6-Hydroxymethyl-tetrahydro-pyran-2,3,4,5-tetraol

ID: ALA1222250

Cas Number: 54-17-1

PubChem CID: 5793

Product Number: R589414, Order Now?

Max Phase: Approved

Molecular Formula: C6H12O6

Molecular Weight: 180.16

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Anhydrous dextrose | Anhydrous glucose | D-glucose, anhydrous | Dextrose | Dextrose anhydrous | Dextrose solution | Dextrose, anhydrous | Dextrose, unspecified | Dextrose, unspecified form | Glucose anhydrous | Glucose injection | Glucose, alpha-d- | Glucose, anhydrous | Glucose, liquid | Glucose, unspecified form | Glucosum, anhydrous | Grape sugar | Liquid glucose | NSC-406891 | D-Glc|D-Glucopyranose|D-Glucopyranoside|D-Glucose|Glc|Glucopyranose|Glucopyranoside|Glucose|dextrose|2280-44-6|GrapeShow More⌵

Trade Names(8): Capd | Clintec | Dextro energy | Dextrogel | Gambrosol | Gsf-syrup | Rapilose | Yourgluco

Canonical SMILES:  OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O

Standard 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

Standard InChI Key:  WQZGKKKJIJFFOK-GASJEMHNSA-N

Molfile:  

     RDKit          2D

 12 12  0  0  0  0  0  0  0  0999 V2000
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  1
  9 11  1  0
  3 11  1  0
 11 12  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1222250

   rel-(3R,4S,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 180.16

Molecular Weight (Monoisotopic): 180.0634

AlogP: -3.22

#Rotatable Bonds: 1

Polar Surface Area: 110.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.30

CX Basic pKa: ┄

CX LogP: -2.93

CX LogD: -2.93

Aromatic Rings: ┄

Heavy Atoms: 12

QED Weighted: 0.29

Np Likeness Score: 2.63

References

1. de Robertis L, Lancelon-Pin C, Driguez H, Attioui F, Bonaly R, Alain M.  (1994)  Synthesis of new oligosaccharidyl-thio--cyclodextrins (CDS): a novel family of potent drug-targetting vectors.,  4  (9): [10.1016/S0960-894X(01)80241-9]

2. Anderson RA, Oswald C, Zaneveld LJ..  (1981)  Inhibition of human acrosin by monosaccharides and related compounds: structure-activity relationships.,  24  (11): [PMID:7031247] [10.1021/jm00143a005]

3. Pastor M, Cruciani G, Clementi S..  (1997)  Smart region definition: a new way to improve the predictive ability and interpretability of three-dimensional quantitative structure-activity relationships.,  40  (10): [PMID:9154968] [10.1021/jm9608016]

4. Andrews PR, Craik DJ, Martin JL..  (1984)  Functional group contributions to drug-receptor interactions.,  27  (12): [PMID:6094812] [10.1021/jm00378a021]

5. Hadwiger P, Mayr P, Tauss A, Stütz AE, Nidetzky B..  (1999)  Binding and catalysis by yeast aldose reductase: a substrate-analog approach with new aldose derivatives.,  9  (12): [PMID:10397501] [10.1016/s0960-894x(99)00255-3]

6. Danelian E, Karlén A, Karlsson R, Winiwarter S, Hansson A, Löfâs S, Lennernäs H, Hämäläinen MD..  (2000)  SPR biosensor studies of the direct interaction between 27 drugs and a liposome surface: correlation with fraction absorbed in humans.,  43  (11): [PMID:10841786] [10.1021/jm991156g]

7. Venkatarangan P, Hopfinger AJ..  (1999)  Prediction of ligand-receptor binding thermodynamics by free energy force field three-dimensional quantitative structure-activity relationship analysis: applications to a set of glucose analogue inhibitors of glycogen phosphorylase.,  42  (12): [PMID:10377222] [10.1021/jm980515p]

8. Venkatarangan P, Hopfinger AJ..  (1999)  Prediction of ligand-receptor binding thermodynamics by free energy force field three-dimensional quantitative structure-activity relationship analysis: applications to a set of glucose analogue inhibitors of glycogen phosphorylase.,  42  (12): [PMID:10377222] [10.1021/jm980515p]

9. Cruciani G, Watson KA..  (1994)  Comparative molecular field analysis using GRID force-field and GOLPE variable selection methods in a study of inhibitors of glycogen phosphorylase b.,  37  (16): [PMID:8057302] [10.1021/jm00042a012]

10. Ishchenko AV, Shakhnovich EI..  (2002)  SMall Molecule Growth 2001 (SMoG2001): an improved knowledge-based scoring function for protein-ligand interactions.,  45  (13): [PMID:12061879] [10.1021/jm0105833]

