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Compound Detail

CHEMBL561643

MANGOSTANIN
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COc1c(O)cc2oc3cc4c(c(O)c3c(=O)c2c1CC=C(C)C)C=CC(C)(C)O4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL561643
Name MANGOSTANIN
Phase Preclinical
Structure Type MOL
InChI Key HQWHKELJHUFLGD-UHFFFAOYSA-N
16
Targets
19
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

408.4
MW (Da)
5.06
ALogP
6
HBA
2
HBD
89.1
PSA (Ų)
0.47
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C24H24O6
MW 408.45
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness 2.82

Activity Summary

IC50 18 meas. best 6.38
Ki 1 meas. best 5.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
3',5'-cyclic-AMP phosphodiesterase 4D
CHEMBL288
 IC50 6.38 6.38 420.0 3
HT-29
CHEMBL384
 IC50 5.8 5.8 1600.0 1
KB
CHEMBL398
 IC50 5.77 5.77 1700.0 1
MCF7
CHEMBL387
 IC50 5.72 5.72 1900.0 1
HeLa S3
CHEMBL4296436
 IC50 5.72 5.72 1900.0 1
HepG2
CHEMBL395
 IC50 5.47 5.47 3400.0 1
Sialidase
CHEMBL5189
 Ki 5.23 5.23 5900.0 1
Alpha glucosidase
CHEMBL3833502
 IC50 4.94 4.94 11400.0 1
RAW264.7
CHEMBL612557
 IC50 4.73 4.73 18600.0 1
NCI-H460
CHEMBL396
 IC50 4.71 4.71 19690.0 1
Sialidase
CHEMBL5189
 IC50 4.7 4.7 20100.0 1
MDA-MB-231
CHEMBL400
 IC50 4.68 4.68 21060.0 1
ASPC1
CHEMBL612588
 IC50 4.59 4.59 25490.0 1
SW-620
CHEMBL612262
 IC50 4.58 4.58 26140.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.58 4.58 26170.0 1
Unchecked
CHEMBL612545
 IC50 4.46 4.46 34600.0 1
Fatty acid synthase
CHEMBL4158
 IC50 4.39 4.39 40640.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.135 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 420.0 nM 6.38 Inhibition of PDE4D2 (86-413) (unknown origin) expressed in Escherichia coli BL2... 34520193
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 420.0 nM 6.38 Inhibition of recombinant PDE4D2 (86 to 413 residues) (unknown origin) expressed... 35985255
3',5'-cyclic-AMP phosphodiesterase 4D IC50 = 420.0 nM 6.38 Inhibition of human PDE4D2 (86 to 413 residues) expressed in Escherichia coli BL... 32115956
HT-29 IC50 = 1600.0 nM 5.8 Cytotoxicity in human HT-29 cells incubated for 72 hrs by MTT assay 30978023
KB IC50 = 1700.0 nM 5.77 Cytotoxicity in human KB cells incubated for 72 hrs by MTT assay 30978023
MCF7 IC50 = 1900.0 nM 5.72 Cytotoxicity in human MCF7 cells incubated for 72 hrs by MTT assay 30978023
HeLa S3 IC50 = 1900.0 nM 5.72 Cytotoxicity in human HeLaS3 cells incubated for 72 hrs by MTT assay 30978023
HepG2 IC50 = 3400.0 nM 5.47 Cytotoxicity in human HepG2 cells incubated for 72 hrs by MTT assay 30978023
Sialidase Ki = 5900.0 nM 5.23 Competitive inhibition of Clostridium perfringens neuraminidase by fluorimetry 20696581
Alpha glucosidase IC50 = 11400.0 nM 4.94 Inhibition of alpha-glucosidase (unknown origin) using p-nitrophenyl alpha-D-glu... 31860303
RAW264.7 IC50 = 18600.0 nM 4.73 Inhibition of NO production in LPS-stimulated mouse RAW264.7 cells incubated for... 31860303
NCI-H460 IC50 = 19690.0 nM 4.71 Cytotoxicity against human NCI-H460 cells assessed as inhibition of cell prolife... 24717154
Sialidase IC50 = 20100.0 nM 4.7 Inhibition of Clostridium perfringens neuraminidase by fluorimetry 20696581
MDA-MB-231 IC50 = 21060.0 nM 4.68 Cytotoxicity against human MDA-MB-231 cells assessed as inhibition of cell proli... 24717154
ASPC1 IC50 = 25490.0 nM 4.59 Cytotoxicity against human AsPC1 cells assessed as inhibition of cell proliferat... 24717154
SW-620 IC50 = 26140.0 nM 4.58 Cytotoxicity against human SW620 cells assessed as inhibition of cell proliferat... 24717154
NON-PROTEIN TARGET IC50 = 26170.0 nM 4.58 Cytotoxicity against mouse B16F10 cells assessed as inhibition of cell prolifera... 24717154
Unchecked IC50 = 34600.0 nM 4.46 Inhibition of Saccharomyces cerevisiae alpha-glucosidase using p-nitrophenyl alp... 25651042
Fatty acid synthase IC50 = 40640.0 nM 4.39 Inhibition of FAS 20817450

Literature References

PubMed DOI Target Context # Activities
26508549 10.1016/j.bmcl.2015.10.034 Isocitrate dehydrogenase [NADP] cytoplasmic 2
20696581 10.1016/j.bmc.2010.07.033 Sialidase 2
25651042 10.1021/np5008476 Unchecked 2
24717154 10.1016/j.bmcl.2014.03.047 MDA-MB-231 1
35985255 10.1016/j.ejmech.2022.114631 ADMET 1
25651042 10.1021/np5008476 Escherichia coli 1
25651042 10.1021/np5008476 Staphylococcus aureus 1
25651042 10.1021/np5008476 Bacillus subtilis 1
25651042 10.1021/np5008476 Bacillus cereus 1
24717154 10.1016/j.bmcl.2014.03.047 NON-PROTEIN TARGET 1
24717154 10.1016/j.bmcl.2014.03.047 SW-620 1
24717154 10.1016/j.bmcl.2014.03.047 ASPC1 1
19296616 10.1021/np8005953 Plasmodium falciparum 1
24717154 10.1016/j.bmcl.2014.03.047 NCI-H460 1
20817450 10.1016/j.bmcl.2010.08.061 Fatty acid synthase 1
19788289 10.1021/np900404e Tumor necrosis factor receptor superfamily member 10B 1
19839614 10.1021/np900517h Nuclear factor NF-kappa-B p105 subunit 1
19839614 10.1021/np900517h Transcription factor p65 1
19839614 10.1021/np900517h HT-29 1
19296616 10.1021/np8005953 Unchecked 1

Data from ChEMBL 36 via Core Engine