D6 inhibitorNon-inhibitor0.9399
CYP450 2C19 inhibitorNon-inhibitor0.9083
CYP450 3A4 inhibitorNon-inhibitor0.9645
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8898
Ames testNon AMES toxic0.8628
CarcinogenicityNon-carcinogens0.9551
BiodegradationNot ready biodegradable0.6632
Rat acute toxicity1.0242 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9517
hERG inhibition (predictor II)Non-inhibitor0.8283
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
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
Taxonomy
DescriptionThis 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-glycosyl compounds
Alternative ParentsDisaccharides / Oxanes / Secondary alcohols / Hemiacetals / Polyols / Oxacyclic compounds / Acetals / Primary alcohols / Hydrocarbon derivatives
SubstituentsO-glycosyl compound / Disaccharide / Oxane / Secondary alcohol / Hemiacetal / Oxacycle / Organoheterocyclic compound / Polyol / Acetal / Hydrocarbon derivative
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptorsglycosylglucose, maltooligosaccharide (CHEBI:17306 ) / Disaccharides (C00208 )

Targets

Kind
Protein
Organism
Bacillus circulans
Pharmacological action
unknown
General Function:
Starch binding
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P30920
Uniprot Name:
Cyclomaltodextrin glucanotransferase
Molecular Weight:
78046.265 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Alpha-amylase activity
Gene Name:
AMY2B
Uniprot ID:
P19961
Uniprot Name:
Alpha-amylase 2B
Molecular Weight:
57709.49 Da
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 ]
Kind
Protein
Organism
Bacillus cereus
Pharmacological action
unknown
General Function:
Starch binding
Specific Function:
Not Available
Gene Name:
spoII
Uniprot ID:
P36924
Uniprot Name:
Beta-amylase
Molecular Weight:
61628.585 Da
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 ]
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
unknown
General Function:
Starch binding
Specific Function:
Converts starch into maltose.
Gene Name:
amyM
Uniprot ID:
P19531
Uniprot Name:
Maltogenic alpha-amylase
Molecular Weight:
78675.13 Da
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 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Pyridoxal phosphate binding
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
Uniprot Name:
Maltodextrin phosphorylase
Molecular Weight:
90521.74 Da
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 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
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
Uniprot Name:
Maltose-binding periplasmic protein
Molecular Weight:
43387.235 Da
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 ]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
unknown
General Function:
Oxidoreductase activity, acting on the ch-oh group of donors, nad or nadp as acceptor
Specific Function:
Alpha-glycosidase with a very broad specificity. Hydrolyzes maltose and other small maltooligosaccharides but is inactive against the polymeric substrate starch. AglA is not specific with respect to the configuration at the C-4 position of its substrates because glycosidic derivatives of D-galactose are also hydrolyzed. Does not cleave beta-glycosidic bonds.
Gene Name:
aglA
Uniprot ID:
O33830
Uniprot Name:
Alpha-glucosidase
Molecular Weight:
55046.815 Da
Kind
Protein
Organism
Alicyclobacillus acidocaldarius
Pharmacological action
unknown
General Function:
Maltose transmembrane transporter activity
Specific Function:
Not Available
Gene Name:
malE
Uniprot ID:
Q9RHZ6
Uniprot Name:
Maltose binding protein
Molecular Weight:
45673.62 Da
Kind
Protein
Organism
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Pharmacological action
unknown
General Function:
Cation binding
Specific Function:
Not Available
Gene Name:
treZ
Uniprot ID:
Q9RX51
Uniprot Name:
Malto-oligosyltrehalose trehalohydrolase
Molecular Weight:
66909.235 Da
Drug created on June 13, 2005 07:24 / Updated on June 11, 2017 20:46