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Compound Detail

CHEMBL251254

HYPEROSIDE
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O=c1c(O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)c(-c2ccc(O)c(O)c2)oc2cc(O)cc(O)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL251254
Name HYPEROSIDE
Phase Preclinical
Structure Type MOL
InChI Key OVSQVDMCBVZWGM-DTGCRPNFSA-N
10
Targets
28
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

464.4
MW (Da)
-0.54
ALogP
12
HBA
8
HBD
210.5
PSA (Ų)
0.23
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C21H20O12
MW 464.38
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness 2.16

Activity Summary

IC50 27 meas. best 7.16
EC50 1 meas. best 4.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.16 5.88 70.0 13
Cytochrome P450 2D6
CHEMBL289
 IC50 5.92 5.92 1200.0 1
2-5A-dependent ribonuclease
CHEMBL3575
 IC50 5.88 5.8475 1320.0 4
Dengue virus
CHEMBL613757
 IC50 5.77 5.77 1700.0 1
Aldo-keto reductase family 1 member B1
CHEMBL1900
 IC50 5.52 5.52 3000.0 1
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 4.99 4.99 10280.0 1
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 4.66 4.66 21760.0 1
RAW264.7
CHEMBL612557
 IC50 4.31 4.31 48800.0 1
C2C12
CHEMBL612655
 EC50 4.22 4.22 60500.0 1
Neuraminidase
CHEMBL3559643
 IC50 4.2 4.135 62500.0 2

Pharmacokinetic Data

Parameter Value Units Species
Ke 390.0 nM Homo sapiens
Ke 9070.0 nM Homo sapiens
Ke 340.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 70.0 nM 7.16 Inhibition of Staphylococcus aureus DNA Topoisomerase 4-mediated decatenation of... 21534606
Unchecked IC50 = 100.0 nM 7.0 Inhibition of Escherichia coli DNA gyrase assessed as inhibition of pBR322 super... 21534606
Unchecked IC50 = 650.0 nM 6.19 Inhibition of P-RNAase L R353E mutant expressed in Escherichia coli BL21 (DE3) a... 34841869
Unchecked IC50 = 900.0 nM 6.05 Inhibition of wild type P-RNAase L expressed in Escherichia coli BL21 (DE3) asse... 34841869
Unchecked IC50 = 1020.0 nM 5.99 Inhibition of P-RNAase L K164E mutant expressed in Escherichia coli BL21 (DE3) a... 34841869
Cytochrome P450 2D6 IC50 = 1200.0 nM 5.92 Inhibition of human CYP2D6 preincubated for 5 min by LC-MS/MS analysis 34841869
Unchecked IC50 = 1260.0 nM 5.9 Inhibition of recombinant full length P-RNAase L (1 to 743 residues)expressed in... 34841869
2-5A-dependent ribonuclease IC50 = 1320.0 nM 5.88 Inhibition of full length H-RNAase L expressed in Escherichia coli BL21 (DE3) as... 34841869
2-5A-dependent ribonuclease IC50 = 1360.0 nM 5.87 Inhibition of full length H-RNAase L expressed in Escherichia coli BL21 (DE3) as... 34841869
Unchecked IC50 = 1420.0 nM 5.85 Inhibition of full length P-RNAase L expressed in Escherichia coli BL21 (DE3) as... 34841869
Unchecked IC50 = 1420.0 nM 5.85 Inhibition of full length P-RNAase L expressed in Escherichia coli BL21 (DE3) as... 34841869
2-5A-dependent ribonuclease IC50 = 1420.0 nM 5.85 Inhibition of full length H-RNAase L expressed in Escherichia coli BL21 (DE3) as... 34841869
Unchecked IC50 = 1470.0 nM 5.83 Inhibition of full length P-RNAase L expressed in Escherichia coli BL21 (DE3) as... 34841869
2-5A-dependent ribonuclease IC50 = 1630.0 nM 5.79 Inhibition of recombinant full length H-RNAase L (1 to 741 residues) expressed i... 34841869
Dengue virus IC50 = 1700.0 nM 5.77 Antiviral activity against Dengue virus assessed as inhibition of viral replicat... 25305334
Unchecked IC50 = 2200.0 nM 5.66 Inhibition of Trichomonas vaginalis adenosine-guanosine preferring ribohydrolase... 26592812
Aldo-keto reductase family 1 member B1 IC50 = 3000.0 nM 5.52 Inhibition of human recombinant aldose reductase using D-glyceraldehyde as subst... 22261024
Unchecked IC50 = 3070.0 nM 5.51 Inhibition of Escherichia coli DNA topoisomerase 4 subunit ParC/DNA topoisomeras... 21534606
Unchecked IC50 = 4000.0 nM 5.4 Inhibition of Trichomonas vaginalis adenosine-guanosine preferring ribohydrolase... 26592812
Cyclin-dependent kinase 5/CDK5 activator 1 IC50 = 10280.0 nM 4.99 Inhibition of CDK5/p25 (unknown origin) after 30 mins by SDS-PAGE analysis 23927974

Literature References

PubMed DOI Target Context # Activities
21428416 10.1021/np200001x Mus musculus 23
34841869 10.1021/acs.jmedchem.1c01156 Unchecked 8
24679441 10.1016/j.bmcl.2014.03.014 RAW264.7 7
25862199 10.1016/j.bmcl.2015.03.058 No relevant target 6
21534606 10.1021/jm200010x Staphylococcus aureus 6
20408551 10.1021/np1000329 Rattus norvegicus 5
34841869 10.1021/acs.jmedchem.1c01156 2-5A-dependent ribonuclease 5
8350094 10.1021/np50096a018 Platelet 4
10479312 10.1021/np9900674 Radical scavenging activity 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37252098 10.1039/d3md00078h Solute carrier organic anion transporter family member 2B1 4
22578462 10.1016/j.bmcl.2012.04.081 Unchecked 3
21534606 10.1021/jm200010x Unchecked 3
8350094 10.1021/np50096a018 Aorta 3
26592812 10.1016/j.bmcl.2015.10.030 Unchecked 3
25096296 10.1016/j.bmcl.2014.07.010 Neuraminidase 2
25397870 10.1021/np500231g NON-PROTEIN TARGET 2
- 10.1007/s00044-010-9391-5 Radical scavenging activity 2
24679441 10.1016/j.bmcl.2014.03.014 Bifunctional epoxide hydrolase 2 2
21354800 10.1016/j.bmc.2010.12.043 Broad substrate specificity ATP-binding cassette transporter ABCG2 2

Data from ChEMBL 36 via Core Engine