ID: ALA469448

Max Phase: Phase

Molecular Formula: C6H12O6

Molecular Weight: 180.16

Molecule Type: Small molecule

Representations

Synonyms (4): Carubinose | D-mannose | Seminose | NSC-26247
Synonyms from Alternative Forms(4):

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-QTVWNMPRSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

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: 0

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.30

CX Basic pKa:

CX LogP: -2.93

CX LogD: -2.93

Aromatic Rings: 0

Heavy Atoms: 12

QED Weighted: 0.29

Np Likeness Score: 2.63

References

1. 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]

2. Winkler DA, Holan G..  (1989)  Design of potential anti-HIV agents. 1. Mannosidase inhibitors.,  32  (9): [PMID:2504921] [10.1021/jm00129a011]

3. Pei Z, Aastrup T, Anderson H, Ramström O..  (2005)  Redox-responsive and calcium-dependent switching of glycosyldisulfide interactions with Concanavalin A.,  15  (11): [PMID:15878660] [10.1016/j.bmcl.2005.04.024]

4. 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]

5. 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]

6. Poláková M, Šesták S, Lattová E, Petruš L, Mucha J, Tvaroška I, Kóňa J..  (2011)  α-D-mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II.,  46  (3): [PMID:21295890] [10.1016/j.ejmech.2011.01.012]

7. Euzen R, Reymond JL..  (2011)  Synthesis of glycopeptide dendrimers, dimerization and affinity for Concanavalin A.,  19  (9): [PMID:21481594] [10.1016/j.bmc.2011.03.047]

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. Scharenberg M, Schwardt O, Rabbani S, Ernst B..  (2012)  Target Selectivity of FimH Antagonists.,  55  (22): [PMID:23088608] [10.1021/jm3010338]

11. Unpublished dataset, 

12. Unpublished dataset, 

13. Unpublished dataset, 

14. Unpublished dataset, 

15. Unpublished dataset, 

16. Tomašić T, Hajšek D, Švajger U, Luzar J, Obermajer N, Petit-Haertlein I, Fieschi F, Anderluh M..  (2014)  Monovalent mannose-based DC-SIGN antagonists: targeting the hydrophobic groove of the receptor.,  75  [PMID:24556146] [10.1016/j.ejmech.2014.01.047]

17. Tomasic T, Rabbani S, Gobec M, Rascan IM, Podlipnik C, Ernst B, Anderluh M.  (2014)  Branched -d-mannopyranosides: a new class of potent FimH antagonists,  5  (8): [10.1039/C4MD00093E]

18. Beshr G, Sommer R, Hauck D, Siebert DCB, Hofmann A, Imberty A, Titz A.  (2016)  Development of a competitive binding assay for the Burkholderia cenocepacia lectin BC2L-A and structure activity relationship of natural and synthetic inhibitors,  7  (3): [10.1039/C5MD00557D]

19. Bosco M, Massarweh A, Iatmanen-Harbi S, Bouhss A, Chantret I, Busca P, Moore SE, Gravier-Pelletier C..  (2017)  Synthesis and biological evaluation of chemical tools for the study of Dolichol Linked Oligosaccharide Diphosphatase (DLODP).,  125  [PMID:27769035] [10.1016/j.ejmech.2016.10.013]

20. Unpublished dataset, 

21. D'Ambrosio EA, Drake WR, Mashayekh S, Ukaegbu OI, Brown AR, Grimes CL..  (2019)  Modulation of the NOD-like receptors NOD1 and NOD2: A chemist's perspective.,  29  (10): [PMID:30890292] [10.1016/j.bmcl.2019.03.010]

22. Sommer R, Rox K, Wagner S, Hauck D, Henrikus SS, Newsad S, Arnold T, Ryckmans T, Brönstrup M, Imberty A, Varrot A, Hartmann RW, Titz A..  (2019)  Anti-biofilm Agents against Pseudomonas aeruginosa: A Structure-Activity Relationship Study of C-Glycosidic LecB Inhibitors.,  62  (20): [PMID:31553873] [10.1021/acs.jmedchem.9b01120]

23.  (2014)  Fibcd1 for the prevention and treatment of diseases, 

Source

Source(5):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Gene Expression Atlas Compounds
• Patent Bioactivity Data