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Compound Detail

CHEMBL462721

GLABROL
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CC(C)=CCc1cc([C@@H]2CC(=O)c3ccc(O)c(CC=C(C)C)c3O2)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL462721
Name GLABROL
Phase Preclinical
Structure Type MOL
InChI Key CUFAXDWQDQQKFF-DEOSSOPVSA-N
10
Targets
17
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

392.5
MW (Da)
5.82
ALogP
4
HBA
2
HBD
66.8
PSA (Ų)
0.63
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C25H28O4
MW 392.50
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.80

Activity Summary

IC50 13 meas. best 6.89
EC50 3 meas. best 5.44
Ki 1 meas. best 5.79

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 6.89 6.275 130.0 2
Tyrosine-protein phosphatase non-receptor type 1
CHEMBL335
 IC50 6.51 5.4133 310.0 3
Neuraminidase
CHEMBL6135
 IC50 6.29 5.5425 510.0 4
HMC1
CHEMBL4296432
 IC50 6.14 6.14 730.0 1
Unchecked
CHEMBL612545
 Ki 5.79 5.79 1630.0 1
HepG2
CHEMBL395
 IC50 5.55 5.55 2830.0 1
Streptokinase A
CHEMBL1293228
 EC50 5.44 5.44 3632.0 1
SW480
CHEMBL612544
 IC50 5.29 5.29 5150.0 1
Streptococcus
CHEMBL612313
 EC50 5.26 5.26 5435.0 1
Streptococcus sp. 'group A'
CHEMBL612389
 EC50 5.19 5.19 6400.0 1
MCF7
CHEMBL387
 IC50 5.12 5.12 7620.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 130.0 nM 6.89 Inhibition of Clostridium perfringens neuraminidase by chemiluminescence based a... 24313801
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 310.0 nM 6.51 Inhibition of recombinant human PTP1B using p-nitrophenyl phosphate as substrate... 28522265
Neuraminidase IC50 = 510.0 nM 6.29 Inhibition of Influenza A virus (A/Puerto Rico/8/1934(H1N1)) neuraminidase by ch... 24313801
HMC1 IC50 = 730.0 nM 6.14 Inhibition of A23187-induced IL-6 production in human HMC1 cells incubated for 3... 25467151
Unchecked Ki = 1630.0 nM 5.79 Displacement of [3H]flumazenil from GABA(A)-BZD receptor in Sprague-Dawley rat c... 22543233
Unchecked IC50 = 2170.0 nM 5.66 Inhibition of Clostridium perfringens neuraminidase by fluorescence based assay 24313801
HepG2 IC50 = 2830.0 nM 5.55 Cytotoxicity against human HepG2 cells assessed as reduction in cell viability a... 28522265
Neuraminidase IC50 = 3000.0 nM 5.52 Inhibition of Influenza A virus J/8178/09 neuraminidase by chemiluminescence bas... 24313801
Neuraminidase IC50 = 3060.0 nM 5.51 Inhibition of Influenza A virus (A/Hong Kong/1/1968(H3N2)) neuraminidase by chem... 24313801
Streptokinase A EC50 = 3632.0 nM 5.44 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 5000.0 nM 5.3 Inhibition of recombinant human PTP1B using pNPP as substrate after 30 mins 28140583
SW480 IC50 = 5150.0 nM 5.29 Cytotoxicity against human SW480 cells assessed as reduction in cell viability a... 28522265
Streptococcus EC50 = 5435.0 nM 5.26 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Streptococcus sp. 'group A' EC50 = 6400.0 nM 5.19 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
MCF7 IC50 = 7620.0 nM 5.12 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability af... 28522265
Neuraminidase IC50 = 14100.0 nM 4.85 Inhibition of oseltamivir-resistant Influenza A virus H1N1 B/55/08 neuraminidase... 24313801
Tyrosine-protein phosphatase non-receptor type 1 IC50 = 37500.0 nM 4.43 Inhibition of PTP1B (unknown origin) using p-nitrophenyl phosphate as substrate 24047800

Literature References

PubMed DOI Target Context # Activities
22543233 10.1016/j.bmc.2012.04.011 Mus musculus 6
24313801 10.1021/np400817j Neuraminidase 5
28140583 10.1021/acs.jnatprod.6b00783 Tyrosine-protein phosphatase non-receptor type 1 3
28522265 10.1016/j.bmc.2017.05.009 HepG2 2
28522265 10.1016/j.bmc.2017.05.009 SW480 2
28522265 10.1016/j.bmc.2017.05.009 MCF7 2
28522265 10.1016/j.bmc.2017.05.009 Tyrosine-protein phosphatase non-receptor type 1 2
24313801 10.1021/np400817j Influenza A virus 2
24313801 10.1021/np400817j No relevant target 2
24313801 10.1021/np400817j Unchecked 2
24047800 10.1016/j.bmcl.2013.08.102 Tyrosine-protein phosphatase non-receptor type 1 1
22543233 10.1016/j.bmc.2012.04.011 Unchecked 1
20022509 10.1016/j.bmc.2009.11.027 Peroxisome proliferator-activated receptor gamma 1
24313801 10.1021/np400817j MDCK 1
7381508 10.1021/np50008a004 Candida albicans 1
28140583 10.1021/acs.jnatprod.6b00783 SW480 1
7381508 10.1021/np50008a004 Mycolicibacterium smegmatis 1
7381508 10.1021/np50008a004 Klebsiella pneumoniae 1
7381508 10.1021/np50008a004 Salmonella enterica subsp. enterica serovar Gallinarum 1
7381508 10.1021/np50008a004 Escherichia coli 1

Data from ChEMBL 36 via Core Engine