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Compound Detail

CHEMBL1214186

SINEFUNGIN
🧪 Phase II
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🧪 Phase II
Nc1ncnc2c1ncn2[C@@H]1O[C@H](C[C@@H](N)CC[C@H](N)C(=O)O)[C@@H](O)[C@H]1O

Basic Information

ChEMBL ID CHEMBL1214186
Name SINEFUNGIN
Phase Phase II
Structure Type MOL
InChI Key LMXOHSDXUQEUSF-YECHIGJVSA-N

Known Names

COMPOUND 57926 LILLY 57926 LY-57926 Sinefungin Sinefungina Sinefungine
23
Targets
72
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names

Molecular Properties

381.4
MW (Da)
-2.06
ALogP
11
HBA
6
HBD
208.7
PSA (Ų)
0.31
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -fungin
USAN Year 1978

Extended Properties

Molecular Formula C15H23N7O5
MW 381.39
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 1.25

Activity Summary

IC50 65 meas. best 9.26
Kd 5 meas. best 6.87
Ki 2 meas. best 4.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
mRNA cap guanine-N7 methyltransferase
CHEMBL4295662
IC50 9.26 7.27 0.6 2
Unchecked
CHEMBL612545
IC50 7.52 6.139 30.0 21
Nonstructural protein 5
CHEMBL4295629
IC50 7.39 7.39 41.0 1
Histone-lysine N-methyltransferase EHMT2
CHEMBL6032
IC50 7.0 5.3467 100.0 3
Histone-lysine N-methyltransferase EHMT1
CHEMBL6031
IC50 7.0 5.775 100.0 2
Unchecked
CHEMBL612545
Kd 6.87 5.755 136.0 2
Replicase polyprotein 1ab
CHEMBL4523582
IC50 6.58 6.516 260.0 5
Protein arginine N-methyltransferase 5
CHEMBL1795116
IC50 6.51 5.9133 310.0 3
Leishmania donovani
CHEMBL367
IC50 6.0 6.0 1000.0 1
NS5
CHEMBL4523952
IC50 5.93 5.86 1180.0 2
METTL3/METTL14
CHEMBL4106140
IC50 5.89 5.76 1300.0 2
Protein arginine N-methyltransferase 1
CHEMBL5524
IC50 5.79 5.61 1630.0 2
Histone-arginine methyltransferase CARM1
CHEMBL5406
IC50 5.76 5.76 1750.0 1
Histone-lysine N-methyltransferase SETD7
CHEMBL5523
IC50 5.62 5.42 2380.0 3
Nicotinamide N-methyltransferase
CHEMBL2346486
IC50 5.41 5.1967 3900.0 3
Indolethylamine N-methyltransferase
CHEMBL2131
IC50 5.4 5.4 4000.0 1
tRNA (cytosine(38)-C(5))-methyltransferase
CHEMBL4523124
Kd 5.12 4.9 7500.0 2
Thiopurine S-methyltransferase
CHEMBL2500
Kd 5.0 5.0 10000.0 1
tRNA (cytosine(38)-C(5))-methyltransferase
CHEMBL4523124
IC50 4.88 4.88 13200.0 1
Genome polyprotein
CHEMBL4523307
IC50 4.72 4.72 19200.0 1
Histone-lysine N-methyltransferase, H3 lysine-79 specific
CHEMBL1795117
IC50 4.47 4.47 33710.0 1
Histone-lysine N-methyltransferase NSD2
CHEMBL3108645
IC50 4.34 4.22 46000.0 4
Histone-lysine N-methyltransferase, H3 lysine-36 specific
CHEMBL3588738
IC50 4.34 4.34 46000.0 1
Protein-L-isoaspartate(D-aspartate) O-methyltransferase
CHEMBL4240
Ki 4.33 4.33 47000.0 1
Histone-lysine N-methyltransferase NSD3
CHEMBL3108646
IC50 4.21 4.21 61000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
mRNA cap guanine-N7 methyltransferase IC50 = 0.55 nM 9.26 Inhibition of human guanine-N7 methyltransferase expressed in Saccharomyces cere... 33007557
Unchecked IC50 = 30.0 nM 7.52 Inhibition of Dengue virus N-7 methyltransferase incubated for 15 mins followed ... 33128910
Unchecked IC50 = 30.0 nM 7.52 Inhibition of Dengue virus guanine N-7 methyltransferase using RNA substrate aft... 26771861
Nonstructural protein 5 IC50 = 41.0 nM 7.39 Inhibition of Dengue virus ribose 2'-O methyltransferase using RNA substrate aft... 26771861
Unchecked IC50 = 41.0 nM 7.39 Inhibition of Dengue virus 2'-O methyltransferase incubated for 15 mins followed... 33128910
Histone-lysine N-methyltransferase EHMT2 IC50 = 100.0 nM 7.0 Inhibition of EHMT2 (unknown origin) 28739157
Histone-lysine N-methyltransferase EHMT1 IC50 = 100.0 nM 7.0 Inhibition of EHMT1 (unknown origin) 28739157
Unchecked IC50 = 112.0 nM 6.95 Inhibition of MTase activity of N-terminal 6XHis-tagged SARS-CoV-1 NSP14 express... 34257831
Unchecked Kd = 136.0 nM 6.87 Binding affinity to His-tagged Dengue virus 3 methyltransferase expressed in Esc... 26771861
Replicase polyprotein 1ab IC50 = 260.0 nM 6.58 Inhibition of MTase activity of SARS-CoV-2 NSP14 expressed in Escherichia coli B... 36097498
Replicase polyprotein 1ab IC50 = 278.0 nM 6.56 Inhibition of N-terminal hexa-histidine tagged recombinant SARS-CoV-2 nsp14 RNA ... 38516599
Replicase polyprotein 1ab IC50 = 278.0 nM 6.56 Inhibition of N7-MTase activity of SARS-CoV-2 N-terminus hexahistidine tag nsp14... 35439007
Protein arginine N-methyltransferase 5 IC50 = 310.0 nM 6.51 Affinity Biochemical interaction: (inhibition of histone H4 (1-21) methylation) ... -
Replicase polyprotein 1ab IC50 = 360.0 nM 6.44 Inhibition of N-terminal 6His-tagged SARS-CoV 2 nsp14 N7-methyltransferase activ... 37192550
Replicase polyprotein 1ab IC50 = 360.0 nM 6.44 Inhibition of SARS-CoV-2 nsp14 N7-MTase activity using [3H]SAM as substrate incu... 35439007
Unchecked IC50 = 360.0 nM 6.44 Inhibition of N7-MTase activity of N-terminal His6-tagged SARS-CoV nsp14 express... 32563813
Unchecked IC50 = 383.0 nM 6.42 Inhibition of MTase activity of SARS-CoV-1 WHU NSP14 expressed in Escherichia co... 34257831
Unchecked IC50 = 450.0 nM 6.35 Inhibition of MTase activity of N-terminal 6XHis-tagged SARS-CoV-2 NSP14 express... 34257831
Unchecked IC50 = 496.0 nM 6.3 Inhibition of MTase activity of N-terminal 6XHis-tagged SARS-CoV-1 NSP14 (5903 t... 34257831
Unchecked IC50 = 630.0 nM 6.2 Inhibition of DENV NS5-MTase domain using GpppA2'OMe-RNA74 as a substrate incuba... 34273661

