Synonym
MPro 13b; MPro13b; MPro-13b;
IUPAC/Chemical Name
tert-butyl (1-((S)-1-(((S)-4-(benzylamino)-3,4-dioxo-1-((S)-2-oxopyrrolidin-3-yl)butan-2-yl)amino)-3-cyclopropyl-1-oxopropan-2-yl)-2-oxo-1,2-dihydropyridin-3-yl)carbamate
InChi Key
NLVRHQFXQFSBQK-XWGVYQGASA-N
InChi Code
InChI=1S/C31H39N5O7/c1-31(2,3)43-30(42)35-22-10-7-15-36(29(22)41)24(16-19-11-12-19)27(39)34-23(17-21-13-14-32-26(21)38)25(37)28(40)33-18-20-8-5-4-6-9-20/h4-10,15,19,21,23-24H,11-14,16-18H2,1-3H3,(H,32,38)(H,33,40)(H,34,39)(H,35,42)/t21-,23-,24-/m0/s1
SMILES Code
CC(OC(NC1=CC=CN([C@@H](CC2CC2)C(N[C@@H](C[C@@H]3CCNC3=O)C(C(NCC4=CC=CC=C4)=O)=O)=O)C1=O)=O)(C)C
Purity
>97% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
SARS-CoV-2-IN-1 is a potent Mpro inhibitor. SARS-CoV-2-IN-1 inhibits the purified recombinant SARS-CoV-2 Mpro, SARS-CoV Mpro and MERS-CoV Mpro with IC50s of 0.67, 0.90 and 0.58 μM, respectively.
In vitro activity:
An attractive drug target among coronaviruses is the main protease (Mpro, also called 3CLpro) because of its essential role in processing the polyproteins that are translated from the viral RNA. On the basis of the unliganded structure, this study developed the lead compound into a potent inhibitor of the SARS-CoV-2 Mpro.
Reference: Science. 2020 Apr 24;368(6489):409-412. https://pubmed.ncbi.nlm.nih.gov/32198291/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
59.4 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
593.68
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Cooper MS, Zhang L, Ibrahim M, Zhang K, Sun X, Röske J, Göhl M, Brönstrup M, Cowell JK, Sauerhering L, Becker S, Vangeel L, Jochmans D, Neyts J, Rox K, Marsh GP, Maple HJ, Hilgenfeld R. Diastereomeric Resolution Yields Highly Potent Inhibitor of SARS-CoV-2 Main Protease. J Med Chem. 2022 Oct 13;65(19):13328-13342. doi: 10.1021/acs.jmedchem.2c01131. Epub 2022 Sep 30. PMID: 36179320; PMCID: PMC9574927.
2. Zhang L, Lin D, Sun X, Curth U, Drosten C, Sauerhering L, Becker S, Rox K, Hilgenfeld R. Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved α-ketoamide inhibitors. Science. 2020 Apr 24;368(6489):409-412. doi: 10.1126/science.abb3405. Epub 2020 Mar 20. PMID: 32198291; PMCID: PMC7164518.
In vitro protocol:
1. Cooper MS, Zhang L, Ibrahim M, Zhang K, Sun X, Röske J, Göhl M, Brönstrup M, Cowell JK, Sauerhering L, Becker S, Vangeel L, Jochmans D, Neyts J, Rox K, Marsh GP, Maple HJ, Hilgenfeld R. Diastereomeric Resolution Yields Highly Potent Inhibitor of SARS-CoV-2 Main Protease. J Med Chem. 2022 Oct 13;65(19):13328-13342. doi: 10.1021/acs.jmedchem.2c01131. Epub 2022 Sep 30. PMID: 36179320; PMCID: PMC9574927.
2. Zhang L, Lin D, Sun X, Curth U, Drosten C, Sauerhering L, Becker S, Rox K, Hilgenfeld R. Crystal structure of SARS-CoV-2 main protease provides a basis for design of improved α-ketoamide inhibitors. Science. 2020 Apr 24;368(6489):409-412. doi: 10.1126/science.abb3405. Epub 2020 Mar 20. PMID: 32198291; PMCID: PMC7164518.
1: Pitsillou E, Liang J, Karagiannis C, Ververis K, Darmawan KK, Ng K, Hung A, Karagiannis TC. Interaction of small molecules with the SARS-CoV-2 main protease in silico and in vitro validation of potential lead compounds using an enzyme- linked immunosorbent assay. Comput Biol Chem. 2020 Dec;89:107408. doi: 10.1016/j.compbiolchem.2020.107408. Epub 2020 Oct 23. PMID: 33137690; PMCID: PMC7583591.
2: Han Y, Wang Z, Ren J, Wei Z, Li J. Potential inhibitors for the novel coronavirus (SARS-CoV-2). Brief Bioinform. 2020 Sep 18:bbaa209. doi: 10.1093/bib/bbaa209. Epub ahead of print. PMID: 32942296; PMCID: PMC7543260.
3: Liang J, Karagiannis C, Pitsillou E, Darmawan KK, Ng K, Hung A, Karagiannis TC. Site mapping and small molecule blind docking reveal a possible target site on the SARS-CoV-2 main protease dimer interface. Comput Biol Chem. 2020 Dec;89:107372. doi: 10.1016/j.compbiolchem.2020.107372. Epub 2020 Sep 5. PMID: 32911432.
4: Poater A. Michael Acceptors Tuned by the Pivotal Aromaticity of Histidine to Block COVID-19 Activity. J Phys Chem Lett. 2020 Aug 6;11(15):6262-6265. doi: 10.1021/acs.jpclett.0c01828. Epub 2020 Jul 22. PMID: 32658489; PMCID: PMC7376971.
5: Ngo ST, Quynh Anh Pham N, Thi Le L, Pham DH, Vu VV. Computational Determination of Potential Inhibitors of SARS-CoV-2 Main Protease. J Chem Inf Model. 2020 Jun 28:acs.jcim.0c00491. doi: 10.1021/acs.jcim.0c00491. Epub ahead of print. PMID: 32530282; PMCID: PMC7323056.
6: Liang J, Pitsillou E, Karagiannis C, Darmawan KK, Ng K, Hung A, Karagiannis TC. Interaction of the prototypical α-ketoamide inhibitor with the SARS-CoV-2 main protease active site in silico: Molecular dynamic simulations highlight the stability of the ligand-protein complex. Comput Biol Chem. 2020 May 28;87:107292. doi: 10.1016/j.compbiolchem.2020.107292. Epub ahead of print. PMID: 32485652; PMCID: PMC7253975.
7: Mittal L, Kumari A, Srivastava M, Singh M, Asthana S. Identification of potential molecules against COVID-19 main protease through structure-guided virtual screening approach. J Biomol Struct Dyn. 2020 May 20:1-19. doi: 10.1080/07391102.2020.1768151. Epub ahead of print. PMID: 32396769; PMCID: PMC7256355.
