| Chemical Information | |
| Antiviral agent ID | DrugRepV_4581 | |
| Antiviral agent name | 6-{[(3S,6aR,6bS,8aS,11S,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-11-{[(2S)-4-methyl-1-oxopentan-2-yl]carbamoyl}-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4-dihydroxy-N-[(2S)-4-methyl-1-oxopentan-2-yl]-5-[(3 | |
| IUPAC Name | 6-{[(3S,6aR,6bS,8aS,11S,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-11-{[(2S)-4-methyl-1-oxopentan-2-yl]carbamoyl}-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4-dihydroxy-N-[(2S)-4-methyl-1-oxopentan-2-yl]-5-[(3,4,5-trihydroxy-6-{[(2S)-4-methyl-1-oxopentan-2-yl]carbamoyl}oxan-2-yl)oxy]oxane-2-carboxamide |  |
| SMILES (isomeric) | CC(C)C[C@H](NC(=O)C1OC(OC2C(O)C(O)C(OC2O[C@H]2CC[C@@]3(C)C(CC[C@]4(C)C3C(=O)C=C3C5C[C@](C)(CC[C@]5(C)CC[C@@]43C)C(=O)N[C@@H](CC(C)C)C=O)C2(C)C)C(=O)N[C@@H](CC(C)C)C=O)C(O)C(O)C1O)C=O | |
| Molecular Formula | C60H95N3O16 | |
| Molecular Weight (g/mol) | 1114.425 | |
| InChl | InChI=1/C60H95N3O16/c1-30(2)22-33(27-64)61-50(73)46-42(69)41(68)45(72)52(77-46)79-48-44(71)43(70)47(51(74)62-34(28-65)23-31(3)4)78-53(48)76-40-15-16-58(11)39(55(40,7)8)14-17-60(13)49(58)38(67)25-36-37-26-57(10,54(75)63-35(29-66)24-32(5)6)19-18-56(37,9)20-21-59(36,60)12/h25,27-35,37,39-49,52-53,68-72H,14-24,26H2,1-13H3,(H,61,73)(H,62,74)(H,63,75)/t33-,34-,35-,37?,39?,40-,41?,42?,43?,44?,45?,46?,47?,48?,49?,52?,53?,56+,57-,58-,59+,60+/s2 | |
| Structural Information | |
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| Clinical Information | |
| Biological Information | |
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Secondary Indication | Severe acute respiratory syndrome coronavirus (SARS-CoV) NA FFM1 |   |
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Secondary Indication (Approaches) | Experimental | |
| Secondary Indication (Methods) | In-vitro | |
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Secondary Indication (Model system) [cell lines/ animal models] | Vero
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Secondary Indication (Mode of viral infection) | Adsorption
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Secondary Indication (Viral titer) | 0.01 MOI
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Secondary Indication (Mode of drug delivery) | Culture
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Secondary Indication (Time of drug delivery) | Post infection
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Secondary Indication (Duration of drug delivery) | 72 hours
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Secondary Indication (Drug concentration) | >1000 μM
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Secondary Indication (Cell based assay) | Cytopathic effect (CPE) assay
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Secondary Indication (Change) | Decrease
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Secondary Indication (Type of Inhibition) | EC50 [ 50 % ] | |
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Secondary Indication (Cytotoxicity) | >1000 μM | |
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Reference | Hoever G, Baltina L, Michaelis M, Kondratenko R, Baltina L, Tolstikov GA, Doerr HW, Cinatl J Jr..Antiviral activity of glycyrrhizic acid derivatives against SARS-coronavirus..J Med Chem. 2005 Feb 24;48(4):1256-9. PMID:15715493
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Comment | Amides of GL and conjugates of GL with two amino acid residues and a free 30-COOH function presented up to 70-fold increased activity against SARS-CoV but also increased cytotoxicity resulting in decreased selectivity index.
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