ID: ALA469449

Max Phase: Phase

Molecular Formula: C6H12O5

Molecular Weight: 164.16

Molecule Type: Small molecule

Representations

Synonyms (11): (-)-fucose | Deoxygalactose-cerecor | Elfucose | Fucose | Fucose, l- | Fucose-cerecor | L-(-)-fucose | L-fucose | L-galactomethylose | CERC-803 | NSC-1219
Synonyms from Alternative Forms(11):

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

Standard InChI:  InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1

Standard InChI Key:  SHZGCJCMOBCMKK-DHVFOXMCSA-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: 164.16

Molecular Weight (Monoisotopic): 164.0685

AlogP: -2.19

#Rotatable Bonds: 0

Polar Surface Area: 90.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.30

CX Basic pKa:

CX LogP: -1.89

CX LogD: -1.89

Aromatic Rings: 0

Heavy Atoms: 11

QED Weighted: 0.33

Np Likeness Score: 2.62

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. Sufrin JR, Bernacki RJ, Morin MJ, Korytnyk W..  (1980)  Halogenated L-fucose and D-galactose analogues: synthesis and metabolic effects.,  23  (2): [PMID:7359528] [10.1021/jm00176a008]

3. Witczak ZJ, Sun J, Mielguj R.  (1995)  Synthesis of L-fucopyranosyl-4-thiodisaccharides from levoglucosenone and their inhibitory activity on -L-fucosidase,  5  (18): [10.1016/0960-894X(95)00377-6]

4. Dumas DP, Kajimoto T, Liu KK, Wong C, Berkowitz DB, Danieshefsky SJ.  (1992)  Azasugar and glycal inhibitors of -L-fucosidase,  2  (1): [10.1016/S0960-894X(00)80649-6]

5. 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]

6. 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]

7. Levine PM, Carberry TP, Holub JM, Kirshenbaum K.  (2013)  Crafting precise multivalent architectures,  4  (3): [10.1039/C2MD20338C]

8. Johansson EMV, Kadam RU, Rispoli G, Crusz SA, Bartels K, Diggle SP, Camara M, Williams P, Jaeger K, Darbre T, Reymond J.  (2011)  Inhibition of Pseudomonas aeruginosa biofilms with a glycopeptide dendrimer containing D-amino acids,  2  (5): [10.1039/C0MD00270D]

9. Pera NP, Pieters RJ.  (2014)  Towards bacterial adhesion-based therapeutics and detection methods,  5  (8): [10.1039/C3MD00346A]

10. 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]

11. Unpublished dataset, 

12. 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]

13. Taouai M, Chakroun K, Sommer R, Michaud G, Giacalone D, Ben Maaouia MA, Vallin-Butruille A, Mathiron D, Abidi R, Darbre T, Cragg PJ, Mullié C, Reymond JL, O'Toole GA, Benazza M..  (2019)  Glycocluster Tetrahydroxamic Acids Exhibiting Unprecedented Inhibition of Pseudomonas aeruginosa Biofilms.,  62  (17): [PMID:31449405] [10.1021/acs.jmedchem.9b00481]

14. Meiers J,Zahorska E,Röhrig T,Hauck D,Wagner S,Titz A.  (2020)  Directing Drugs to Bugs: Antibiotic-Carbohydrate Conjugates Targeting Biofilm-Associated Lectins of Pseudomonas aeruginosa.,  63  (20): [PMID:32924479] [10.1021/acs.jmedchem.0c00856]

15. Wagner S, Sommer R, Hinsberger S, Lu C, Hartmann RW, Empting M, Titz A..  (2016)  Novel Strategies for the Treatment of Pseudomonas aeruginosa Infections.,  59  (13): [PMID:26804741] [10.1021/acs.jmedchem.5b01698]

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

17. International Nonproprietary Names for Pharmaceutical Substances (INN), 

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• International Nonproprietary Names