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Compound Detail

CHEMBL498879

NICOTIFLOROSIDE
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C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(-c4ccc(O)cc4)oc4cc(O)cc(O)c4c3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL498879
Name NICOTIFLOROSIDE
Phase Preclinical
Structure Type MOL
InChI Key RTATXGUCZHCSNG-QHWHWDPRSA-N
9
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

594.5
MW (Da)
-1.39
ALogP
15
HBA
9
HBD
249.2
PSA (Ų)
0.16
QED
3
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H30O15
MW 594.52
Aromatic Rings 3
Heavy Atoms 42
NP-Likeness 1.94

Activity Summary

IC50 13 meas. best 5.47
EC50 2 meas. best 4.4
Ki 1 meas. best 4.49

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.47 4.76 3400.0 2
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 4.95 4.95 11300.0 1
Xanthine dehydrogenase/oxidase
CHEMBL1929
 IC50 4.83 4.83 14800.0 1
Neuraminidase
CHEMBL6135
 IC50 4.5 4.5 31700.0 1
Neuraminidase
CHEMBL6135
 Ki 4.49 4.49 32700.0 1
Influenza A virus
CHEMBL613740
 EC50 4.4 4.27 40100.0 2
Unchecked
CHEMBL612545
 IC50 4.39 4.305 40400.0 2
RAW264.7
CHEMBL612557
 IC50 4.38 4.36 41500.0 2
BV-2
CHEMBL614781
 IC50 4.35 4.35 44440.0 1
Sialidase
CHEMBL5189
 IC50 4.26 4.26 55500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 3400.0 nM 5.47 Antioxidant activity assessed as superoxide-scavenging activity by nitrite metho... 9461655
Aldo-keto reductase family 1 member B1 IC50 = 11300.0 nM 4.95 Inhibition of Sprague-Dawley rat lens aldose reductase 22264115
Xanthine dehydrogenase/oxidase IC50 = 14800.0 nM 4.83 Inhibition of xanthine oxidase assessed as decrease in uric acid production by s... 9461655
Neuraminidase IC50 = 31700.0 nM 4.5 Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Missi... 19729316
Neuraminidase Ki = 32700.0 nM 4.49 Noncompetitive inhibition of recombinant influenza A virus rvH1N1 A/Bervig_Missi... 19729316
Influenza A virus EC50 = 40100.0 nM 4.4 Antiviral activity against influenza A virus H1N1 A/PR/8/34 infected in MDCK cel... 19729316
Unchecked IC50 = 40400.0 nM 4.39 Inhibition of Saccharomyces cerevisiae alcohol dehydrogenase measured every 5 mi... 22377672
RAW264.7 IC50 = 41500.0 nM 4.38 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 24679441
BV-2 IC50 = 44440.0 nM 4.35 Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induc... 28165740
RAW264.7 IC50 = 45300.0 nM 4.34 Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-... 24679441
Sialidase IC50 = 55500.0 nM 4.26 Inhibition of Clostridium perfringens neuraminidase 19729316
Unchecked IC50 = 60700.0 nM 4.22 Inhibition of Streptococcus mutans OMZ65 sortase A lacking N-terminal membrane a... 25746812
Influenza A virus EC50 = 72900.0 nM 4.14 Antiviral activity against influenza A virus H9N2 A/Chicken/Korea/MS96/96 infect... 19729316
NON-PROTEIN TARGET IC50 = 88050.0 nM 4.05 Antineuroinflammatory activity in human BV2 cells assessed as inhibition of LPS-... 27623545

Literature References

PubMed DOI Target Context # Activities
24679441 10.1016/j.bmcl.2014.03.014 RAW264.7 7
27623545 10.1016/j.bmcl.2016.08.094 NON-PROTEIN TARGET 5
25769817 10.1016/j.bmcl.2015.02.048 Unchecked 3
22377672 10.1016/j.bmc.2012.02.002 Unchecked 3
15844957 10.1021/np0495985 NON-PROTEIN TARGET 2
28165740 10.1021/acs.jnatprod.6b00981 BV-2 2
19729316 10.1016/j.bmc.2009.08.036 Unchecked 2
31682126 10.1021/acs.jnatprod.9b00735 PANC-1 2
19729316 10.1016/j.bmc.2009.08.036 Neuraminidase 2
28165740 10.1021/acs.jnatprod.6b00981 C6 2
19729316 10.1016/j.bmc.2009.08.036 Influenza A virus 2
28682615 10.1021/acs.jnatprod.7b00063 Acinetobacter baumannii 2
7775983 10.1021/np50117a005 Unchecked 2
34403725 10.1016/j.bmcl.2021.128326 3T3-L1 2
22738356 10.1021/np3001317 C2C12 2
23149227 10.1016/j.bmcl.2012.10.043 BV-2 2
19729316 10.1016/j.bmc.2009.08.036 MDCK 1
19729316 10.1016/j.bmc.2009.08.036 Sialidase 1
9461655 10.1021/np970237h Xanthine dehydrogenase/oxidase 1
31810785 10.1016/j.ejmech.2019.111892 Tyrosinase 1

Data from ChEMBL 36 via Core Engine