D-glucose   Click here for help

GtoPdb Ligand ID: 4536

Compound class: Metabolite
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 5
Rotatable bonds 1
Topological polar surface area 110.38
Molecular weight 180.06
XLogP -1.7
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OCC1OC(O)C(C(C1O)O)O
Isomeric SMILES OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1
InChI Key WQZGKKKJIJFFOK-GASJEMHNSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Burant CF, Takeda J, Brot-Laroche E, Bell GI, Davidson NO. (1992)
Fructose transporter in human spermatozoa and small intestine is GLUT5.
J Biol Chem, 267 (21): 14523-6. [PMID:1634504]
2. Cheeseman C. (2008)
GLUT7: a new intestinal facilitated hexose transporter.
Am J Physiol Endocrinol Metab, 295 (2): E238-41. [PMID:18477702]
3. Coady MJ, Wallendorff B, Gagnon DG, Lapointe JY. (2002)
Identification of a novel Na+/myo-inositol cotransporter.
J Biol Chem, 277 (38): 35219-24. [PMID:12133831]
4. Doege H, Bocianski A, Scheepers A, Axer H, Eckel J, Joost HG, Schürmann A. (2001)
Characterization of human glucose transporter (GLUT) 11 (encoded by SLC2A11), a novel sugar-transport facilitator specifically expressed in heart and skeletal muscle.
Biochem J, 359 (Pt 2): 443-9. [PMID:11583593]
5. Hager K, Hazama A, Kwon HM, Loo DD, Handler JS, Wright EM. (1995)
Kinetics and specificity of the renal Na+/myo-inositol cotransporter expressed in Xenopus oocytes.
J Membr Biol, 143 (2): 103-13. [PMID:7537337]
6. Ibberson M, Uldry M, Thorens B. (2000)
GLUTX1, a novel mammalian glucose transporter expressed in the central nervous system and insulin-sensitive tissues.
J Biol Chem, 275 (7): 4607-12. [PMID:10671487]
7. Lee YC, Huang HY, Chang CJ, Cheng CH, Chen YT. (2010)
Mitochondrial GLUT10 facilitates dehydroascorbic acid import and protects cells against oxidative stress: mechanistic insight into arterial tortuosity syndrome.
Hum Mol Genet, 19 (19): 3721-33. [PMID:20639396]
8. Rogers S, Chandler JD, Clarke AL, Petrou S, Best JD. (2003)
Glucose transporter GLUT12-functional characterization in Xenopus laevis oocytes.
Biochem Biophys Res Commun, 308 (3): 422-6. [PMID:12914765]
9. Uldry M, Ibberson M, Hosokawa M, Thorens B. (2002)
GLUT2 is a high affinity glucosamine transporter.
FEBS Lett, 524 (1-3): 199-203. [PMID:12135767]
10. Voss AA, Díez-Sampedro A, Hirayama BA, Loo DD, Wright EM. (2007)
Imino sugars are potent agonists of the human glucose sensor SGLT3.
Mol Pharmacol, 71 (2): 628-34. [PMID:17110502]