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Compound Detail

CHEMBL464825

MANGIFERIN
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O=c1c2cc(O)c(O)cc2oc2cc(O)c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464825
Name MANGIFERIN
Phase Preclinical
Structure Type MOL
InChI Key AEDDIBAIWPIIBD-ZJKJAXBQSA-N
9
Targets
13
Activities
3
Assay Types
21
PK Parameters
20
Publications
0
Known Names

Molecular Properties

422.3
MW (Da)
-0.72
ALogP
11
HBA
8
HBD
201.3
PSA (Ų)
0.19
QED
2
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H18O11
MW 422.34
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness 2.00

Activity Summary

IC50 11 meas. best 6.6
EC50 1 meas. best 5.9
Kd 1 meas. best 6.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.6 6.6 250.0 1
Unchecked
CHEMBL612545
 Kd 6.4 6.4 400.2 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.9 5.9 1260.0 1
Aldo-keto reductase family 1 member B1
CHEMBL2622
 IC50 5.5 5.5 3200.0 1
Unchecked
CHEMBL612545
 IC50 4.95 4.87 11200.0 2
Sialidase
CHEMBL5189
 IC50 4.79 4.79 16200.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.62 4.62 23800.0 1
Radical scavenging activity
CHEMBL613712
 IC50 4.46 4.46 35020.0 1
Beta-glucuronidase
CHEMBL2728
 IC50 4.42 4.42 38000.0 1
BV-2
CHEMBL614781
 IC50 4.42 4.42 38500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3799.68 ng.hr.mL-1 Rattus norvegicus
AUC 3817.5 ng.hr.mL-1 Rattus norvegicus
AUC 4322.14 ng.hr.mL-1 Rattus norvegicus
AUC 4340.84 ng.hr.mL-1 Rattus norvegicus
AUC 8934.7 ng.hr.mL-1 Rattus norvegicus
AUC 8953.44 ng.hr.mL-1 Rattus norvegicus
Cmax 1692.95 nM Rattus norvegicus
Cmax 1069.99 nM Rattus norvegicus
Cmax 4726.05 nM Rattus norvegicus
MRT 7.66 hr Rattus norvegicus
MRT 7.77 hr Rattus norvegicus
MRT 7.42 hr Rattus norvegicus
MRT 7.52 hr Rattus norvegicus
MRT 5.4 hr Rattus norvegicus
MRT 5.45 hr Rattus norvegicus
T1/2 2.47 hr Rattus norvegicus
T1/2 2.59 hr Rattus norvegicus
T1/2 2.6 hr Rattus norvegicus
Tmax 0.73 hr Rattus norvegicus
Tmax 2.89 hr Rattus norvegicus
Tmax 2.25 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Matrix metalloproteinase-9 IC50 = 250.0 nM 6.6 Inhibition of MMP9 in human U2OS cells by peptide microarray-based fluorescence ... 36122348
Unchecked Kd = 400.2 nM 6.4 Binding affinity to mangiferin receptor in rat islet cell membrane stationary ph... -
NON-PROTEIN TARGET EC50 = 1260.0 nM 5.9 Antioxidant activity assessed as protection against peroxyl radical-induced alka... 18950229
Aldo-keto reductase family 1 member B1 IC50 = 3200.0 nM 5.5 Inhibition of aldose reductase in rat lens homogenate 14510595
Unchecked IC50 = 11200.0 nM 4.95 Inhibition of Clostridium welchii neuraminidase 19660948
Sialidase IC50 = 16200.0 nM 4.79 Inhibition of Clostridium perfringens neuraminidase by fluorimetry 19285413
Unchecked IC50 = 16200.0 nM 4.79 Inhibition of Clostridium perfringens neuraminidase 18938076
Plasmodium falciparum IC50 = 23800.0 nM 4.62 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 18950229
Radical scavenging activity IC50 = 35020.0 nM 4.46 Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins 14575443
BV-2 IC50 = 38500.0 nM 4.42 Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induc... 24042007
Beta-glucuronidase IC50 = 38000.0 nM 4.42 Inhibition of beta-glucuronidase (unknown origin) 31835168

Literature References

PubMed DOI Target Context # Activities
31956052 10.1016/j.bmc.2020.115304 Human alphaherpesvirus 1 33
22859782 10.1124/dmd.112.045849 Rattus norvegicus 25
22859782 10.1124/dmd.112.045849 ADMET 18
22859782 10.1124/dmd.112.045849 Plasma 17
36122348 10.1021/acs.jnatprod.2c00626 ADMET 10
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 8
21732671 10.1021/jm2006589 NON-PROTEIN TARGET 7
36122348 10.1021/acs.jnatprod.2c00626 U2OS 5
31956052 10.1016/j.bmc.2020.115304 ADMET 4
36122348 10.1021/acs.jnatprod.2c00626 Matrix metalloproteinase-9 3
19660948 10.1016/j.bmcl.2009.07.098 Unchecked 3
21732671 10.1021/jm2006589 Plasma 3
- 10.1007/s00044-011-9697-y Unchecked 3
27466882 10.1021/acs.jnatprod.6b00381 NON-PROTEIN TARGET 2
19285413 10.1016/j.bmc.2009.02.042 Sialidase 2
24613627 10.1016/j.bmc.2014.02.014 Neuraminidase 2
24042007 10.1016/j.bmcl.2013.08.085 BV-2 2
31956052 10.1016/j.bmc.2020.115304 Unchecked 2
18938076 10.1016/j.bmcl.2008.10.033 Unchecked 2
31835168 10.1016/j.ejmech.2019.111921 Beta-glucuronidase 2

Data from ChEMBL 36 via Core Engine