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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
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
  • C-glycosyl compound
  • Oxane
  • Oxolane
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
PropertyValueProbability
Human Intestinal Absorption-0.8682
Blood Brain Barrier+0.7245
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.6386
P-glycoprotein inhibitor INon-inhibitor0.8721
P-glycoprotein inhibitor IINon-inhibitor0.9402
Renal organic cation transporterNon-inhibitor0.8146
CYP450 2C9 substrateNon-substrate0.8747
CYP450 2D6 substrateNon-substrate0.8561
CYP450 3A4 substrateNon-substrate0.6536
CYP450 1A2 substrateNon-inhibitor0.9425
CYP450 2C9 substrateNon-inhibitor0.9377
CYP450 2D6 substrateNon-inhibitor0.9395
CYP450 2C19 substrateNon-inhibitor0.8821
CYP450 3A4 substrateNon-inhibitor0.9716
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9258
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9565
BiodegradationNot ready biodegradable0.7256
Rat acute toxicity1.0936 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9633
hERG inhibition (predictor II)Non-inhibitor0.883
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 Solubility824.0 mg/mLALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. 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

2. 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

3. 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

4. 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

5. 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

6. 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

7. Beta-glucosidase

Kind: protein

Organism: Streptomyces sp.

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-glucosidase Q59976 Details

8. Amylosucrase

Kind: protein

Organism: Neisseria polysaccharea

Pharmacological action: unknown

Components

Name UniProt ID Details
Amylosucrase Q9ZEU2 Details

9. Beta-lactamase

Kind: protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Beta-lactamase Q9L5C8 Details

10. Beta-lactamase CTX-M

Kind: protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

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

11. 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

12. Copper transport protein ATOX1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Copper transport protein ATOX1 O00244 Details

13. 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

14. Orange carotenoid-binding protein

Kind: protein

Organism: Arthrospira maxima

Pharmacological action: unknown

Components

Name UniProt ID Details
Orange carotenoid-binding protein P83689 Details

15. Sucrose porin

Kind: protein

Organism: Salmonella typhimurium

Pharmacological action: unknown

Components

Name UniProt ID Details
Sucrose porin P22340 Details

16. Levansucrase

Kind: protein

Organism: Bacillus subtilis (strain 168)

Pharmacological action: unknown

Components

Name UniProt ID Details
Levansucrase P05655 Details

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