ID: ALA5314358

Max Phase: Preclinical

Molecule Features

Natural Product: No

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:

Molecular Weight (Monoisotopic):

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Dumont B, Joly J, Chapleur Y, Marsura A.  (1994)  New Oligosaccharidic Crown Ethers as Potential Drug-Targetting Vectors: Synthesis & Biological Evaluation,  4  (9): [10.1016/S0960-894X(01)80240-7]

2. Minke WE, Diller DJ, Hol WG, Verlinde CL..  (1999)  The role of waters in docking strategies with incremental flexibility for carbohydrate derivatives: heat-labile enterotoxin, a multivalent test case.,  42  (10): [PMID:10346930] [10.1021/jm980472c]

3. Bernardi A, Carrettoni L, Ciponte AG, Monti D, Sonnino S..  (2000)  Second generation mimics of ganglioside GM1 as artificial receptors for cholera toxin: replacement of the sialic acid moiety.,  10  (19): [PMID:11012028] [10.1016/s0960-894x(00)00428-5]

4. 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]

5. Salameh BA, Leffler H, Nilsson UJ..  (2005)  3-(1,2,3-Triazol-1-yl)-1-thio-galactosides as small, efficient, and hydrolytically stable inhibitors of galectin-3.,  15  (14): [PMID:15963723] [10.1016/j.bmcl.2005.05.084]

6. Tejler J, Leffler H, Nilsson UJ..  (2005)  Synthesis of O-galactosyl aldoximes as potent LacNAc-mimetic galectin-3 inhibitors.,  15  (9): [PMID:15837322] [10.1016/j.bmcl.2005.02.079]

7. Giguère D, Sato S, St-Pierre C, Sirois S, Roy R..  (2006)  Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: role of electrostatic potential at O-3.,  16  (6): [PMID:16403629] [10.1016/j.bmcl.2005.12.010]

8. Chen IJ, Chen HL, Demetriou M..  (2007)  Lateral compartmentalization of T cell receptor versus CD45 by galectin-N-glycan binding and microfilaments coordinate basal and activation signaling.,  282  (48): [PMID:17897956] [10.1074/jbc.m706923200]

9. Giguère D, Bonin MA, Cloutier P, Patnam R, St-Pierre C, Sato S, Roy R..  (2008)  Synthesis of stable and selective inhibitors of human galectins-1 and -3.,  16  (16): [PMID:18674915] [10.1016/j.bmc.2008.06.044]

10. Delaine T, Cumpstey I, Ingrassia L, Le Mercier M, Okechukwu P, Leffler H, Kiss R, Nilsson UJ..  (2008)  Galectin-inhibitory thiodigalactoside ester derivatives have antimigratory effects in cultured lung and prostate cancer cells.,  51  (24): [PMID:19053747] [10.1021/jm801077j]

11. 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]

12. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

13. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

14. 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]

15. Giguère D, André S, Bonin MA, Bellefleur MA, Provencal A, Cloutier P, Pucci B, Roy R, Gabius HJ..  (2011)  Inhibitory potential of chemical substitutions at bioinspired sites of β-D-galactopyranose on neoglycoprotein/cell surface binding of two classes of medically relevant lectins.,  19  (10): [PMID:21524586] [10.1016/j.bmc.2011.03.022]

16. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

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

18. André S, Jarikote DV, Yan D, Vincenz L, Wang GN, Kaltner H, Murphy PV, Gabius HJ..  (2012)  Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons.,  22  (1): [PMID:22142540] [10.1016/j.bmcl.2011.11.010]

19. PubChem BioAssay data set, 

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

21. Marchiori MF, Souto DE, Bortot LO, Pereira JF, Kubota LT, Cummings RD, Dias-Baruffi M, Carvalho I, Campo VL..  (2015)  Synthetic 1,2,3-triazole-linked glycoconjugates bind with high affinity to human galectin-3.,  23  (13): [PMID:25975642] [10.1016/j.bmc.2015.04.044]

22. Kaltner H, Szabó T, Fehér K, André S, Balla S, Manning JC, Szilágyi L, Gabius HJ..  (2017)  Bivalent O-glycoside mimetics with S/disulfide/Se substitutions and aromatic core: Synthesis, molecular modeling and inhibitory activity on biomedically relevant lectins in assays of increasing physiological relevance.,  25  (12): [PMID:28483453] [10.1016/j.bmc.2017.04.011]

23. Unpublished dataset, 

24. Patel B,Kishor C,Houston TA,Shatz-Azoulay H,Zick Y,Vinik Y,Blanchard H.  (2020)  Rational Design and Synthesis of Methyl-β-d-galactomalonyl Phenyl Esters as Potent Galectin-8N Antagonists.,  63  (20.0): [PMID:32809817] [10.1021/acs.jmedchem.0c00602]

25. Hassan M, van Klaveren S, Håkansson M, Diehl C, Kovačič R, Baussière F, Sundin AP, Dernovšek J, Walse B, Zetterberg F, Leffler H, Anderluh M, Tomašič T, Jakopin Ž, Nilsson UJ..  (2021)  Benzimidazole-galactosides bind selectively to the Galectin-8 N-Terminal domain: Structure-based design and optimisation.,  223  [PMID:34225180] [10.1016/j.ejmech.2021.113664]

26. Manning JC, Baldoneschi V, Romero-Hernández LL, Pichler KM, GarcÍa Caballero G, André S, Kutzner TJ, Ludwig AK, Zullo V, Richichi B, Windhager R, Kaltner H, Toegel S, Gabius HJ, Murphy PV, Nativi C..  (2022)  Targeting osteoarthritis-associated galectins and an induced effector class by a ditopic bifunctional reagent: Impact of its glycan part on binding measured in the tissue context.,  75  [PMID:36327696] [10.1016/j.bmc.2022.117068]

27. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(4):

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