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MedKoo Cat#: 555785 | Name: ML188
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

ML188 is a Potent Noncovalent Small Molecule Inhibitor of the Severe Acute Respiratory Syndrome Coronavirus (SARS-CoV) 3CL Protease. The X-ray structure of SARS-CoV 3CLpro bound with ML188 was instrumental in guiding subsequent rounds of chemistry optimization. ML188 provides an excellent starting point for the further design and refinement of 3CLpro inhibitors that act by a noncovalent mechanism of action.

Chemical Structure

ML188
ML188
CAS#1417700-13-0 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 555785

Name: ML188

CAS#: 1417700-13-0 (R-isomer)

Chemical Formula: C26H31N3O3

Exact Mass: 433.2365

Molecular Weight: 433.55

Elemental Analysis: C, 72.03; H, 7.21; N, 9.69; O, 11.07

Price and Availability

Size Price Availability Quantity
100mg USD 950.00 2 Weeks
200mg USD 1,650.00 2 Weeks
500mg USD 3,250.00 2 Weeks
1g USD 4,950.00 2 Weeks
2g USD 7,950.00 2 Weeks
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Related CAS #
1417699-67-2 (racemic) 1417700-12-9 (S-isomer) 1417700-13-0 (R-isomer)
Synonym
ML188; ML-188; ML 188;
IUPAC/Chemical Name
N-[(1R)-2-(tert-Butylamino)-2-oxo-1-pyridin-3-ylethyl]-N-(4-tert-butylphenyl)furan-2-carboxamide
InChi Key
JXGIYKRRPGCLFV-JOCHJYFZSA-N
InChi Code
InChI=1S/C26H31N3O3/c1-25(2,3)19-11-13-20(14-12-19)29(24(31)21-10-8-16-32-21)22(18-9-7-15-27-17-18)23(30)28-26(4,5)6/h7-17,22H,1-6H3,(H,28,30)/t22-/m1/s1
SMILES Code
O=C(C1=CC=CO1)N([C@H](C2=CC=CN=C2)C(NC(C)(C)C)=O)C3=CC=C(C(C)(C)C)C=C3
Appearance
Solid powder
Purity
>98% (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
>3 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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
ML188, a first in class probe, is a selective non-covalent SARS-CoV 3CLpro inhibitor with an IC50 of 1.5 μM.
In vitro activity:
A high-throughput screen of the NIH molecular libraries sample collection and subsequent optimization of a lead dipeptide-like series of severe acute respiratory syndrome (SARS) main protease (3CLpro) inhibitors led to the identification of probe compound ML188 (16-(R), (R)-N-(4-(tert-butyl)phenyl)-N-(2-(tert-butylamino)-2-oxo-1-(pyridin-3-yl)ethyl)furan-2-carboxamide, Pubchem CID: 46897844). Unlike the majority of reported coronavirus 3CLpro inhibitors that act via covalent modification of the enzyme, 16-(R) is a noncovalent SARS-CoV 3CLpro inhibitor with moderate MW and good enzyme and antiviral inhibitory activity. 16-(R) provides an excellent starting point for the further design and refinement of 3CLpro inhibitors that act by a noncovalent mechanism of action. Reference: J Med Chem. 2013 Jan 24;56(2):534-46. https://pubmed.ncbi.nlm.nih.gov/23231439/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 168.5 388.65
Ethanol 87.0 200.67
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 433.55 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.