11. Somsák L, Kovács L, Tóth M, Osz E, Szilágyi L, Györgydeák Z, Dinya Z, Docsa T, Tóth B, Gergely P..  (2001)  Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides.,  44  (17): [PMID:11495595] [10.1021/jm010892t]

12. Pan D, Liu J, Senese C, Hopfinger AJ, Tseng Y..  (2004)  Characterization of a ligand-receptor binding event using receptor-dependent four-dimensional quantitative structure-activity relationship analysis.,  47  (12): [PMID:15163189] [10.1021/jm030586a]

13. Pastor M, Cruciani G, McLay I, Pickett S, Clementi S..  (2000)  GRid-INdependent descriptors (GRIND): a novel class of alignment-independent three-dimensional molecular descriptors.,  43  (17): [PMID:10966742] [10.1021/jm000941m]

14. Zamora I, Oprea T, Cruciani G, Pastor M, Ungell AL..  (2003)  Surface descriptors for protein-ligand affinity prediction.,  46  (1): [PMID:12502357] [10.1021/jm011051p]

15. Pastor M, Cruciani G, Watson KA..  (1997)  A strategy for the incorporation of water molecules present in a ligand binding site into a three-dimensional quantitative structure--activity relationship analysis.,  40  (25): [PMID:9406599] [10.1021/jm970273d]

16. Gohlke H, Klebe G..  (2002)  DrugScore meets CoMFA: adaptation of fields for molecular comparison (AFMoC) or how to tailor knowledge-based pair-potentials to a particular protein.,  45  (19): [PMID:12213058] [10.1021/jm020808p]

17. Gohlke H, Klebe G..  (2002)  DrugScore meets CoMFA: adaptation of fields for molecular comparison (AFMoC) or how to tailor knowledge-based pair-potentials to a particular protein.,  45  (19): [PMID:12213058] [10.1021/jm020808p]

18. Dumas DP, Ichikawa Y, Wong C, Lowe JB, Nair RP.  (1991)  Enzymatic synthesis of sialyl Lex and derivatives based on a recombinant fucosyltransferase,  1  (8): [10.1016/S0960-894X(00)80270-X]

19. So SS, Karplus M..  (1997)  Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 2. Applications.,  40  (26): [PMID:9435905] [10.1021/jm970488n]

20. Winiwarter S, Bonham NM, Ax F, Hallberg A, Lennernäs H, Karlén A..  (1998)  Correlation of human jejunal permeability (in vivo) of drugs with experimentally and theoretically derived parameters. A multivariate data analysis approach.,  41  (25): [PMID:9836611] [10.1021/jm9810102]

21. McMaster PD, Byrnes EW, Block AJ, Tenthorey PA..  (1981)  New antiarrhythmic agents. 5. alpha-Aminoaceto-2,6-xylidides with functionalized amide alkyl substituents.,  24  (1): [PMID:7205876] [10.1021/jm00133a012]

22. Bhat N, Joe A, PereiraPerrin M, Ward HD..  (2007)  Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.,  282  (48): [PMID:17905738] [10.1074/jbc.m706950200]

23. Gynther M, Ropponen J, Laine K, Leppänen J, Haapakoski P, Peura L, Järvinen T, Rautio J..  (2009)  Glucose promoiety enables glucose transporter mediated brain uptake of ketoprofen and indomethacin prodrugs in rats.,  52  (10): [PMID:19402664] [10.1021/jm8015409]

24. Saito K, Matsumoto M, Sekine T, Murakoshi I, Morisaki N, Iwasaki S.  (1989)  Inhibitory Substances from Myriophyllum brasiliense on Growth of Blue-Green Algae,  52  (6): [10.1021/np50066a004]

25. Su BN, Pawlus AD, Jung HA, Keller WJ, McLaughlin JL, Kinghorn AD..  (2005)  Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.,  68  (4): [PMID:15844957] [10.1021/np0495985]

26. Gruzman A, Shamni O, Ben Yakir M, Sandovski D, Elgart A, Alpert E, Cohen G, Hoffman A, Katzhendler Y, Cerasi E, Sasson S..  (2008)  Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase alpha.,  51  (24): [PMID:19049348] [10.1021/jm8008713]

27. Avdeef A, Tam KY..  (2010)  How well can the Caco-2/Madin-Darby canine kidney models predict effective human jejunal permeability?,  53  (9): [PMID:20373811] [10.1021/jm901846t]

28. Lairson LL, Watts AG, Wakarchuk WW, Withers SG..  (2006)  Using substrate engineering to harness enzymatic promiscuity and expand biological catalysis.,  2  (12): [PMID:17057723] [10.1038/nchembio828]

29. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

30. Unpublished dataset, 

31. PubChem BioAssay data set, 

32. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

33. Verspohl EJ, Bozdag-Dundar O, Kaup RM, Bauer K, Ertan R.  (2009)  Insulinotropic activity of chromonyl-2,4-thiazolidinediones,  18  (8): [10.1007/s00044-008-9158-4]

34. Yildiz I, Bozdag-Dundar O.  (2010)  Three-dimensional common-feature hypotheses for hypoglycemic flavonyl-2,4-thiazolidinedione derivatives,  19  (3): [10.1007/s00044-009-9185-9]

35. PubChem BioAssay data set, 

36. PubChem BioAssay data set, 

37. Parmenopoulou V, Kantsadi AL, Tsirkone VG, Chatzileontiadou DS, Manta S, Zographos SE, Molfeta C, Archontis G, Agius L, Hayes JM, Leonidas DD, Komiotis D..  (2014)  Structure based inhibitor design targeting glycogen phosphorylase B. Virtual screening, synthesis, biochemical and biological assessment of novel N-acyl-β-d-glucopyranosylamines.,  22  (17): [PMID:25092521] [10.1016/j.bmc.2014.06.058]

38. Kaffy J, Brinet D, Soulier JL, Khemtémourian L, Lequin O, Taverna M, Crousse B, Ongeri S..  (2014)  Structure-activity relationships of sugar-based peptidomimetics as modulators of amyloid β-peptide early oligomerization and fibrillization.,  86  [PMID:25238173] [10.1016/j.ejmech.2014.09.031]

39. Gibbs AC..  (2014)  Elements and modulation of functional dynamics.,  57  (19): [PMID:24913411] [10.1021/jm500325k]

40. Farrell TL, Poquet L, Dew TP, Barber S, Williamson G..  (2012)  Predicting phenolic acid absorption in Caco-2 cells: a theoretical permeability model and mechanistic study.,  40  (2): [PMID:22096083] [10.1124/dmd.111.041665]

41. WHO Anatomical Therapeutic Chemical Classification, 

42. British National Formulary (72nd edition), 

43. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

44. Perrone MG, Vitale P, Ferorelli S, Boccarelli A, Coluccia M, Pannunzio A, Campanella F, Di Mauro G, Bonaccorso C, Fortuna CG, Scilimati A..  (2017)  Effect of mofezolac-galactose distance in conjugates targeting cyclooxygenase (COX)-1 and CNS GLUT-1 carrier.,  141  [PMID:29032033] [10.1016/j.ejmech.2017.09.066]

45. Nkosana NK, Czyzyk DJ, Siegel ZS, Cote JM, Taylor EA..  (2018)  Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A.,  28  (4): [PMID:29398539] [10.1016/j.bmcl.2018.01.040]

46. Itoh T, Tamura K, Ueda H, Tanaka T, Sato K, Kuroda R, Aoki S..  (2018)  Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT).,  26  (22): [PMID:30420329] [10.1016/j.bmc.2018.10.041]

47. Unpublished dataset, 

48. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

49.  (2014)  Fibcd1 for the prevention and treatment of diseases, 

50. Meegalla SK, Huang H, Illig CR, Parks DJ, Chen J, Lee YK, Wilson KJ, Patel SK, Cheung WS, Lu T, Kirchner T, Askari HB, Geisler J, Patch RJ, Gibbs AC, Rady B, Connelly M, Player MR..  (2016)  Discovery of novel potent imidazo[1,2-b]pyridazine PDE10a inhibitors.,  26  (17): [PMID:27491708] [10.1016/j.bmcl.2016.07.054]

51. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

52. Simone MI, Wood A, Campkin D, Kiefel MJ, Houston TA..  (2022)  Recent results from non-basic glycosidase inhibitors: How structural diversity can inform general strategies for improving inhibition potency.,  235  [PMID:35367706] [10.1016/j.ejmech.2022.114282]

53. Philipp Leippe.  (2022)  Flow cytometry transport assay for SLC2A1 using HEK293 JumpIN TRex SLC2A1 WT-OE cells,  [10.5281/zenodo.7360676]

54. Philipp Leippe.  (2022)  Flow cytometry transport assay for SLC2A2 using HEK293 JumpIN TRex SLC2A2 WT-OE cells,  [10.5281/zenodo.7360664]

55. Philipp Leippe.  (2022)  Flow cytometry transport assay for SLC2A4 using HEK293 JumpIN TRex SLC2A4 WT-OE cells,  [10.5281/zenodo.7360638]

56. Philipp Leippe.  (2022)  Flow cytometry transport assay for SLC2A3 using HEK293 JumpIN TRex SLC2A3 WT-OE cells,  [10.5281/zenodo.7360656]

Source

Source(11):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• Patent Bioactivity Data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• RESOLUTE - Research Empowerment on Solute Carriers