PASS Predication, Antiviral, in vitro Antimicrobial, and ADMET Studies of Rhamnopyranoside Esters Methyl α-L-rhamnopyranoside; Sugar esters (SEs); PASS predication; Antiviral; Antimicrobial activities; ADMET

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Mohammed Mahbubul Matin Md. HO Roshid, MBBS, MD Sreebash C Bhattacharjee, Dr Abul KMS Azad, Dr


Sugar derived esters (SEs) with potential antimicrobial activity were found to be a better choice to solve the multidrug resistant (MDR) pathogens due to improved antimicrobial efficacy, biodegradability, non-toxic, and non-allergic properties. In this context, a series of benzyl a-L-rhamnopyranoside esters with different chain length (C2-C18) were employed for PASS predication, antiviral, and in vitro antimicrobial activity test. The in vitro antimicrobial tests against four bacterial, and four fungal pathogens along with PASS predication indicated that these sugar esters acted as better antifungals as compared to antibacterial functionality. The study revealed that the incorporation of octanoyl (C8) and lauroyl (C12) group(s) at C-3 position of rhamnopyranoside possessed promising antimicrobial, and anti-carcinogenic potentiality with good pharmacokinetic (pkCSM), and drug likeness properties. Also, attachment of multiple ester groups enhanced various drug likeness, and medicinal chemistry friendliness conditions. Overall, the present findings might be useful for the development of rhamnopyranoside based novel MDR antimicrobial drugs.

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MATIN, Mohammed Mahbubul et al. PASS Predication, Antiviral, in vitro Antimicrobial, and ADMET Studies of Rhamnopyranoside Esters. Medical Research Archives, [S.l.], v. 8, n. 7, july 2020. ISSN 2375-1924. Available at: <>. Date accessed: 04 aug. 2020. doi:
Research Articles


1. Rai J, Randhawa GK, Kaur M. Recent advances in antibacterial drugs. Int. J. Appl. Basic Med. Res. 2013;3:3‐10.
2. Kim HJ, Kim MK, Lee MJ, et al. Post-PKS tailoring steps of a disaccharide-containing polyene NPP in Pseudonocardia autotrophica. PLoS One 2015;10(4):e0123270. doi:
3. Kim HJ, Kang SH, Choi SS, Kim ES. Redesign of antifungal polyene glycosylation: engineered biosynthesis of disaccharide-modified NPP. Appl. Microbiol. Biotechnol. 2017;101: 5131-5137.
4. Pöhnlein M, Slomka C, Kukharenko O, et al. Enzymatic synthesis of amino sugar fatty acid esters. Eur. J. Lipid Sci. Technol. 2014;116:423-428.
5. Matin MM, Bhattacharjee SC, Chakraborty P, Alam MS. Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters. Carbohydr. Res. 2019;485:107812. doi:
6. Matin MM, Bhuiyan MMH, Kabir E, et al. Synthesis, characterization, ADMET, PASS predication, and antimicrobial study of 6-O-lauroylmannopyranosides. J. Mol. Struct. 2019;1195:189-197. doi:
7. Matin MM, Iqbal MZ. (2008). Synthesis and antimicrobial evaluation of some methyl 4-O-decanoyl-α-L-rhamnopyranoside derivatives. Proc. Bangladesh Chem. Congress, 2008;254-263. doi:
8. Mihoub M, Pichette A, Sylla B, et al. Bidesmosidic betulin saponin bearing L-rhamnopyranoside moieties induces apoptosis and inhibition of lung cancer cells growth in vitro and in vivo. PLoS ONE 2018;13(3):e0193386. doi:
9. Matin MM, Nath AR, Saad O, et al. Synthesis, PASS-predication and in vitro antimicrobial activity of benzyl 4-O-benzoyl-α-L-rhamnopyranoside derivatives. Int. J. Mol. Sci., 2016;17:1442. doi:
10. Kabir AKMS, Matin MM, Hossain A, Sattar MA. Synthesis and antimicrobial activities of some rhamnopyranoside derivatives. J. Bangladesh Chem. Soc. 2003;16(2):85-93.
11. Kim SR, Kim YC. Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. Phytochem. 2000;54:503-509.
12. Elmaidomy AH, Mohammed R, Owis AI, et al. Triple-negative breast cancer suppressive activities, antioxidants and pharmacophore model of new acylated rhamnopyranoses from Premna odorata. RSC Adv. 2020;10:10584.
13. Matin MM. Synthesis and antimicrobial study of some methyl 4-O-palmitoyl-α-L-rhamnopyranoside derivatives. Orbital: Electron. J. Chem. 2014;6(1):20-28. doi:
14. Matin MM, Ibrahim M. Synthesis of some methyl 4-O-octnoyl-α-L-rhamnopyranoside derivatives. J. Appl. Sci. Res. 2010;6(10):1527-1532.
15. Matin MM, Bhuiyan MMH, Hossain MM, Roshid MHO. Synthesis and comparative antibacterial studies of some benzylidene monosaccharide benzoates. J. Turkish Chem. Soc., Sect. A: Chem. 2015;2(4):12-21.
16. Kabir AKMS, Matin MM, Islam KR, Manchur MA. Synthesis and antimicrobial activities of some monosaccharide derivatives. Chittagong Univ. J. Sci. 1999;23(2):01-08.
17. Kabir AKMS, Matin MM. Regioselective acylation of a derivative of L-rhamnose using the dibutyltin oxide method. J. Bangladesh Chem. Soc. 1994;7(1):73-79.
18. Kabir AKMS, Matin MM. Regioselective monoacylation of a derivative of L-rhamnose. J. Bangladesh Acad. Sci. 1997;21(1):83-88.
19. Qureshi A, Kaur G, Kumar M. AVCpred: An integrated web server for prediction and design of antiviral compounds. Chem. Biol. Drug Des. 2016. doi:
20. Matin MM, Bhuiyan MMH, Debnath DC, Manchur MA. Synthesis and comparative antimicrobial studies of some acylated D-glucofuranose and D-glucopyranose derivatives. Int. J. Biosci. 2013;3(8):279-287. doi:
21. Matin MM, Ibrahim M. Synthesis of 2,3-di-O-substituted derivatives of methyl 4-O-acetyl-α-L-rhamnopyranoside. Chittagong Univ. J. Sci. 2006;30(2):67-76.
22. Matin MM, Ibrahim M, Rahman MS. Antimicrobial evaluation of methyl 4-O-acetyl-α-L-rhamnopyranoside derivatives. Chittagong Univ. J. Biol. Sci. 2008;3(1&2):33-43.
23. Kabir AKMS, Matin MM, Hossain A, Rahman MS. Synthesis and antimicrobial activities of some acylated derivatives of L-rhamnose. Chittagong Univ. J. Sci. 2002;26(1&2):35-44.
24. Kabir AKMS, Matin MM, Rahman MS. Antimicrobial activities of some rhamnoside derivatives. Chittagong Univ. J. Sci. 2000;24(1):129-135.
25. Pires DEV, Blundell TL, Ascher DB. pkCSM: predicting small-molecule pharmacokinetic properties using graph-based signatures. J. Med. Chem. 2015;58(9):4066–4072.
26. Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep. 2017;7:42717. doi:
27. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997;23:3-25.

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