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Identification
NameSucrose
Accession NumberDB02772  (EXPT02977)
TypeSmall Molecule
GroupsExperimental
Description

A nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane, sugar beet (beta vulgaris), and other plants and used extensively as a food and a sweetener. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number57-50-1
WeightAverage: 342.2965
Monoisotopic: 342.116211546
Chemical FormulaC12H22O11
InChI KeyCZMRCDWAGMRECN-MTNNYNCSSA-N
InChI
InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12+/m0/s1
IUPAC Name
(2R,3S,4R,5R,6S)-2-{[(2R,3R,4R,5S)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES
OC[C@@H]1O[C@](CO)(O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassDisaccharides
Direct parentMixed Pentose/Hexose Disaccharides
Alternative parentsC-glycosyl Compounds; O-glycosyl Compounds; Oxanes; Tetrahydrofurans; Oxolanes; 1,2-Diols; Secondary Alcohols; Primary Alcohols; Acetals; Polyamines
Substituentsc-glycosyl compound; glycosyl compound; o-glycosyl compound; oxane; tetrahydrofuran; oxolane; polyol; secondary alcohol; 1,2-diol; primary alcohol; ether; acetal; polyamine; alcohol
Classification descriptionThis compound belongs to the mixed pentose/hexose disaccharides. These are disaccharides containing both an hexose and a pentose.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.8682
Blood Brain Barrier + 0.7245
Caco-2 permeable - 0.8957
P-glycoprotein substrate Non-substrate 0.6386
P-glycoprotein inhibitor I Non-inhibitor 0.8721
P-glycoprotein inhibitor II Non-inhibitor 0.9402
Renal organic cation transporter Non-inhibitor 0.8146
CYP450 2C9 substrate Non-substrate 0.8747
CYP450 2D6 substrate Non-substrate 0.8561
CYP450 3A4 substrate Non-substrate 0.6536
CYP450 1A2 substrate Non-inhibitor 0.9425
CYP450 2C9 substrate Non-inhibitor 0.9377
CYP450 2D6 substrate Non-inhibitor 0.9395
CYP450 2C19 substrate Non-inhibitor 0.8821
CYP450 3A4 substrate Non-inhibitor 0.9716
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9258
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.9565
Biodegradation Not ready biodegradable 0.7256
Rat acute toxicity 1.0936 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9633
hERG inhibition (predictor II) Non-inhibitor 0.883
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point185.5 °CPhysProp
water solubility2.1E+006 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.70HANSCH,C ET AL. (1995)
Caco2 permeability-5.77ADME Research, USCD
pKa12.6MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility824.0ALOGPS
logP-2.6ALOGPS
logP-4.5ChemAxon
logS0.38ALOGPS
pKa (Strongest Acidic)11.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.77 m3·mol-1ChemAxon
Polarizability31.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Francois B. Paul, Pierre F. Monsan, Magali M. C. Remaud, Vincent P. Pelenc, “Process for the enzymatic preparation from sucrose of a mixture of sugars having a high content of isomaltose, and products obtained.” U.S. Patent US4861381, issued April, 1956.

US4861381
General Reference
  1. Ten S, Maclaren N: Insulin resistance syndrome in children. J Clin Endocrinol Metab. 2004 Jun;89(6):2526-39. Pubmed
  2. Aguilera AA, Diaz GH, Barcelata ML, Guerrero OA, Ros RM: Effects of fish oil on hypertension, plasma lipids, and tumor necrosis factor-alpha in rats with sucrose-induced metabolic syndrome. J Nutr Biochem. 2004 Jun;15(6):350-7. Pubmed
  3. Fukuchi S, Hamaguchi K, Seike M, Himeno K, Sakata T, Yoshimatsu H: Role of fatty acid composition in the development of metabolic disorders in sucrose-induced obese rats. Exp Biol Med (Maywood). 2004 Jun;229(6):486-93. Pubmed
  4. Lombardo YB, Drago S, Chicco A, Fainstein-Day P, Gutman R, Gagliardino JJ, Gomez Dumm CL: Long-term administration of a sucrose-rich diet to normal rats: relationship between metabolic and hormonal profiles and morphological changes in the endocrine pancreas. Metabolism. 1996 Dec;45(12):1527-32. Pubmed
External Links
ResourceLink
KEGG DrugD00025
KEGG CompoundC00089
PubChem Compound46936484
PubChem Substance46506134
ChEBI17992
ChEMBL
PharmGKBPA451525
HETSUC
Drug Product Database50121
RxListhttp://www.rxlist.com/cgi/generic/venofer.htm
WikipediaSucrose
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Beta-glucosidase

Kind: protein

Organism: Streptomyces sp.

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-glucosidase Q59976 Details

2. Amylosucrase

Kind: protein

Organism: Neisseria polysaccharea

Pharmacological action: unknown

Components

Name UniProt ID Details
Amylosucrase Q9ZEU2 Details

3. Beta-lactamase

Kind: protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-lactamase Q9L5C8 Details

4. Beta-lactamase CTX-M

Kind: protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-lactamase CTX-M Q9L5C7 Details

5. Heme oxygenase

Kind: protein

Organism: Corynebacterium diphtheriae (strain ATCC 700971 / NCTC 13129 / Biotype gravis)

Pharmacological action: unknown

Components

Name UniProt ID Details
Heme oxygenase P71119 Details

6. Copper transport protein ATOX1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Copper transport protein ATOX1 O00244 Details

7. tRNA-splicing ligase RtcB homolog

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
tRNA-splicing ligase RtcB homolog Q9Y3I0 Details

References:

  1. 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

8. Orange carotenoid-binding protein

Kind: protein

Organism: Arthrospira maxima

Pharmacological action: unknown

Components

Name UniProt ID Details
Orange carotenoid-binding protein P83689 Details

9. Sucrose porin

Kind: protein

Organism: Salmonella typhimurium

Pharmacological action: unknown

Components

Name UniProt ID Details
Sucrose porin P22340 Details

10. Levansucrase

Kind: protein

Organism: Bacillus subtilis (strain 168)

Pharmacological action: unknown

Components

Name UniProt ID Details
Levansucrase P05655 Details

11. Beta-lactamase CTX-M-27

Kind: protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-lactamase CTX-M-27 Q840M4 Details

12. GDP-mannose 6-dehydrogenase

Kind: protein

Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)

Pharmacological action: unknown

Components

Name UniProt ID Details
GDP-mannose 6-dehydrogenase P11759 Details

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
  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

13. Actin, alpha skeletal muscle

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Actin, alpha skeletal muscle P68133 Details

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
  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
  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

14. Beta-lactamase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-lactamase P00811 Details

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
  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

15. Nitric oxide synthase oxygenase

Kind: protein

Organism: Staphylococcus aureus (strain MW2)

Pharmacological action: unknown

Components

Name UniProt ID Details
Nitric oxide synthase oxygenase P0A094 Details

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
  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

16. Lysozyme C

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Lysozyme C P61626 Details

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
  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
  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

17. Septum formation protein Maf

Kind: protein

Organism: Bacillus subtilis (strain 168)

Pharmacological action: unknown

Components

Name UniProt ID Details
Septum formation protein Maf Q02169 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:19