Literature References

PubMed DOI Target Context # Activities
35849534 10.1021/acs.jmedchem.2c00388 tRNA (cytosine(38)-C(5))-methyltransferase 10
34257831 10.1021/acsmedchemlett.1c00140 Unchecked 7
33007557 10.1016/j.bmc.2020.115745 Unchecked 6
32563813 10.1016/j.ejmech.2020.112557 Unchecked 4
28739157 10.1016/j.bmc.2017.06.032 Histone-lysine N-methyltransferase EHMT2 4
28739157 10.1016/j.bmc.2017.06.032 Histone-lysine N-methyltransferase EHMT1 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
36581322 10.1021/acs.jmedchem.2c01789 Unchecked 3
37312859 10.1021/acsmedchemlett.3c00062 tRNA (cytosine(38)-C(5))-methyltransferase 3
26771861 10.1021/acs.jmedchem.5b01653 Unchecked 3
23981144 10.1021/jm400718n Unchecked 3
35439007 10.1021/acs.jmedchem.2c00120 Replicase polyprotein 1ab 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
34257831 10.1021/acsmedchemlett.1c00140 ADMET 2
34273661 10.1016/j.ejmech.2021.113683 Unchecked 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
32563813 10.1016/j.ejmech.2020.112557 mRNA cap guanine-N7 methyltransferase 2
33007557 10.1016/j.bmc.2020.115745 mRNA cap guanine-N7 methyltransferase 2
31265285 10.1021/acs.jmedchem.9b00413 Nicotinamide N-methyltransferase 2
1732534 10.1021/jm00079a007 Protein-L-isoaspartate(D-aspartate) O-methyltransferase 2

Data from ChEMBL 36 via Core Engine