Recalculate based on batch purity %
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. Lockbaum GJ, Reyes AC, Lee JM, Tilvawala R, Nalivaika EA, Ali A, Kurt Yilmaz N, Thompson PR, Schiffer CA. Crystal Structure of SARS-CoV-2 Main Protease in Complex with the Non-Covalent Inhibitor ML188. Viruses. 2021 Jan 25;13(2):174. doi: 10.3390/v13020174. PMID: 33503819; PMCID: PMC7911568. 2. Jacobs J, Grum-Tokars V, Zhou Y, Turlington M, Saldanha SA, Chase P, Eggler A, Dawson ES, Baez-Santos YM, Tomar S, Mielech AM, Baker SC, Lindsley CW, Hodder P, Mesecar A, Stauffer SR. Discovery, synthesis, and structure-based optimization of a series of N-(tert-butyl)-2-(N-arylamido)-2-(pyridin-3-yl) acetamides (ML188) as potent noncovalent small molecule inhibitors of the severe acute respiratory syndrome coronavirus (SARS-CoV) 3CL protease. J Med Chem. 2013 Jan 24;56(2):534-46. doi: 10.1021/jm301580n. Epub 2013 Jan 3. PMID: 23231439; PMCID: PMC3569073.
In vitro protocol:
1. Lockbaum GJ, Reyes AC, Lee JM, Tilvawala R, Nalivaika EA, Ali A, Kurt Yilmaz N, Thompson PR, Schiffer CA. Crystal Structure of SARS-CoV-2 Main Protease in Complex with the Non-Covalent Inhibitor ML188. Viruses. 2021 Jan 25;13(2):174. doi: 10.3390/v13020174. PMID: 33503819; PMCID: PMC7911568. 2. Jacobs J, Grum-Tokars V, Zhou Y, Turlington M, Saldanha SA, Chase P, Eggler A, Dawson ES, Baez-Santos YM, Tomar S, Mielech AM, Baker SC, Lindsley CW, Hodder P, Mesecar A, Stauffer SR. Discovery, synthesis, and structure-based optimization of a series of N-(tert-butyl)-2-(N-arylamido)-2-(pyridin-3-yl) acetamides (ML188) as potent noncovalent small molecule inhibitors of the severe acute respiratory syndrome coronavirus (SARS-CoV) 3CL protease. J Med Chem. 2013 Jan 24;56(2):534-46. doi: 10.1021/jm301580n. Epub 2013 Jan 3. PMID: 23231439; PMCID: PMC3569073.
In vivo protocol:
TBD
1: Berry M, Fielding B, Gamieldien J. Human coronavirus OC43 3CL protease and the potential of ML188 as a broad-spectrum lead compound: homology modelling and molecular dynamic studies. BMC Struct Biol. 2015 Apr 28;15:8. doi: 10.1186/s12900-015-0035-3. PMID: 25928480; PMCID: PMC4411765. 2: Turlington M, Chun A, Tomar S, Eggler A, Grum-Tokars V, Jacobs J, Daniels JS, Dawson E, Saldanha A, Chase P, Baez-Santos YM, Lindsley CW, Hodder P, Mesecar AD, Stauffer SR. Discovery of N-(benzo[1,2,3]triazol-1-yl)-N-(benzyl)acetamido)phenyl) carboxamides as severe acute respiratory syndrome coronavirus (SARS-CoV) 3CLpro inhibitors: identification of ML300 and noncovalent nanomolar inhibitors with an induced-fit binding. Bioorg Med Chem Lett. 2013 Nov 15;23(22):6172-7. doi: 10.1016/j.bmcl.2013.08.112. Epub 2013 Sep 7. PMID: 24080461; PMCID: PMC3878165. 3: Turlington M, Chun A, Jacobs J, Dawson E, Daniels JS, Saldanha A, Chase P, Hodder P, Eggler A, Tokars V, Mesecar A, Lindsley CW, Stauffer SR. Non-covalent triazole-based inhibitors of the SARS main proteinase 3CLpro. 2012 Apr 9 [updated 2013 Mar 14]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 23762941. 4: Jacobs J, Zhou S, Dawson E, Daniels JS, Hodder P, Tokars V, Mesecar A, Lindsley CW, Stauffer SR. Discovery of non-covalent inhibitors of the SARS main proteinase 3CLpro. 2010 Oct 30 [updated 2013 Feb 28]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 23658941. 5: Jacobs J, Grum-Tokars V, Zhou Y, Turlington M, Saldanha SA, Chase P, Eggler A, Dawson ES, Baez-Santos YM, Tomar S, Mielech AM, Baker SC, Lindsley CW, Hodder P, Mesecar A, Stauffer SR. Discovery, synthesis, and structure-based optimization of a series of N-(tert-butyl)-2-(N-arylamido)-2-(pyridin-3-yl) acetamides (ML188) as potent noncovalent small molecule inhibitors of the severe acute respiratory syndrome coronavirus (SARS-CoV) 3CL protease. J Med Chem. 2013 Jan 24;56(2):534-46. doi: 10.1021/jm301580n. Epub 2013 Jan 3. PMID: 23231439; PMCID: PMC3569073. 6: Xue JH, Qian QM, Wang YS, Meng XL, Liu L. Resonance light scattering determination of metallothioneins using levofloxacin-palladium complex as a light scattering probe. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Feb;102:205-11. doi: 10.1016/j.saa.2012.10.016. Epub 2012 Oct 23. PMID: 23220658. 7: Wenning C, Stypmann J, Papavassilis P, Sindermann J, Schober O, Hoffmeier A, Scheld HH, Stegger L, Schäfers M. Left ventricular dilation and functional impairment assessed by gated SPECT are indicators of cardiac allograft vasculopathy in heart transplant recipients. J Heart Lung Transplant. 2012 Jul;31(7):719-28. doi: 10.1016/j.healun.2012.02.018. Epub 2012 Mar 14. PMID: 22425234.

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CMX-020

CMX-020